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Apartments in Key West, FL

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    Travellers to Key West are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 7
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    1 / 10
    5 of 5 stars (2) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    1 / 20
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    1 / 24
    5 of 5 stars (2) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    THE DOLPHIN HOUSE: Two houses with the comfort of one. The Dolphin House comprises a main house and a guesthouse with pool and outdoor living space comfortably nestled in between. Enter the main house into the spacious, open and airy great room with vaulted ceilings and a wall of French doors that... View all property information
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    Key West, Florida Keys 33040
    1 / 8
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Spacious residential-style 2-bedroom/2-bath villa features private balcony, Master suite with king bed and connecting master bathroom and spa tub; Guest queen bedroom & guest bathroom; Fully equipped kitchen with separate dining ares; Living room with sofa bed; TV/DVD Blu-Ray. Exclusive amenities... View all property information
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    Key West, Florida Keys 33040
    1 / 7
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Unique and beautifully renewed apartment in the heart of Key West. Spacious bedroom with King Size bed and Walk-in Closet, large living room with pull-out sofa bed and kitchen. Take advantage of our unbeatable reopening price and enjoy! If we find that the house has been left excessively dirty,... View all property information
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    Key West, Florida Keys 33040
    1 / 24
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Our Old Town Eyebrow has an ideal location on the island of Key West! Only 1 1/2 blocks from the famous Duval Street but set back in a quiet, comfortable neighborhood for you to enjoy your time with loved ones. Stunning views of the Key West Light house greet you as you enter our home. The unique... View all property information
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    Key West, Florida Keys 33040
    1 / 14
    4.5 of 5 stars (7) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Everything about this historic Key West tropical gem adds up to make a precious private garden cottage. Sitting in the mature tropical tree garden in the hidden back yard, you would never know you're just 1/2 block off Duval Street in Old Town Key West. It is indeed rare to find a cottage property... View all property information
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    Key West, Florida Keys 33040
    1 / 9
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    Steps from the Ocean, Esprit du Vent is a spacious catamaran within minutes of Key West on Stock Island in a yacht club setting with a pool, beach and restaurant. The catamaran has 3 cabins, 1 head, and is bright, airy and spacious. Fully equipped with galley kitchen, oven, stove, coffee maker,... View all property information
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    Key West, Florida Keys 33040
    1 / 17
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    About this property
    Mango Hideaway is ideally located in a quiet three-unit compound a half block off Duval St. in the heart of Old Town Key West. Our guests enjoy the best of both worlds, as the restaurants, world-class galleries, and vibrant nightlife of Duval St. are just a few steps away. You feel like a local as... View all property information
    Location Information
    Key West, Florida Keys 33040
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    1 / 21
    4.5 of 5 stars (35) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    LEEWARD ISLE KEY WEST RETREAT: Small gated compound with only 13 properties, this townhome community is quiet and private right in the heart of Old Town. 2-bedroom 2-bath townhome remodeled from top to bottom. Decorated with Key West flair, this is truly a unique property. Flatscreen TVs, stereo,... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 22
    4.5 of 5 stars (3) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Waterfront
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    The Eyebrow House is ideally located in a quiet three-unit compound a half block off Duval St. in the heart of Old Town Key West. Our guests enjoy the best of both worlds, as the restaurants, world-class galleries, and vibrant nightlife of Duval St. are just a few steps away. You feel like a local... View all property information
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    Key West, Florida Keys 33040
    1 / 25
    4.5 of 5 stars (54) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    AMELIA HOME - 2 bedroom 2.5 bath home with sparkling private pool only four blocks from the Atlantic Ocean and one block from Duval Street entertainment. Kitchen complete with everything to create a gourmet meal. Large open dining and living area. Lush garden with private pool that gives one a... View all property information
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    Key West, Florida Keys 33040
    1 / 28
    4.5 of 5 stars (25) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    LAVENDER JUNGLE: 2 bedroom 1 bath downstairs Shipyard condo located in Truman Annex. Renovated kitchen and upgraded bathroom. Large brick patio and grill. Master bedroom with queen bed and guest bedroom with 2 twins on either side of the full bathroom. Well-equipped kitchen. Truman Annex is a... View all property information
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    Key West, Florida Keys 33040
    1 / 15
    5 of 5 stars (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Private Luxury Home surrounded by lush tropical landscaping. The fusion of a mid-century Florida home with dramatic Caribbean design, has created an ideal contemporary "Floribbean" style villa in the Casa Marina district of Key West. Walking distance to all Old Town has to offer, as well as a... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 13
