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    67 Matching Rentals in Stock IslandView all 250 rentals
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    Heart of Old Town getaway, perfect romantic retreat -near the action1 / 26
    (1)Excellent
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    Studio, 1 Bathroom, Sleeps 2 Quick View
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    Deluxe, ground-floor studio w/ view of the courtyard and pool - close to shops1 / 26
    (14)Very good
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
    • DVD Player
    • Terrace
    • Washer
    • Wi-Fi
    • Cable/satellite TV
    • Ocean Views
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sunset at Harbour Place Enjoy this spectacular condo with an oceanfront view of Key West harbor for your next getaway in the Key West! Located in Truman Annex, this home boasts beautiful water views from the balcony and all around the condo, you'll be sure to feel inspired during your stay! This...
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    33040, Stock Island, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Curry House Room 5 Experience a piece of Key West's past when you book a stay at this charming ground-floor suite in the historic Curry House Bed & Breakfast! Up to two guests will enjoy a shared on-site pool, home comforts, and a convenient location in the heart of the city. Curry House sits...
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    33040, Stock Island, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
    Romantic & elegant studio-style cottage w/ private hot tub - dog-friendly!1 / 26
    (3)Very good
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 May 2016
    As far as the accommodation is concerned, the location is unsurpassed. The cottage is clean, comfortable and well appointed. Sadly what let's the place down are the...
    Reviewed 11 November 2015
    This is the second time we've stayed in this rental complex. The first time upstairs and now this time in the back. The location off of Whitehead is perfect for everything we...
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    About this property
    Royal Palm Experience the best of Key West from the comfort of this charming studio-style cottage. A private hot tub, dog-friendly accommodations, and modern conveniences including free WiFi and a shared washer/dryer make this vacation rental perfect for everything from a laid-back retreat to an...
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    33040, Stock Island, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Balcony
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Curry House Room 2 Experience a piece of Key West history when you rent this charming Curry House suite, which features a private en suite bathroom, a semi-private balcony, a shared pool, and room for up to two guests! Located in a quiet neighborhood three blocks from Duval Street, Curry House...
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    33040, Stock Island, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
    Studio, 2 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
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    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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    33040, Stock Island, Florida Keys
    Condo/Apartment - 2 Bathrooms, Sleeps 4
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Waterfront
    • DVD Player
    • Ocean Views
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Atlantic Parrot This beachfront condo in Key West offers a much-needed pop of color to your Florida Keys vacation! You'll enjoy views of the ocean from your private balcony, as well as an open floor plan that provides ample space for everyone to relax. This complex features wonderful shared...
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    33040, Stock Island, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Terrace
    • Shared Outdoor Pool (Unheated)
    • Balcony
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Curry House Room 9 Cozy and compact, this recently renovated attic room in the historic Curry House Bed & Breakfast is perfect for two guests traveling on a budget. This room includes access to the shared backyard pool, air conditioning, and typical home comforts - everything you need for the...
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    33040, Stock Island, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Terrace
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Balcony
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Curry House Room 8 Experience life at the top - the top floor of Curry House Bed & Breakfast, that is! Up to two guests will love staying in this cozy room, which offers a birds-eye view of Key West, access to a shared backyard pool, air conditioning, and more! Curry House sits just three blocks...
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    33040, Stock Island, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
    Cozy, dog-friendly cottage w/ patio - walk to shops, restaurants, and more!1 / 25
    (29)Very good
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Patio
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    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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    33040, Stock Island, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
    Cute, dog-friendly cottage w/ patio - walk to shops, restaurants & nightlife!1 / 30
    (31)Very good
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Patio
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 January 2015
    This rental company is one of the best - I've had numerous occasion to use their services. We arrived very early, but were allowed to park our car at the rental location and...
    Reviewed 17 November 2014
    We had a great stay and will for sure be staying in one of these cottages again. Great location close to nice restaurants approx midway Duval and North 2 blocks. Stayed for a...
