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Holiday Rentals near Duval Street

Duval Street, Key West, Florida 33040
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    Travellers to Key West are booking March dates now. Secure your holiday rental today, and have the perfect trip.
    All 99 Rentals in Key West
    1/2 Block to Duval, World of its own -Nassau Suite1 / 17
    (42)Excellent
    0.3 kilometres from Duval Street
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Center of It All - Paradise Island Suite1 / 14
    (40)Very good
    0.3 kilometres from Duval Street
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Best Location, 1/2 Block to Duval, Bimini Suite1 / 68
    (54)Very good
    0.3 kilometres from Duval Street
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Steps to Duval, Old Town Charm -Grand Bahama Suite1 / 22
    (75)Very good
    0.3 kilometres from Duval Street
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Wi-Fi
    • Outdoor Dining Area
    • Air Conditioning
    • Balcony
    • Parking
    • Washer
    • Grill
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    Awesome place to stay. Shows just like the pictures! Very close to everything. Grocery 1 block over as well as a great pizza place. 4 different units so you have to share the...
    Reviewed 4 weeks ago
    Our family had a great vacation. It was wonderful to return to the quiet house after a full day of Key West fun.
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    About this property
    Just steps away from shops, restaurants, and the excitement of Duval Street, yet set on a quiet side street in a world of its own. With 3 bedrooms and 2 Baths, The Grand Bahama Suite has plenty of room for a large gathering or group of friends. Experience endless sunshine and the incomparable...
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    Key West, Florida Keys
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Key West home w/shared pool and just steps from historic Old Town1 / 58
    (1)Excellent
    0.4 kilometres from Duval Street
    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    • DVD Player
    • Grill
    • Cable/satellite TV
    • Balcony
    • Wi-Fi
    • Air Conditioning
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bright Key West Beauty This perfectly positioned rental with access to a shared pool puts you close to everything in Key West, so bring the whole family for a memorable tropical retreat. Situated in the premiere gated community of Truman Annex, this home is just steps from historic Old Town....
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    Stock Island, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 5
    Recently renovated home w/ shared pool, furnished patio area - in town, dogs ok1 / 28
    (2)Very good
    0.2 kilometres from Duval Street
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Cable/satellite TV
    • Air Conditioning
    • Patio
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 October 2018
    We were very pleased to locate this little home with a shared pool in the heart of the historic district. We were a group of 4 so we were looking for a clean, comfortable, and...
    Reviewed 8 March 2017
    Clean, quaint, and comfortable. The office help was great, and cleaning service was good. This is close to all of the action while maintaining a peaceful night's sleep.
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    About this property
    Poolside Retreat Up to four guests can enjoy all the fun of Key West at this updated home complete with a shared pool with waterfall, and lush, outdoor seating area. As an added bonus, this home comes with private, off-street parking for one vehicle - a real luxury in the Keys! Dogs are allowed...
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    Stock Island, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    0.3 kilometres from Duval Street
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Terrace
    • Hot Tub
    • Balcony
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Dreaming of a quiet tropical vacation in a luxurious town home with an equipped kitchen? Our residence is the place for you! Offering a relaxing location away from the hustle and bustle, our guests will enjoy access to three outdoor pools, daily breakfast, housekeeping, air conditioning, and more...
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    Stock Island, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    0.3 kilometres from Duval Street
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Hot Tub
    • Balcony
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Dreaming of lazing in a hammock surrounded by palm trees? Our residence is the place for you! Offering a relaxing location away from the hustle and bustle, our guests will enjoy access to three outdoor pools, daily breakfast, housekeeping, air conditioning, and more when they stay here. • 2 Queen...
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    Stock Island, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    0.3 kilometres from Duval Street
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Hot Tub
    • Air Conditioning
    • Balcony
    • Terrace
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spend your holiday amid luxury when you stay in our suite that has a spiral staircase, a large private courtyard, original artwork, and air conditioning. Offering a relaxing location away from the hustle and bustle, our guests will enjoy access to three outdoor pools, daily breakfast, housekeeping,...