    4.5 of 5 stars (5) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Looking for the perfect Key West get away or corporate retreat? Look no further, here is your opportunity. This little gem is located one block from the world famous Duval Street. This stunning second floor, one bedroom one bath condominium is filled with quality, style and class throughout. The... View all property information
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    Key West, Florida Keys 33040
    1 / 24
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    A great place to stay and play near the water and Old Town Key West! Located in Truman Annex, a secure enclave of historic and exclusive residences, Truman Annex is the most exclusive and magnificent development in Old Town Key West with wide streets lined with multi-million dollar homes that are... View all property information
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    Key West, Florida Keys 33040
    1 / 22
    4 of 5 stars (45) Very good
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    OSPREY COTTAGE: This cozy cottage is located in The Colony Suites, a tropical compound nestled in the heart of Old Town Key West. Osprey offers all the amenities for two who want a larger space than a hotel room but appreciate the amenities of a vacation rental. Sunny and bright this cottage has... View all property information
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    Key West, Florida Keys 33040
    1 / 9
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    ***CHECK IN DATES FOR THIS RESORT ARE FRI/SAT/SUN. RATES ARE SUBJECT TO CHANGE UNTIL RESERVATION IS CONFIRMED*** Situated on the Atlantic Ocean, the property captures Key West style with modern convenience. Conveniently located near Key West Int'l airport and only a short distance to beaches,... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 23
    5 of 5 stars (10) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Balcony
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    ISLAND WIND: When balmy breezes beckon and tropical retreats call your name, Island Wind will be just the escape you need. Located in the pristine gated community of Windward Park this 2 bedroom, 2 bath Bahamian-style townhome is surrounded by lush landscaping and views of a sparkling swimming... View all property information
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    Key West, Florida Keys 33040
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    1 / 18
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Unique and beautifully renewed apartment in the heart of Key West. Spacious bedroom with King Size bed and Walk-in Closet, large living room with pull-out sofa bed and kitchen. Take advantage of our unbeatable reopening price and enjoy! If we find that the house has been left excessively dirty,... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 27
    4 of 5 stars (11) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    TRUMAN'S HIDEAWAY: Lovely condo in the exclusive Harbour Place condominium complex in Truman Annex. Spacious living/dining room area, fully equipped kitchen, Master bedroom with king bed, guest bedroom with bunk bed (1 twin on top, 1 full on the bottom, 1 twin trundle on the bottom) private deck... View all property information
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    Key West, Florida Keys 33040
    1 / 27
    5 of 5 stars (52) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    SHIPYARD TREASURE: 2 bedroom 1 bath Shipyard condo has it all. Located in Truman Annex, there is a shared pool, off street parking and 24 hour security. Shipyard Treasure is a 2nd floor condo with private full-length balconies front and rear. This property has an open and airy feeling and is one... View all property information
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    Key West, Florida Keys 33040
    1 / 25
    5 of 5 stars (44) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • ?
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    • x
    About this property
    Poinciana House, a one-bedroom, two-full bath conch cottage, is a standout in authentic Florida design and guest friendliness. The private pool area and tropical garden is where you find the namesake Royal Poinciana tree complete with a chair hammock beckoning from one enormous branch. Swinging... View all property information
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    Key West, Florida Keys
    1 / 28
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    * This vacation home is available to rent on a monthly basis only * Dating all the way back to 1884, this delightful 3BR home is located in Bahama Village, part of Key West's prominent Old Town neighborhood. This single-family home is available to rent on a monthly basis. If you'd like more... View all property information
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    Key West, Florida Keys 33040
    1 / 63
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Allinclusivecharter provides the perfect getaway on your own private crewed luxury motor yacht in the Florida Keys area. Being the only guests on our board, you are treated like royalty. Do what you really want, when you want. Your voyage is personalized and is a customized vacation tailored to you... View all property information
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    Key West, Florida Keys 33040
    1 / 15
    4.5 of 5 stars (47) Very good
    1 Bedroom, 2 Bathrooms, Sleeps 2 | Quick View
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    • x
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    Tucked away in an inviting compound you'll find the perfect hideaway called Ann Street Cottage; a charming one bedroom cottage. The quiet compound is located just one block from Duval Street combining the best of both worlds for relaxing and taking advantage of all that Key West has to offer.... View all property information
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    Key West, Florida Keys 33040
    1 / 27