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    About this property
    Monroe Suite Enjoy one of the most desirable locations in Key West at this studio-style cottage, where you'll have an outdoor patio, dog-friendly accommodations, and wonderful access to beaches, restaurants, and shops! This cottage which is within walking distance of the vibrant nightlife on...
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    33040, Stock Island, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
    Dog-friendly studio w/ private deck & hot tub - 1 block to Duval St!1 / 39
    (4)Very good
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Hot Tub
    • Air Conditioning
    • Washer
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 August 2014
    We rented three units for 5 nites. We had a great week. The staff was very friendy. Everything was clean, Couldn't have ask for a better place to spend our vacation. Cant wait...
    Reviewed 29 July 2014
    From the minute we stepped off the plane, we were extremely impressed by Key West Vacation Rentals. We flew in on a Saturday morning, and they do not typically do airport...
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    About this property
    Traveler's Palm Spend your Key West vacation days relaxing in your private hot tub and strolling along Duval Street when you stay at this lovely second-floor studio with dog-friendly accommodations. This vacation rental's location is perfect for taking in Key West culture. Located just one...
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    Location Information
    33040, Stock Island, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 4
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Terrace
    • Cable/satellite TV
    • Wi-Fi
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Curry House Room 6 Planning a romantic getaway to Key West? Consider this spacious main-floor suite! Part of the historic Curry House Bed & Breakfast, the suite includes access to a shared pool and home conveniences. Curry House sits in a quiet neighborhood but is just a few blocks away from the...
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    Location Information
    33040, Stock Island, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Balcony
    • Terrace
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Curry House Room 7 The best of Key West is at your fingertips with this charming two-person suite, which includes a shared backyard pool, a semi-private veranda with rooftop views of the city, and typical home conveniences, making it perfect for a traveling couple or a solo adventurer. This room...
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    33040, Stock Island, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Washer
    • Private Garden
    • Air Conditioning
    • Patio
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Louisa's Garden Book this wonderful ground level Old Town cottage with all of the comforts of home and start your vacations off on the right foot! It features an open floor plan with doors that open to back patio to create indoor/outdoor living. Kick back in the living room area and watch your...
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    Location Information
    33040, Stock Island, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Washer
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Borrowed Time *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 simple, modern cottage apartment is an ideal space for a couple or a solo traveler looking to explore the heart of Key West! The...
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    Location Information
    33040, Stock Island, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    Upper-floor suite in historic home w/ shared on-site pool & semi-private veranda1 / 40
    (1)Excellent
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Wi-Fi
    • Balcony
    • Terrace
    • Patio
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 July 2017
    Arrived and all paperwork was ready, easy to communicate thru emails and even phone calls, great customer service. Place was quaint and cute, felt comfortable and safe. Room...
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    Curry House Room 1 If you're planning a romantic Key West vacation for you and your sweetheart, this charming Curry House suite might be just what you're looking for! Up to two guests will enjoy lounging by the shared on-site pool, people-watching on the semi-private veranda, and relaxing in the...
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    33040, Stock Island, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
    Cozy, dog-friendly retreat w/ shared hot tubs, patio, great location in Old Town1 / 29
    (2)Excellent
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    • Hot Tub
    • Grill
    • Patio
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 June 2015
    This place was perfect for our vacation needs. It was close to everything, and the places a bit further away totally doable by renting bikes for the week. We cooked some meals...
    Reviewed 28 August 2014
    This was a last minute booking for us.. we had no idea what type of room we would be getting. Boy were we surprised! The gate is a little hard to find at first and you begin...
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    About this property
    Osprey Suite Take a break from the ordinary with a visit to this tropical hideaway in the heart of Key West's historic district! Ideal for a romantic getaway, this suite promises comfort, space to relax, and a prime location in Old Town. The family dog is also welcome to join you for an additional...
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    Location Information
    33040, Stock Island, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    Studio, 1 Bathroom, Sleeps 2 Quick View
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    Smoking allowed
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    The Galleria - Carey's Corner If you're looking for a budget-friendly home base and plan to spend most of your time enjoying the waves and exploring, this efficient studio is just the ticket. You and one other traveling companion will be in a prime location, within walking distance to the beach and...
