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Florida Keys Cottages

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    Travellers to Florida Keys are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    22 Matching Rentals in Florida KeysView all 1,508 rentals
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    Florida Keys Sailing on Conch Key. Bayfront 2 BR cottage with 23 foot Sailboat1 / 19
    (19)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Tropical Cottage with Sandy Beach1 / 12
    (55)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Waterfront Key Largo Bayside Cottage Paradise1 / 20
    (50)Excellent
    2 Bedrooms, 4 Bathrooms, Sleeps 4 Quick View
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    Magnificent Ocean view with 35' dock , Canal home in gated Venture Out Resort1 / 11
    (1)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • Patio
    • Waterfront
    • Grill
    • Washer
    • Central Heating
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful Ocean view, on a canal, three lots from open water in Venture Out Resort; a safe, gated community. Park your boat or kayak right outside your front door on the canal, or just relax and enjoy your mosaic picnic table and 4 patio chairs, and Weber charcoal BBQ. Only 7 steps up or down to...
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    Cudjoe Key, Florida Keys 33042
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Bayfront Cottage, Beach, Dock, Marina1 / 53
    (5)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    • Washer
    • Patio
    • Cable/satellite TV
    • Housekeeping Included
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 November 2018
    Native Floridian, now in Seattle - returned for diving & relaxation in the style of my treasured past. This place was all I had hoped for - screened porch overlooking beach...
    Reviewed 21 February 2018
    A wonderful place to stay. It exceeded our expectations it was very comfortable and well furnished and we especially enjoyed sitting on the screen porch and watching the...
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    About this property
    Our Private Bay Front Key Largo Cottage is our home away from home. Located in Kings Kamp RV park, we have Spectacular Views of Florida Bay as we are 25′ from the waters edge. Our Large Kitchen and Living area are all one with central air conditioning. The 12’x15′ Screened porch with Hammock is...
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    Key Largo, Florida Keys 33037
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 6
    Atlantis House Master Suite1 / 44
    (25)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Housekeeping Included
    • Air Conditioning
    • Patio
    • Hot Tub
    • Parking
    • Wi-Fi
    • Cable/satellite TV
    • Outdoor Dining Area
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 June 2019
    We wanted somewhere special to celebrate our 30th anniversary and did we hit the jackpot! Steve and Kayla are such gracious hosts. The key lime pie that Kayla makes is heavenly...
    Reviewed 25 November 2018
    The Atlantis House and owners Steve and Kayla are wonderful! Located just steps from one of the few beaches on the island and away from Duval Street , the master suite is a...
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    About this property
    About Us... #1 rated Guesthouse in Key West on TripAdvisor for 2016 and 2017! Romantic, Private, Boutique Guesthouse with only 2 suites... 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...
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    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    2 Bedrooms, 1 Bathroom, Sleeps 3 Quick View
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    Amenities & Details
    • Grill
    • DVD Player
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Private outdoor space to enjoy this unique cottage within walking distance of great restaurants and shops. Located in Old Town in a small, quiet compound of cottages sits William's Loft in one of Key West's most desirable neighborhoods. A secluded compound surrounded by lush tropical foliage make...
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    Stock Island, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 3
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Patio
    • Cable/satellite TV
    • Wi-Fi
    • Balcony
    • DVD Player
    • Washer
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Open floor plan 2/2 kitchen, living and dining step right out to deck overlooking canal with a direct view to the bay 45 ft dock master bedroom has a king size bed and guest room has 2 twin beds. Great boating facilities you can dock behind the property and be in the Florida Bay in no time at all...
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    Tavernier, Key Largo 33070
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Grill
    • Wi-Fi
    • Waterfront
    • Air Conditioning
    • Ocean Views
    • Patio
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to paradise! Come experience the amazing Keys and beautiful open water home with ramp and 250 ft. dock for your boat. Consider it a must-see rustic outdoor environment with fishing traps on lot, very typical in the Keys! The private lot is .68 acre with one other rental and still very...
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    Location Information
    Little Torch Key, Lower Keys 33042
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Casa Manana Conch Cottage1 / 41
    (8)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Cable/satellite TV
    • Patio
    • Grill
    • Internet Access
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 April 2012
    We've stayed in 4 different vacation rentals for a month or more at a time, and I think we enjoyed Casa Manana the best. Lots of character, great location, friendly cats and...
    Reviewed 2 July 2011
    The home was wonderful & the perfect size for our family. It was close to everything & we enjoyed the nearby church bells while sitting by the pool. We were surprised...
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    About this property
    Casa Mañana at 800 Virginia Street is perfectly situated for the guest who wants to enjoy Key West at its finest. Located just three blocks from Duval Street, home of world famous watering holes, shopping, and dining, this Old Town jewel is just steps away from Fausto’s Food Palace, Sandy’s Café,...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Washer
    • Parking
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our brand new cottage rental can accommodate up to four guests comfortably. It is located on the Riptide RV Resort. The unit has everything you need to be the perfect 'Home away from home' while you explore the Keys and soak up the sunshine. There is a queen bed in the bedroom, queen size sofa...
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    Location Information
    Key Largo, Florida Keys 33037
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • DVD Player
    • Washer
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in the quiet neighborhood of The Meadows, you’ll find the Conch Republic Retreat, a quintessential cigar maker’s shotgun style house, circa 1890. This 2- bedroom, 2-bath cottage makes a perfect vacation rental for one or two couples who are looking to enjoy all that the island has to...
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    Location Information
    Stock Island, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    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 28 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
    Key West, Florida Keys 33045
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    • Parking
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    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our newly updated studio efficiency unit is part of the motel. It is a studio style room with two queen beds and a queen size sofa sleeper. The room offers a full kitchen with basic features, a table with chairs, flat screen TV with cable and a full bathroom. On Grassy Key, at Mile Marker 59 --...
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    Location Information
    Marathon, Florida Keys 33050
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 6
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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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
    Key West, Florida Keys 33040
    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 28 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
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Grill
    • Washer
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We have (2bed/2bath) with queen bed and two twin beds & pullout couch. Full size indoor/outdoor bathroom newly updated. Rental includes sleeping arrangements for 5 people. A fully equipped kitchen. Jacuzzi to soak in with a cozy terrace overlooking the canal. We provide towels, sheets for the bed....
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    Location Information
    Tavernier, Key Largo 33037
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Ann Street Gardens1 / 125
    (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 1 week ago
    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
    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
    CHARMING KCB POOL COTTAGE, PVT POOL,46 FT DCK,WIFI1 / 106
    (22)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Wi-Fi
    • Cable/satellite TV
    • Washer
    • Air Conditioning
    • Patio
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 days ago
    This was my first time visiting the Keys and it could not have been more perfect! The central location was ideal for our fishing vacation, with a boat dock right at our unit and...
    Reviewed 7 August 2017
    Stayed for a week at Michelle's lovely beach cottage with my husband and 2 sons. The layout of the place is great--even though it is small it is well thought out and everyone...
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    About this property
    $1,500 (Standard Rate for 2019) - additional rates apply to holidays and Lobster Weeks.ASK ABOUT REDUCED FALL RATES! (September 2019- December 21, 2019) Reduced rates do not apply to holiday weeks. PRIVATE-ON-SITE POOL, 45 FT DOCK, PRIVATE BEACH ACCESS AT EXCLUSIVE INCH BEACH- TAGS INCLUDED,...
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    Location Information
    Key Colony Beach, Florida Keys 33051
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    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
    Stock Island, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    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
    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • 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
    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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