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Key West Cottages

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    Travellers to Key West are booking March dates now. Secure your holiday rental today, and have the perfect trip.
    10 Matching Rentals in Key WestView all 300 rentals
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    2 Bedrooms, 1 Bathroom, Sleeps 3 Quick View
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    Atlantis House Master Suite1 / 22
    (25)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Tranquility1 / 24
    (31)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • DVD Player
    • Balcony
    • Cable/satellite TV
    • Terrace
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 June 2017
    Tranquility is a true Key West experience...clean cottage, clean pool, great location! Plan to rent bikes as parking is VERY limited and once you park your car you will not...
    Reviewed 29 June 2015
    The Tranquility Cottage (#5 at The Colony Cottages) is adorable. The cottage is bright, cutely decorated, and the compound is quite inviting. It is conveniently located and an...
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    About this property
    Settled in a small community of Old Town yet only a short walk to Duval Street, this lovely cottage offers everything you can expect from a perfect Key West rental There is a potential deck work scheduled for sometimes in August and part of September which will not affect pool usage The...
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    Location Information
    33040, Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other travellers have booked this property
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    Amenities & Details
    • Patio
    • Housekeeping Included
    • Wi-Fi
    • Private Garden
    • Air Conditioning
    • Parking
    • Cable/satellite TV
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    About us... #1 rated Guesthouse in Key West on TripAdvisor for 2016 and 2017! Romantic, Private, Boutique.... steps away from the Beach and Ocean and the Key West Marine Park. Free bike use, super fast WI-Fi and off street parking! Reserve 1 room for a couple or both rooms to accommodate up to 4....
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    Location Information
    33040, Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Key West Ginger Whole House1 / 23
    (53)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Air Conditioning
    • Cable/satellite TV
    • Grill
    • Parking
    • Wi-Fi
    • Washer
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 August 2019
    We stayed here for three nights, but could have stayed longer. Key West is amazing and this cottage is in the perfect location. We were a bit worried at first as it is next to a...
    Reviewed 29 April 2018
    We stayed here for 10 days in April. Very clean and well stocked with everything you needed. Only a 1/2 block off Duval St. but still very quite. Close to restaurants and...
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    About this property
    Located right around the corner from Banana Cafe and Duval Street ,but still offering plenty of privacy, this cozy cottage with fully fenced yard makes a perfect rental for a small family or few friends trying to make the best of Key West! An absolute jewel of a Key West vacation home a few...
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    Location Information
    33040, Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Ann Street Gardens1 / 25
    (62)Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Patio
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 October 2019
    This is the perfect little spot for two people if you want to be right near all the action. We’ve been to Key West numerous times and stayed all over the island. This was...
    Reviewed 27 October 2018
    I am going back to this one! Historic Hideaways was easy to deal with and very helpful. That's just an extra...this cottage was perfect. There were just 2 of us and the size...
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    About this property
    Ann Street Gardens is a 16+ compound. Regretfully, NO Children under 16 allowed. The cottage is a cozy hideaway. The poolside area is picture-postcard perfect. The location is in the very heart of Key West's Old Town, a half a block off the world-famous Duval Street. In short, Ann Street Gardens...
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    Location Information
    33040, Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Wi-Fi
    • Grill
    • DVD Player
    • Washer
    • Cable/satellite TV
    • Hot Tub
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    As you step through the natural wooden gate onto the brick pathway, you will be embraced by this private garden oasis. Tranquility will overcome you as you pass Buddha, smile at the 'just perfect size' pool and you ring the bronze temple bell each time you enter and channel Hemingway's 'For Whom...
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    Location Information
    33040, Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Air Conditioning
    • Grill
    • Private Garden
    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    As I stand on the front porch of this little Hidden Story-Book Cottage in the Old Town Key West, I could swear I’m in a neighborhood in the Bahamas on Green Turtle Cay. In case you didn’t know, Key West and Green Turtle are ‘sister islands,’ and this quaint neighborhood in the middle of the island,...
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    Location Information
    33040, Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Parking
    • Private Garden
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Key West Cottage located in Mid-town away from the maddening crowd when you want to be and close enough to join in when you're ready. Our cottage is surrounded by lush vegetation including: coconuts trees, mango trees, tamarind trees, banana plants, guava plants, Spanish lime trees and many...
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    Location Information
    33040, Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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