    5 of 5 stars (2) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    CITY CAY: City Cay is our 1-bedroom 1-bath upstairs condo in Truman Annex that has been lovingly renovated and furnished in a sleek modern style. Stay connected in the living room with high-end electronics including HDTV, WIFI and an over-the-top stereo system. Relax on the covered back balcony... View all property information
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    Key West, Florida Keys 33040
    1 / 24
    5 of 5 stars (9) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    SUNDOWN REFUGE: Brilliant sunshine and magnificent sunsets in the Harbour Place condo complex in Truman Annex. Overlook Florida Bay in one direction and Truman's Little White House in the other direction from the privacy of deck. Fully furnished with the necessities of home and anything you'll... View all property information
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    Key West, Florida Keys 33040
    1 / 21
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
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    About this property
    CONCH WIND - Stop searching, Conch Wind is the property you have been hunting for! This two story Conch Style townhome located in Old Town Key West is nestled in a quiet, secure compound and has everything you have been looking for in a vacation rental home. Plenty of space, beautifully furnished... View all property information
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    Key West, Florida Keys 33040
    1 / 29
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
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    • x
    About this property
    Unique oceanfront living only 65 feet from the Atlantic! The Key West Beach Club is a quiet, peaceful residential building that sits directly on the water as few do in Key West. The breathtaking view can be seen as soon as you enter this spacious 2 bedroom condo. It has just been purchased and... View all property information
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    Key West, Florida Keys 33040
    1 / 9
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
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    About this property
    President’s Walk is perfectly located in the Truman Annex. A quick stroll to Duval Street and minutes from Fort Zachary Taylor State Park and its beach, this gated community offers lush gardens and a beautiful community pool at your doorstep. For Key West history buffs, Truman's Little White House... View all property information
    Location Information
    Key West, Florida Keys
    1 / 20
    3 of 5 stars (1) Average
    Studio, 1 Bathroom, Sleeps 3 | Quick View
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    This studio has been newly remodeled with no expense spared. Free street parking in front of property and plenty more spots in very close vicinity. This guest room is cozy (the size of a small hotel room, 10'X12.5') with a QUEEN size bed but is so much better than a hotel room. We provide high... View all property information
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    Key West, Florida Keys 33040
    1 / 9
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    1 bedroom with king bed. Living room with pull out sofa bed. 1 bath with jacuzzi tub and shower. Washer and dryer in unit. Balconies off of bedroom and living room with marina view. Stainless steel appliances. The Galleon has a heated pool with hot tub. A small private beach. Poolside tiki bar... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 19
    4.5 of 5 stars (36) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    CONCH WIND: Conch-style townhome in Old Town Key West nestled in a quiet, secure compound. Open floor plan with spacious living room and dining area with an open kitchen. A separate private deck just off the dining area complete with laundry closet. Guest bedroom on the main level with 2 twin beds... View all property information
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    Key West, Florida Keys 33040
    1 / 28
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    SUNSET CELEBRATION: Coming Soon! 2 bedroom 1 bath Shipyard condo located in Truman Annex. Currently undergoing renovation to include new floors, fresh paint, all new furnishings, artwork, linens and towels. Be the first to stay in this totally updated vacation home. Master bedroom will have queen... View all property information
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    Key West, Florida Keys 33040
    1 / 23
    4.5 of 5 stars (32) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    FINN KEY: 2 bedroom 1 bath downstairs condo in The Shipyard section of Truman Annex, one of the most popular spots in Old Town Key West. Remodeled with attention to detail, the kitchen sparkles with top of the line appliances, cabinetry and every amenity needed. Opens to a sunny living room... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 39
    5 of 5 stars (35) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    May Special $299 a night. This Luxury unit is 1375 sq ft of breath taking beachfront living space in this tropical complex. Great views from the 40 foot deck which encompasses the whole unit. Every room has a spectacular view of the tropical Nature Preserve and the Atlantic Ocean. The complex is... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 24
    4.5 of 5 stars (56) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Shared Outdoor Pool...
    • DVD Player
    • Balcony
    • Internet Access
    • Satellite TV
    • Parking
    • Terrace
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    • Pet-friendly
    • Child-friendly
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    • Smoking allowed
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    About this property
    DUVAL BREEZE: 2 bedroom 2.5 bath townhome in Duval Square. 1st floor offers an open floor plan with a well stocked kitchen, spacious living room, dining room, half bath and French doors to your own private balcony. 2nd floor has 2 bedrooms with bath ensuite. Master bedroom has a private balcony.... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 20
    4.5 of 5 stars (47) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Terrace
    • Parking
    • Balcony
    • DVD Player
    • Shared Outdoor Pool...