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    Stock Island, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    0.3 kilometres from Duval Street
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Hot Tub
    • Balcony
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Dreaming of a quiet tropical vacation surrounded by palm trees? Our residence is the place for you! Offering a relaxing location away from the hustle and bustle, but close enough to partake in all the activities that Key West has to offer, our guests will enjoy access to three outdoor pools, daily...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Heart of Old Town getaway, perfect romantic retreat -near the action1 / 26
    (1)Excellent
    0.3 kilometres from Duval Street
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 August 2019
    It's not big, but it's plenty for two people. The a/c unit was sufficient, the bed a little squeaky but comfortable, bathroom small but sufficient. Everything was clean and...
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    About this property
    Truman * Duval - Studio A Suprise your special someone with a stay at this charming and colorful Key West retreat! Set right in the heart of downtown, this home offers the perfect opportunity to enjoy a sun-kissed vacation you'll never forget. Located steps from the intersection of Truman Avenue...
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    Stock Island, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
    Couple's dog-friendly getaway with central location and access to a shared pool1 / 26
    (39)Very good
    0.3 kilometres from Duval Street
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Wi-Fi
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 March 2015
    I cannot say enough great things about this place. There are 6 duplexes totaling 12 2 story cottages. In the center of all the cottages is a communal area considering of a...
    Reviewed 1 March 2015
    The pictures of the Bermuda Suite are better than the reality, but it is not bad. It is in a gated courtyard complex and the location is ideal. We were able to walk everywhere...
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    About this property
    Old Town Garden Villas - Bermuda Suite Book your romantic escape to this dog-friendly Key West home. With access to a shared pool and a great location on Duval Street, you'll be able to slip into vacation mode in no time. Notice: This is in a residential area, Quiet Hours are 10:00pm- 8:00am...
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    Stock Island, Florida Keys
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
    Contemporary beachside escape with shared pool and close to local attractions1 / 25
    (4)Very good
    0.4 kilometres from Duval Street
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Patio
    • Shared Outdoor Pool (Unheated)
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 March 2014
    We had a wonderful time staying in Key West. The condo location was perfect. We walked everywhere. The beds were comfortable, and although the kitchen is very small, it was...
    Reviewed 12 March 2014
    This place is a very nice place to stay.Key West Vacation Rentals are very helpful and easy to reach.The location is perfect just 5 minutes walk to Duval Street and 15 min to...
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    About this property
    Lazy Lane at Shipyard Condos Grab your sunglasses, bathing suit, and sunscreen and get ready to dive into the beach lifestyle when you book this Key West condo. Boasting a shared pool to stay cool, this home gives you the chance to slip into vacation mode with ease. This condo is just two...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Contemporary dog-friendly cottage with easy beach access and shared pool1 / 31
    (33)Very good
    0.3 kilometres from Duval Street
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 August 2017
    We LOVED our stay at the Andros Suite! The condo itself was clean and comfortable. The courtyard was breathtaking! The couple that are the property managers are PHENOMENAL...
    Reviewed 20 May 2016
    We loved our stay at the Andros Suite. The unit was very comfortable. They even had daily service who came in and cleaned and provided fresh towels (which was unexpected...
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    About this property
    Old Town Garden Villas - Andros Suite Book your well-deserved getaway to this dog-friendly Key West home. With a prime central location near Duval Street and access to a shared pool, this home will let up to four guests and your happy puppy (for a small nightly fee) unwind in style. Notice:...
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    Stock Island, Florida Keys
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
    Two-level dog-friendly cottage w/shared pool, outdoor shower - near the beach1 / 33
    (20)Very good
    0.3 kilometres from Duval Street
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Washer
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 October 2015
    This is our second year at this location. This year we chose the Havana Suite. The unit was extremely clean and pleasantly decorated. Very nice kitchen. TVs in the bedroom and...