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    Location Information
    33040, Stock Island, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
    Tropical Key West studio w/ shared pool - near beaches & Duval St.1 / 25
    (8)Very good
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 September 2015
    Clean, quiet, beautiful garden pool, well managed, prompt shuttle, fun to watch the iguanas marching thru and sun bathing in the palm trees. Locations is great, close to Duval...
    Reviewed 31 July 2014
    Papa's Hideaway is located on a quiet side street, a block away fromKey West's main drag, Duval Street, and a two-block walk from the"Southernmost Point" landmark: a...
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    Papa's Hideaway #4 - Islands in the Stream Plan a romantic getaway for two to Key West at this quaint studio rental complete with a well-equipped kitchenette, furnished patio, and access to a shared swimming pool, well-maintained tropical courtyard, and sundeck. This complex is located in a quiet,...
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    33040, Stock Island, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 4
    Cozy, dog-friendly suite w/ shared hot tubs, patio space, grill, and kitchenette1 / 24
    (3)Average
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    • Hot Tub
    • Patio
    • Air Conditioning
    • Wi-Fi
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 May 2019
    Very nice place to stay in Key West. Super cute little studio with a bed, couch, dinning table & full kitchen. Right across the street from an awesome little local bar...
    Reviewed 28 July 2014
    Located right by the Southernmost Hotel and a block off Duval this was a great stepping off point for fun in Key West. Cuban market on the corner for café con leche each...
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    Heron Suite Heron Suite's hot tubs access, back patio space, and proximity to the beach set the tone for a lovely stay in Key West's historic district! Well-outfitted for a couple's getaway, this suite offers an excellent location paired with the amenities of home. The family dog is also welcome to...
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    33040, Stock Island, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 4
    Cozy tropical suite half a mile from the beach - dog OK1 / 22
    (8)Average
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 February 2017
    Yes, it's located 2-3 blocks South of Duval Street, nearer the Southern-most point end, and it was walkable to everywhere for us, and better on bikes, but I just couldn't get...
    Reviewed 8 October 2014
    The place was pretty decent overall however it is not in the safest feeling part of town. We learned that it is right next to public housing and there are some loud neighbors...
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    The Galleria - Claude Monet Suite This dog-friendly Key West gem offers a palm-covered patio and grill area, a kitchenette, free WiFi, and street parking! Plus, you're walking distance from the beach, historic landmarks, and local dining. Walk a half mile to the beach and enjoy Key West's...
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    Location Information
    33040, Stock Island, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 4
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Grill
    • DVD Player
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Shangri La This home features a 300 sq ft. private deck with a perfect pool and lush vegetation view in a great neighborhood in Key West. This is a second floor unit with wonderful shared space that includes a large pool and grilling area. What's nearby: Bike or walk to the Historic Seaport for...
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    Location Information
    33040, Stock Island, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    Charming, dog-friendly home in a residential neighborhood w/ shared pool1 / 29
    (8)Very good
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Washer
    • Cable/satellite TV
    • Patio
    • Grill
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 April 2016
    We rented the entire compound for our wedding, please see my review on Tropical Village for more information.This is what my (now) husband and I used during our stay.It was...
    Reviewed 3 April 2016
    This place was very private, tropical, had a very nice pool with about 5 or 6 apartment/houses surrounding the pool that you hardly knew were there. They were hidden with...
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    About this property
    Tropical Village - Poolside Paradise If you're looking for the perfect romantic escape for your next getaway, then look no further than this romantic Key West cottage. Featuring room for two guests to enjoy a shared pool and a location that puts you within easy reach of all of the local...
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    Location Information
    33040, Stock Island, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bottoms Up *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 cozy-yet-modern cottage apartment in Key West is a wonderful escape for any party of two! A flatscreen TV in the living room allows...
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    Location Information
    33040, Stock Island, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Galleria - Coral Cove Escape to Key West for a romantic getaway for two and walk to the beach, dining, and other attractions when you make this cozy, efficiency studio yours. You'll be located in a quiet neighborhood and surrounded by tropical vegetation and decking for great views. You'll...