    • Satellite TV
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    DUVAL SEA TURTLE: This townhome has 2 bedrooms and 2.5 baths with a balcony off the master bedroom and the living room. Covered, gated parking space, WIFI, 3 TVs, free long distance calls King mattress, washer/dryer, and living room furniture new in March 2014. There is a community pool area to... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 22
    4.5 of 5 stars (16) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Wi-Fi
    • Washer
    • Satellite TV
    • Private Outdoor...
    • Parking
    • Grill
    • DVD Player
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    The Pineapple Cottage is tucked away and totally private, yet it is only a half a block from Duval Street. This two story "cottage" offers a first floor bedroom that opens through french doors to the private pool and gardens. A second floor suite includes a bedroom and bath plus a seperate living... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 17
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Satellite TV
    • Air Conditioning
    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • x
    About this property
    Island living is made easy in this tropical one bedroom, 2-story Key West cottage. A classic-contemporary Key West style, this attractive rental home is designed with a graceful spiral stair case that connects the 1st and 2nd floors and a romantic gingerbread Juliet-style 2nd floor balcony... View all property information
    Location Information
    Key West, Florida Keys
    1 / 33
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • DVD Player
    • Air Conditioning
    • Satellite TV
    • Private Outdoor...
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Located on a quiet street in the Meadows of Key West; a tranquil residential neighborhood located just behind the Key West Historical district. This home offers you a two bedroom one bathroom main house with a separate one bedroom cottage with a full bathroom. The private pool and outdoor deck area... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 29
    4.5 of 5 stars (26) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Satellite TV
    • Private Outdoor...
    • Internet Access
    • Parking
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    KEY WEST CHARMING: Downstairs 2 bedroom 1 bath home in Truman Annex, a secluded gated community in Old Town Key West. Living/dining area opens to the large back deck that is one of the best spots on the island to relax. Master bedroom has queen bed; 2nd bedroom has 2 twins. Well-equipped kitchen... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 21
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Air Conditioning
    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Everyone dreams of a charming Key West cottage, tucked away in a tropical sun garden where flowers and trees flourish around an outdoor living porch all year round. This private cottage has all of that and more. Situated in the Conch Grove Garden compound, in Old Town Key West, this quiet little... View all property information
    Location Information
    Key West, Florida Keys
    1 / 6
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Waterfront
    • Satellite TV
    • Patio
    • Washer
    • Hot Tub
    • Air Conditioning
    • Internet Access
    • Ocean Views
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • ?
    About this property
    This 1200 sq ft luxury apartment in the the heart of Old Key West is located only 2 blocks off Duval St and is a short walk or bike to all the fun of Key West ! Very quiet street with no through traffic. The property is completely private and safe, surrounded by a 6 foot gated fence and tropical... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 20
    4.5 of 5 stars (50) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Parking
    • Hot Tub
    • Grill
    • Satellite TV
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    KEY WEST GINGER HOUSE: This historic home was built in 1933 and is the very image of a traditional conch cottage. The Key West Ginger House takes advantage of every breeze with plenty of windows and French doors keeping the home light and airy. High ceilings and wood floors flow throughout .... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 38
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Hot Tub
    • Terrace
    • Balcony
    • Patio
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    28 DAY MINIMUM STAY, PLEASE DO NOT SEND REQUESTS FOR SHORTER PERIODS! Enjoy the amenities of a luxury hotel in the privacy of our home for a fraction of the cost. Located on the sunset side of Shark Key island, a 10 minute drive from Key West. With 2800 sq. ft., three bedrooms, three and a half... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 26
    5 of 5 stars (2) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Balcony
    • Grill
    • Private Outdoor...
    • Internet Access
    • DVD Player
    • Satellite TV
    • Terrace
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    BLOOM'N PARADISE: Private residence with 3 bedrooms and 3 bathrooms in the main house plus a pool house with 1 bedroom 1 bath in Truman Annex, a prestigious gated community in Old Town. Surrounded by tropical greenery in a beautiful quiet gated community 2 blocks from Duval Street and Mallory... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 14
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Amenities & Details
    • Washer
    • Internet Access
    • DVD Player
    • Patio
    • Satellite TV
    • Porch
    • Air Conditioning
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    This is a brand new listing to VHR! We are running a JUNE SPECIAL DISCOUNT!! The Rooster Retreat along with my attention to detail and welcoming our guest has earned over 30 5-STAR ratings (Listed with another vacation site). Come stay at the Rooster Retreat for your own retreat - it is a... View all property information
    Location Information
    Key West, Florida Keys 33040