    Reviewed 27 April 2015
    We chose Little Havana initially because of the location. It is a smidgen off the beaten path from the hustle and bustle of the Duval action, yet within walking distance to a...
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    About this property
    Old Town Garden Villas - Little Havana Suite Slip into vacation mode at this dog-friendly Key West cottage. Featuring room for up to four people, two levels, a shared pool, and easy access to all of the seaside action, this home promises to make your next vacation fun-filled and hassle-free!...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
    0.3 kilometres from Duval Street
    Studio, 2 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Truman * Duval - Unit B Enjoy this one bedroom apartment for your next getaway to Key West! Perfect for couples, this romantic spot is newly remodeled and will provide everything you need for a quick weekend escape! Beach towels are provided for your use. What's nearby: Located in the heart of...
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    Stock Island, Florida Keys
    Condo/Apartment - 2 Bathrooms, Sleeps 4
    Romantic dog-friendly cottage w/shared pool, tropical decor, & easy beach access1 / 19
    (25)Excellent
    0.3 kilometres from Duval Street
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 October 2014
    Pictures are awesome and still don't do this unit justice. It is fabulous. Located midway between Southernmost point and Mallory Square, half block off Duval. You can get...
    Reviewed 19 August 2014
    My husband and I had an awesome time in this villa. It's the perfect location, so close to all the hot spots. The Caribbean Suite was very cute and clean. The decor was fun and...
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    About this property
    Old Town Garden Villas - Caribbean Suite Book your romantic retreat to this dog-friendly Key West cottage. Enjoy the shared pool and a great location off of Duval Street. Notice: This is in a residential area, Quiet Hours are 10:00pm- 8:00am Located a few blocks from the Florida Keys...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
    Cozy, dog-friendly cottage w/ patio - walk to shops, restaurants, and more!1 / 25
    (29)Very good
    0.3 kilometres from Duval Street
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Patio
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 May 2016
    Beautiful room, stocked kitchen, comfortable bed, private front porch. Loved everything about it! We only stayed one night but we could have stayed a month!
    Reviewed 13 July 2015
    Can't say enough about this place. Will never stay at another location in Key West. Staff was kind and helpful. Felt like this place was my own home, very cozy. Highly recommend.
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    About this property
    Truman Suite Enjoy the tropical ambience of this studio-style Key West cottage, where you'll find a private patio, dog-friendly accommodations, and a perfect location for dining, shopping, and exploring the local beaches and nightlife. This sweet yellow cottage is located in a small complex that...
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    Location Information
    Stock Island, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
    0.3 kilometres from Duval Street
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Patio
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Cool Breeze *Please note that this home only allows minimum night stays of 7 nights or longer. This is enforced by the HOA and we cannot make any exceptions. You will love this charming townhome that is located on the President's Walk in the Truman Annex, Key West's most exclusive gated...
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    Location Information
    Stock Island, Florida Keys
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Dog-friendly, colorful cottages w/ pool & hot tub in a fabulous location!1 / 44
    (14)Excellent
    0.3 kilometres from Duval Street
    5 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Washer
    • Hot Tub
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 January 2015
    Three generations, nine people, stayed here over Christmas. We each had space to be by ourselves, and we all had space to get together. Nine of us sat around the table in the...
    Reviewed 3 September 2014
    I came to the Almost Southernmost Retreat for my friends bachelorette party for Labor Day weekend 2014. We had 12 girls and there was more than enough room for everyone. This...
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    About this property
    Almost Southernmost Retreat A large group getaway to Key West starts with this pair of charming cottages, which feature a total five bedrooms, three-and-a-half bathrooms, and a max occupancy of 16. The property also includes a private heated swimming pool, a private hot tub, and dog-friendly...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 14
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    Centrally located home w/ private pool 3 blocks to Duval St - dogs OK!1 / 25
    (9)Very good
    0.3 kilometres from Duval Street
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Grill
    • Patio
    • Private Outdoor Pool (Unheated)
    • Washer
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 March 2016
    We spent January and February at Casa 625 and loved it. There were definitely some issues with the house when we arrived, but once Rick, the rental property manager, got...