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    Location Information
    33040, Stock Island, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Galleria - Matisse Manor Enjoy the unbeatable location of this Key West studio. A ceiling fan and window unit A/C helps keep the Florida heat at bay, while the covered porches are a great place to enjoy the evenings. What's nearby: This cozy studio apartment is located in a quiet...
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    Location Information
    33040, Stock Island, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Conch Cove *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. Located just a few blocks from the center of Key West, Conch Cove is the ideal spot for your next vacation to the Florida Keys! This...
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    Location Information
    33040, Stock Island, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Cozy, dog-friendly suite w/ shared hot tubs, grill, and patio space to relax1 / 27
    (3)Excellent
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Grill
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    • Patio
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 March 2016
    My Daughter and I stayed in Ibis Suite.We Loved the location and the secluded quietness of our suite.The Cuban coffee shop, the Sandwich shop, the Grocery store, the Trolley...
    Reviewed 2 June 2015
    My friends and I stayed at Ibis this past January (all in our mid 20's). I thought I reviewed this property then, but apparently I did not. It was our first trip to Key West and...
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    About this property
    Ibis Suite Ibis Suite offers visitors a prime location in Old Town Key West, great amenities, and space to relax. Top off your visit with soaking time in one of the property's hot tubs, and you're well on your way to an optimal Key West experience. Here, you're a few blocks off of famous Duval...
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    Location Information
    33040, Stock Island, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 4
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Washer
    • Cable/satellite TV
    • Grill
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Galleria - Salvador's Suite Plan your romantic getaway to this beach condo steps away from Key West's famous beaches, restaurants, and landmarks! The Salvador Dali Suite offers a central location and dog-friendly accommodations. You're situated in the heart of town, so local eateries like...
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    Location Information
    33040, Stock Island, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
    Charming studio w/ shared pool, covered patio - a block from shopping and dining1 / 26
    (8)Very good
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Grill
    • Washer
    • Terrace
    • Cable/satellite TV
    • Balcony
    • Wi-Fi
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 January 2015
    Well, talk about HIGH season. Prices are dear and the lines of cars down the highway get longer each day between Xmas and New Year's. But Key West is a special place, at least...
    Reviewed 23 December 2014
    Stayed for a week before Christmas 2014. I did a bit of research on different properties/hotels, and really wanted to get away from the traditional 'resort' style...
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    Papa's Hideaway #1 - Torrents of Spring Absolutely ideal for a romantic getaway for two, this cozy studio offers a well-equipped kitchenette, a furnished deck, and access to a shared swimming pool at the heart of a beautifully-maintained tropical courtyard. Located just a block from Duval...
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    Location Information
    33040, Stock Island, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 4
    Cozy studio condo w/ shared pool & courtyard - easy beach access! Dogs OK!1 / 27
    (2)Very good
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Terrace
    • Air Conditioning
    • Balcony
    • Cable/satellite TV
    • Patio
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 March 2016
    Loved the stay here. Close to Duvall. Could walk to anywhere on the island including historical sites, any restaurant. Centrally located. Rooms very clean and spacious. Only...
    Reviewed 11 November 2014
    This place was perfect for what we were looking for:Close to Duval, Close to Front Street, Pet Friendly, Shared Space but still alot of privacy. It is a small one bedroom, one...
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    About this property
    Key Lime Cottage Let time wash over you in gentle waves while you relax in the sunny paradise of Key West at this cozy studio condo, offering access to a shared pool, courtyard, and an easy walk to the soft sandy beach. Located in the heart of downtown Key West as part of the larger Banana...
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    Location Information
    33040, Stock Island, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
    Charming tropical getaway w/ shared pool, sundeck, and bar - near Duval Street1 / 29
    (4)Very good
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Balcony
    • Terrace
    • Wi-Fi
    • Cable/satellite TV
    • Grill
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 November 2014
    Papa's Hideaway is a hidden paradise! It is beautiful and comfortable and close to everything. The bed was extremely comfortable and furnished with everything we needed for a...