    Reviewed 23 December 2013
    The house is my perfect idea of what a Key West Conce Cottage should be. With Dade County pine walls, heated pool, all modern conveniences and perfect location for quite and...
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    Casa 625 *Please note that this home only allows minimum night stays of 28 nights or longer. This is enforced by the HOA and we cannot make any exceptions.* Swim in the private pool, head to downtown Key West to soak up the sights, or relax in a breezy dog-friendly home - with this amazing...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Four condos w/ entertainment, private parking & beach nearby - great for groups!1 / 24
    (2)Very good
    0.2 kilometres from Duval Street
    4 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Balcony
    • Patio
    • Cable/satellite TV
    • Air Conditioning
    • Terrace
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 July 2014
    Lovely we'll maintained, self catering, semi-detached apartments which allows privacy yet accommodates large extended family barbecues and mingling. We hired 3 of the apartments...
    Reviewed 29 July 2014
    Pictures online are great and the property was perfect for 3 families traveling together. We tried not to be in rooms during the day since we were busy with excursions but the...
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    About this property
    Four Flowers Guesthouse Looking for a place in sunny Key West where your whole group can bask in the pleasures of island life without sacrificing privacy? This complex of four condos is your ticket - featuring entertainment, private parking, and beach access nearby, you'll have everything you could...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 14
    Restored historic home w/ private pool & reserved off-street parking - Dogs OK!1 / 24
    (1)Excellent
    0.2 kilometres from Duval Street
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Washer
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Private Garden
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 February 2017
    My family and 2 of our friends joined us on this trip. The property was clean and close to absolutely everything. We could not have asked for a better place to stay.
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    About this property
    Bahama Dreaming Start planning your Key West vacation when you book this three-bedroom, two-bathroom home. Up to eight guests will spend their vacation days lounging by the private pool, strolling the streets of downtown, and soaking up the Florida sun on soft sand beaches. The family dog is also...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Elegant condo w/ entertainment & private parking - great central location!1 / 29
    (25)Very good
    0.2 kilometres from Duval Street
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Terrace
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 July 2015
    We found this place very cozy and well located. It was clean and very spacious for two people. The air conditioner wall was a little noise, but it didn't bother us much because...
    Reviewed 5 June 2015
    More space than a hotel room for less money than we usually pay. Convenient location to Duval. Quiet neighborhood. No closet door, beads hanging instead. When air...
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    About this property
    Orchid Suite Breathe the fresh ocean air and gaze upon tropical sunsets on your next trip to Key West with this one-bedroom, one-bathroom condo. You'll enjoy entertainment, private parking, and a great central location that lets you make the most of your vacation. Part of a complex with three...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    0.1 kilometres from Duval Street
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Private Garden
    • Cable/satellite TV
    • Washer
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Blue Pelican *Please note that this home requires minimum stays of 28 nights or longer. This is enforced by the HOA and we cannot make any exceptions. You'll be mere steps from dining, shopping, nightlife, and a wide variety of attractions at this darling Key West home, perfectly situated on...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Historic, dog-friendly cottage in the heart of Key West w/ private hot tub1 / 36
    (16)Very good
    0.3 kilometres from Duval Street
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Patio
    • Washer
    • DVD Player
    • Hot Tub
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 June 2016
    This house had a wonderful location. It was very easy to walk to Duval Street and the Southernmost Point. The beds were comfortable, but the house inside and out needs...
    Reviewed 1 July 2014
    Our first visit to the Keys celebrating our 28th anniversary with our adult children, (3 couples) this historic cottage slept all 6 of us very comfortably; in fact, the most...
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    About this property
    Almost Southernmost If you're looking for a convenient home base for your Key West adventure, consider this two-bedroom, one-bathroom vacation rental. Up to six guests will enjoy the convenient location, a private hot tub, a fully equipped kitchen, and more! The family dog is also welcome to join...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    0.1 kilometres from Duval Street
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Air Conditioning
    • Washer
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Key Lime Calypso Bask in the tropics of Key West at this dog-friendly cottage with a private heated pool and a lush backyard garden. This lovely cottage is located in Old Town near Duval Street, minutes from restaurants, museums, and the daily sunset celebration at Mallory Square. Stay cool...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    A Key West gem w/ a private pool - close to shops & restaurants, dog-friendly1 / 25
    (13)Very good
    0.1 kilometres from Duval Street
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 July 2017
    We visit Key West every couple years and stay in a different rental house each trip. This time we chose Helen's Hideaway, because A) it is a minute walk to Duval Street and B...
    Reviewed 7 June 2016
    Absolutely loved the place. We were a group of 5 girls and we found the villa really comfortable, spacious, clean and well stocked with towels, toiletries and kitchen...
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    About this property
    Helen's Hideaway Escape to Key West with the family at this charming Floridian home on a quiet street with a furnished patio, private, heated swimming pool, and space for up to six guests and a dog for a small nightly fee. This home also offers off-street, private parking for one vehicle. Two dogs...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Quaint romantic cottage with street parking, close to the beach & adventure!1 / 24
    (49)Very good
    0.4 kilometres from Duval Street
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 January 2016
    My 8 friends and I stayed here this last week and had a great time. It's directly off duval and has three king beds with a pullout couch. The beds were very comfortable while...
    Reviewed 2 December 2015
    Right in the heart of Duval and nicely tucked away from the street. Rental was very clean and orderly however it did have a strong musty smell so we purchased multiple air...
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    About this property
    Hemingway's Shadow *Please note that this home only allows minimum night stays of 28 nights or longer. This is enforced by the HOA and we cannot make any exceptions.* Whisk your special someone away for a tranquil retreat when you book your next vacation at this Key West cottage. Putting you...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Renovated home w/ shared pool & furnished patio - near Duval Street, dogs ok1 / 27
    (11)Very good
    0.2 kilometres from Duval Street
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Balcony
    • Terrace
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 July 2016
    Close to where we want to be. Have booked this place twice in two years. And plan to rent again for our annual trip.
    Reviewed 16 May 2015
    I stayed here with four of my friends and the location was wonderful close to restaurants close to clubs and only a half a block off of Duval. this is a wonderful place and I...
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    About this property
    Poolside Suite This cozy Key West rental comes with a shared pool (complete with a cascading waterfall), a furnished patio area, and space for up to six guests. It's perfect for that next family vacation or tropical getaway with a few friends. Please note that this home also comes with one private,...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Cozy, dog-friendly townhouse w/ shared pool & courtyard - walk to Duval & more!1 / 26
    (24)Very good
    0.3 kilometres from Duval Street
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Wi-Fi
    • Air Conditioning
    • Washer
    • Patio
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 May 2017
    What a beautiful place, the court yard was unbelievable all the love and care that has gone into all the plants, so peaceful to sit and relax and regroup from the Key West...
    Reviewed 1 June 2016
    Secure, gated community. Each unit was part of a duplex/townhouse. Close to Duval Street without all the noise. Home was clean and very spacious. Tons of drawer space...
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    About this property
    Old Town Garden Villas - Abaco Suite Whisk your special someone off to this enchanting Key West townhouse. Enjoy the shared pool and courtyard. The family dog is also welcome to join you for an additional nightly fee. Notice: This is in a residential area, Quiet Hours are 10:00pm- 8:00am...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Cute dog-friendly tropical condo close to attractions w/a pristine shared pool1 / 27
    (6)Very good
    0.3 kilometres from Duval Street
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Patio
    • Grill
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 January 2014
    Great lodging! Beautifully decorated and maintained, amenities way beyond what is expected! Would highly recommend staying here!