    Reviewed 19 March 2014
    Loved the location to everything,walking distance and even had parking included in the cost of rental...made me feel relaxed instantly,loved hanging out at the pool and meeting...
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    Papa's Hideaway #2 - The Sun Also Rises This second-floor studio has a private outdoor seating area and plenty of space for up to four guests. Spend time at home splashing in the shared pool or catch some rays on the sundeck. Located in a residential neighborhood, this rental is just a short...
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    Location Information
    33040, Stock Island, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 4
    Cute, dog-friendly condo w/ shared hot tub in the heart of historic Key West!1 / 25
    (2)Very good
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Hot Tub
    • Cable/satellite TV
    • Wi-Fi
    • Grill
    • Air Conditioning
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 August 2014
    The room was a nice size for two friends. It was not fancy, but clean and well equipped. Another plus was the front porch where we sat and people watched while having coffee or...
    Reviewed 26 July 2014
    The Egret Studio is very close to the Southernmost Point and next door to a Cuban cafe, so I had coffee there every morning. The studio is very clean, well appointed and we...
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    About this property
    Egret Suite Settle in at this conveniently located four-person suite, where you'll have access to a shared hot tub and your own kitchenette! Egret Suite can be rented on its own, or as a part of the entire property for larger groups. The family dog is also welcome to join you for an additional...
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    Location Information
    33040, Stock Island, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 4
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • Balcony
    • Terrace
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Creme Brulee Getaway Bask in the glorious waves and sunshine of Key West at this second-floor studio, featuring a shared pool, one private parking spot, and close proximity to the beach, restaurants, and more! This studio is part of Banana's Foster Guest House, which can accommodate a much larger...
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    Location Information
    33040, Stock Island, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
    Spacious room in historic Curry House - shared pool & semi-private front balcony1 / 46
    (1)Excellent
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 May 2016
    Sandy and her team at Curry House are friendly, helpful and welcome you to the B & B with a warm smile and they give you a hug when you leave. I went with my partner and our...
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    About this property
    Curry House Room 4 A fun-filled Key West getaway for two starts with this lovely room in the historic Curry House Bed & Breakfast. Cozy and comfortable, the room includes access to a shared pool as well as a semi-private balcony, which faces the street toward the front of the home. Curry House...
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    Location Information
    33040, Stock Island, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
    Studio condo w/ shared courtyard & pool - walk to everything - dogs welcome!1 / 29
    (1)Very good
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 June 2016
    If you're looking for an affordable place to crash at the end of a few crazy Key West days and nights, this is perfect. Terrific location, right at the intersection of Simonton...
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    About this property
    Sugar Pie Suite Bask in tropical sunshine and waves in the paradise of Key West for your next vacation with this cozy studio. Featuring a kitchenette, shared pool, and courtyard in an awesome central location, two guests will feel right at home here. The family dog is also welcome here for an...
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    Location Information
    33040, Stock Island, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
    Studio, 1 Bathroom, Sleeps 2 Quick View
    Check-in Check-out
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    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Ballyhoo Bungalo * Please note that this home only allows minimum night stays of 28 nights or longer. This adorable, newly-renovated, well-thought-out studio is tiny living at its best! Remove the sofa cushions and open up the comfortable king size Murphy bed, then tuck it away again when not...
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    Location Information
    33040, Stock Island, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
    Studio, 1 Bathroom, Sleeps 2 Quick View
    other traveller has booked this property
    Check-in Check-out
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Honey Bun Hideaway Pack your bags and leave your worries behind for an exciting trip to Key West! This studio has everything you need to have a great time, including access to a shared pool, an outdoor dining area, and nearby beach access for endless sunny days. Part of the larger Banana's...
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    Location Information
    33040, Stock Island, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
    Lovely room in historic bed & breakfast w/ shared pool & a semi-private balcony1 / 43
    (1)Very good
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 February 2016
    Clean, nice neighborhood. Lot's of Florida Key charm. Great location and close to Duvall street and far enough away to enjoy a quiet evening by the pool. Street parking can...