    Reviewed 5 December 2011
    First let me say that management was very accomodating. The location of the apartment is excellent and within a short walking distance of nearly everything. The apartment is...
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    About this property
    Paradise Suite *Please note that this home only allows minimum night stays of 28 nights or longer. This is enforced by the HOA and we cannot make any exceptions.* This dog-friendly cottage includes street parking, a shared pool, and a location near Duval Street. Nestled in a quiet...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
    0.3 kilometres from Duval Street
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Grill
    • Patio
    • Wi-Fi
    • Hot Tub
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Hemingway's View This turn-of-the-century Key West vacation rental is ready and waiting to be your home away from home for your next family getaway. Spacious enough for up to eight guests and a dog (for a small nightly fee), this home comes with a tropically-landscaped back yard and a private,...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Cheery beach getaway near local attractions, w/shared pool & easy beach access1 / 56
    (8)Very good
    0.3 kilometres from Duval Street
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    other travellers have booked this property
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    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Terrace
    • Balcony
    • Air Conditioning
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 September 2014
    Highly recommend this facility to anyone who is looking for a conveniently located, quiet, easily acessable 2 bedroom / 2 bath condo. Our week stay was everything we could...
    Reviewed 12 May 2014
    Three friends that I have known since first grade and I traveled to Key West for a week to celebrate the year we all turn 60. Stayed at Shipyard Perch. it was perfect. The 2...
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    About this property
    Shipyard Perch Treat yourself to a stress-free vacation filled with sun-soaked days when you book your trip to this Key West condo. With room for up to four guests to a shared pool and beach lifestyle, this home will make it easy to slip into vacation mode! Located in the Truman Annex, a quick...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    0.3 kilometres from Duval Street
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    other traveller has booked this property
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    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Truman * Duval - Two Bedroom This two-bedroom, one-bathroom house is the perfect place for your next family vacation to the palm-tree paradise of Key West! With a great location downtown, a private parking space, and easy access to a sandy beach nearby, you'll be all set for fun in the sun....
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    0.3 kilometres from Duval Street
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Wi-Fi
    • Terrace
    • Air Conditioning
    • Patio
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Truman * Duval - One Bedroom Bring some sunshine and fresh ocean air into your next romantic getaway with this cozy Key West home. You'll enjoy a great location right at the center of the action, with a uniquely decorated and vibrant atmosphere awaiting you back at home! Right off Truman Avenue,...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Charming cottage w/ private hot tub - 1 block from Duval, dogs OK!1 / 27
    (12)Very good
    0.2 kilometres from Duval Street
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
    • DVD Player
    • Hot Tub
    • Patio
    • Air Conditioning
    • Cable/satellite TV
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 January 2016
    The location is awesome. The kitchen lay out is a train wreck! It was clean and daily towel and linen and linen service was good. Parking ....good luck. Overall it was a fair...
    Reviewed 5 June 2014
    Superb location, ideal for a few days in Key West. Only small but great outside space. Loads of character, only slight negative is the bathroom could do with a little tlc. But...
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    About this property
    Conch Casa Experience Key West in style with this dog-friendly vacation rental in the heart of Old Town! Up to six guests will enjoy a private hot tub and typical home comforts including a private washer/dryer, street parking, and free WiFi. Situated just one block from Duval Street, this...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    0.2 kilometres from Duval Street
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    other traveller has booked this property
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    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Balcony
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Gardenia Getaway Ease into the pleasures of a tropical vacation with this one-bedroom, one-bathroom condo in Key West. With a charming atmosphere, entertainment, and four private parking spaces to save you any headaches, you'll speak nothing but praise during your stay in paradise! Located in...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    0.2 kilometres from Duval Street
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sky Loft This newly renovated, one bedroom, one bathroom unit comfortably sleeps four guests. From the moment you walk in, you will be amazed by the detail, decor and furnishings. The perfect rental home for those who wish to be just above all the action! You and your guests will enjoy the spacious...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 1 Bathroom, Sleeps 2
    Two rustic cottages w/ private hot tubs & private parking - dogs OK1 / 44
    (3)Very good
    0.2 kilometres from Duval Street
    4 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • Grill
    • Hot Tub
    • Wi-Fi
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 July 2014
    Tradewinds was the perfect place for 6 cousins to stay as we gathered in KW to send my sister's ashes off into her beloved warm ocean. The accommodations were perfect for the 6...
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    About this property
    Tradewinds Rustle up your favorite people for a memorable trip to Key West with these two homey cottages. Sitting side-by-side in a great location, each house features two bedrooms and one bathroom, a private parking space, dog-friendly accommodations, and a tranquil garden with a private hot tub...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 12
    Cozy cottage w/ porch & great walking location - close to beach, small dogs OK!1 / 29
    (22)Very good
    0.3 kilometres from Duval Street
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Patio
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 February 2017
    We stayed at this cottage for a couple nights. It was cozy and well kept. The kitchen had everything you'd need to cook an average meal. The cottage definitely could have used a...
    Reviewed 8 December 2014
    The home was clean, centrally located. Also, safe. will be coming back and using you guys again on our next trip to key west!
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    About this property
    Audubon House Enjoy your very own piece of Key West at this one-bedroom cottage, a lovely little home with dog-friendly accommodations, a charming front porch, and an ideal location close to restaurants, nightlife, and white sand beaches. You'll find this cheerful cottage in a small complex...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
    Historic, dog-friendly home w/ pool & two hot tubs in an unbeatable location!1 / 53
    (1)Very good
    0.1 kilometres from Duval Street
    5 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
    other traveller has booked this property
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    Amenities & Details
    • Patio
    • Hot Tub
    • Washer
    • Wi-Fi
    • Grill
    • Cable/satellite TV
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 May 2015
    We took over the whole compound with three generations of our family - my family and 4 month old twins in the attic suite, my sister's family and the grandparents on the first...
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    About this property
    Southern Palms Privacy, luxury, and convenience combine in this charming Key West vacation rental. Your large group will enjoy top-shelf amenities including a private, seasonally heated pool and two hot tubs, in addition to home comforts such as a private washer/dryer, cable, and free WiFi. This...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 14
    0.3 kilometres from Duval Street
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Olivia Street Retreat *Please note that this home only allows minimum night stays of 28 nights or longer. This is enforced by the HOA and we cannot make any exceptions. If Key West is on your itinerary, make this welcoming, conveniently located one-bedroom home yours and enjoy comfort and the...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Bright condo w/ homey feel, entertainment & private parking - beach nearby!1 / 27
    (27)Very good
    0.2 kilometres from Duval Street
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Wi-Fi
    • Balcony
    • Air Conditioning
    • Terrace
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 September 2015
    Clean and pleasant apartment. Only a couple blocks from Duval and close also to the pool provided by the rental company. Pull out bed was not comfortable, but the master bed...
    Reviewed 25 December 2014
    We only stayed 3 nights and it was the perfect location. The room was clean with all necessities needed. We didn't go to the pool but enjoyed being in walking distance to the...
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    About this property
    Jasmine Suite Slip into island time at this one-bedroom, one-bath condo for four in Key West, where you'll have entertainment and nearby beach access in an awesome central location. Sitting right downtown on Simonton Street, you're one street over from all the restaurants and bars on Duval, and...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Dog-friendly cottage w/ private hot tub & garden - great downtown location!1 / 30
    (8)Very good
    0.2 kilometres from Duval Street
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Wi-Fi
    • Hot Tub
    • Air Conditioning
    • Patio
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 July 2016
    Our only wish is for additional air conditioning units in living area and bathroom.Everything else was wonderful
    Reviewed 21 July 2014
    Very nice place, beds were super comfy. Close to Duval but quiet. This place does have a parking spot, but we were not told about it until I called.