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    About this property
    Curry House Room 3 Get the most out of your vacation days when you book this charming room at the historic Curry House Bed and Breakfast. With room for two and access to a shared pool, this vacation rental is perfect for a quick weekend getaway, a weeklong romantic retreat, and everything in...
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    Location Information
    33040, Stock Island, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
    Studio, 1 Bathroom, Sleeps 2 Quick View
    Check-in Check-out
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    Amenities & Details
    • Washer
    • Air Conditioning
    • Grill
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Galleria - Leonardo da Vinci's Lodge Experience Key West from the comfort of this cozy beach suite, complete with a kitchenette, private bathroom, and sleeping space for two. Your convenient location in the heart of Old Town makes this a wonderful couple's getaway! Walk over to Zachary...
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    Location Information
    33040, Stock Island, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
    Dog-friendly beach suite w/ shared hot tubs, kitchenette, patio space, and more!1 / 29
    (6)Average
    Studio, 1 Bathroom, Sleeps 4 Quick View
    Check-in Check-out
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    Amenities & Details
    • Hot Tub
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 April 2017
    We stayed from Monday through Thursday so we expected lower crowds but were we surprised. Check in was easy but at a different location. It was a surprise to have to park our...
    Reviewed 12 December 2015
    First impression was that room smelled clean. Very secluded and minutes from Duval Street. Second night, noticed a lot of critter activity. Small bugs and roaches. Management...
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    About this property
    Seagull Suite Look no further than this homey suite for your next couple's weekend! Take a dip in the property's shared hot tubs, or simply enjoy the fresh air on the patio space outside your doorstep. Seagull Suite situates you walking distance from historic Duval Street's attractions, from...
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    Location Information
    33040, Stock Island, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 4
    Studio, 1 Bathroom, Sleeps 4 Quick View
    Check-in Check-out
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    Amenities & Details
    • Hot Tub
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Pelican Suite Tucked away in the trees, this Key West hideaway is a great choice for couples or small families. Shared hot tub access and patio space will have you feeling right at home in Pelican Suite! Take a walk a couple blocks down and you're at the beach, toes in the sand. Local staple...
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    Location Information
    33040, Stock Island, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 4
    Studio condo w/ entertainment, full kitchen & private parking - central location1 / 23
    (27)Very good
    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
    33040, Stock Island, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Private Outdoor Pool (Heated)
    • Hot Tub
    • Parking
    • Washer
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Moonlight' is a freshly renovated condo that is located at 1800 Atlantic Blvd on the beach, with sunset views right from your own 28-foot balcony. You'll be able to enjoy quiet afternoons with those balmy Key West breezes wafting through the floor-to-ceiling glass doors. 'Moonlight' is located in...
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    Location Information
    33040, Stock Island, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
    • Balcony
    • Internet Access
    • Parking
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Waterfront
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A beautifully appointed Gulf front Condo in the heart of Truman Annex. Mills place features a walkway flanked by Royal Palms. Mills place was the old military Hospital building. In the mid 80's it was purchased by a developer who renovated the entire property in keeping with the existing...
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    Location Information
    33040, Stock Island, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Grill
    • Parking
    • Shared Outdoor Pool (Unheated)
    • Balcony
    • Air Conditioning
    • Internet Access
    • Washer
    • Sauna
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Caribbean Conch is a fantastic rental with a great location in the 1800 Atlantic Condo Complex. This unit features an extra large floor plan, both bedrooms and the living room have impact resistant sliding glass doors that open on the a large wrap around deck, you may even get a glipse of the...
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    Location Information
    33040, Stock Island, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check-in Check-out
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    Amenities & Details
    • Washer
    • Air Conditioning
    • Sauna
    • Shared Outdoor Pool (Unheated)
    • Parking
    • Internet Access
    • Balcony
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lovely, quiet two bedrom two bath garden-view unit, located very close to the pool. The unit is tiled throughout. Both bedrooms and the living room open on to a beautiful private balcony overlooking the tropical courtyard and gardens. King in the master bedroom,queen in the guest bedroom and two...
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    Location Information
    33040, Stock Island, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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