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    About this property
    Windward Isle Dreaming about a tropical vacation? This two-bedroom, one-bathroom cottage in Key West is the perfect destination - a private hot tub, garden, and a great location downtown will make this your best vacation yet! Located only half a block from the restaurants and bars on Duval...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Studio condo w/ entertainment, full kitchen & private parking - central location1 / 23
    (27)Very good
    0.2 kilometres from Duval Street
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Patio
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 October 2015
    Loved this condo for our Keys getaway!! This place was perfect for our 5 day getaway and it's just 2 blocks from Duval. Very easy check in process took maybe 5 min at the most...
    Reviewed 20 August 2015
    We have stayed at Courtney's Place and another place farther down on Duval in the past. Hibiscus is closer to the "action" on Duval. Hibiscus is a unit for 2 people...
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    About this property
    Hibiscus Hideaway Relaxation will come easy at this studio condo in Key West. With a calming interior, entertainment, and an awesome location with a private parking spot (with off-street parking) close to all the action, this getaway will be one to remember! Located in a historic building just...
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    Location Information
    Stock Island, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
    Casa Del Sol, a Key West Vacation (Truman Annex)1 / 26
    (83)Excellent
    0.4 kilometres from Duval Street
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
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    • Air Conditioning
    • DVD Player
    • Washer
    • Grill
    • Internet Access
    • Cable/satellite TV
    • Patio
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 January 2020
    We stayed at Casa Del Sol over New Year's Eve as a family of 4. The townhouse was just as advertised, well appointed in a wonderful location. The weather was beautiful and we...
    Reviewed 29 December 2019
    The location is fantastic. It is walking distance from so many restaurants, places to see and of course Duvall St. which is only 2-3 blocks away. The condo is beautiful. From...
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    About this property
    Welcome to Casa Del Sol, a Key West Vacation...your very own luxurious and elegantly appointed 2 bedroom and 2.5 bath townhome with private carport... part of 45 lushly landscaped acres in Truman Annex. As part of President's Walk townhomes in gated Truman Annex, this premier waterfront community...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    0.1 kilometres from Duval Street
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Air Conditioning
    • Secure Parking
    • Wi-Fi
    • Cable/satellite TV
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Key West and the Shipyard section of the Truman Annex. You have many choices of accommodations since I am not a real estate salesman or property manager allow me let the photos speak for themselves. My oversized two bedroom, one bathroom condominium is located on picturesque Southard...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    President's Walk1 / 26
    (1)Excellent
    0.3 kilometres from Duval Street
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Terrace
    • Grill
    • Wi-Fi
    • Balcony
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Hot Tub
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 June 2017
    This place was perfect for the three adults and infant. The proximity to the pool, Duval St., and Green Parrot really made this beautiful condo ideal for a long Key West trip...
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    About this property
    It wasn't that long ago that President Truman took casual walks in this same location- now it's your turn! President's Walk exudes luxury and elegance with lots of upgrades and plush furnishings with your every comfort in mind. Situated directly in front of one of the community pools in the...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    6 bedroom Duval Street Compound - Pool, Hot Tub, 2 parking spots - A++ Location1 / 28
    (3)Excellent
    0.1 kilometres from Duval Street
    6 Bedrooms, 7 Bathrooms, Sleeps 16 Quick View
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    • Patio
    • Internet Access
    • Private Outdoor Pool (Unheated)
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    • DVD Player
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Private Home, DownTown, Villa description Perfect location and great for entertaining! In the heart of Old Town Key West just steps from restaurants, bars, theatres and shops, this sprawling six bedroom, seven bath compound has two private heated swimming pools, endless porches, terraces and a...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 16
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