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Key West Apartment Rentals

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    Travellers to Key West are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    191 Matching Rentals in Key WestView all 417 rentals
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    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Key West 2bd/2ba Condo - Monthly1 / 27
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Beautiful, Oversize 2BR/King Beds w/ Large Outdoor Spaces, Location! Truman Annx1 / 15
    (5)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
    • Patio
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    • Porch
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    Pet friendly
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    Smoking allowed
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    The completely renovated Shabby Chicken - come stay with the large and proud newest bird in town!! 5-STAR rating and the best floor plan around. This ground floor, sunny, exceptional, OVERSIZED floor plan with lots more room is only offered in 2 other units in the Truman Annex Shipyard. LARGE &...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    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,...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Sunset Celebration1 / 22
    (1)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Private Outdoor Pool (Heated)
    • Wi-Fi
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    • Balcony
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    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    SUNSET CELEBRATION: 2 bedroom 1 bath Shipyard condo located in Truman Annex. New floors, fresh paint, all new furnishings, artwork, linens and towels. Be one of the first to stay in this totally updated vacation home. Master bedroom has queen bed and guest bedroom 2 twins on either side of the...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Conch in Training1 / 20
    (6)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
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    • Balcony
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    Pet friendly
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    About this property
    The name of this one-bedroom, one full bath condo suggests the most persistent legend of Key West: that vacationers come for a week and stay a lifetime. Located in the prestigious gated Truman Annex community, this unit is the perfect place to try out island living for yourself. From its fabulous...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3 Bedroom Oceanfront Condo Key West1 / 14
    (8)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    • Hot Tub
    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Large 3 Bedroom, 2 Bath OCEANFRONT condo. Breathtaking views of the Atlantic from every room. Tropical landscaped property with large heated pool and Jacuzzi. Just steps to Smathers Beach which has swimming, jet skis, parasailing, etc. Fully appointed condo with all the amenities of home at...
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    Key West, Florida Keys 33040
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Key West Charming1 / 23
    (26)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
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    Pet friendly
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    About this property
    KEY WEST CHARMING at the Shipyard Condominiums condo rental in Key West. This downstairs 2 bedroom 1 bath home has been lovingly cared for by the owners. They actually use the property themselves each spring so they know what will make their guests stay more comfortable. The living and dining...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Seaside Condo DECEMBER SPECIAL $2800 per month1 / 17
    (2)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Outdoor Dining Area
    • Shared Outdoor Pool (Unheated)
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    • Terrace
    • Air Conditioning
    • Secure Parking
    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This delightful sunny, quiet apartment is located across the street from Smathers beach and just a ten minute drive to Old Town. The apartment is set in a large lush tropical garden with two Olympic size swimming tools, tennis court, shuffle board court and outdoor lounging and dining areas, It is...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Treetop Studio w/ Jacuzzi in Old Town, steps off Duval St.1 / 7
    (3)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
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    Pet friendly
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    About this property
    The Treetop Studio 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...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Washer
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    • Balcony
    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Banana Key1 / 25
    (5)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Balcony
    • Terrace
    • Air Conditioning
    • Washer
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    • Cable/satellite TV
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    • DVD Player
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    Pet friendly
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    Smoking allowed
    About this property
    Impressive. Distinctive. Comfortable. The perfect spot for your tropical getaway. This second-story, two-bedroom, two full bath Harbour Place condominium is a part of Key West's prestigious Truman Annex community. From the luxurious pool area one floor below, you can enjoy breathtaking views just...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    We are able to offer reservations in weekly increments with arrivals and departures Fridays, Saturdays, and Sundays only. Overlooking the shimmering span of Gulf of Mexico in historic Old Town, The Galleon Resort puts you in an ideal spot to enjoy the countless charms of Key West. Mingle with...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    About this property
    We are able to offer reservations in weekly increments with arrivals and departures Fridays, Saturdays, and Sundays only. Overlooking the shimmering span of Gulf of Mexico in historic Old Town, The Galleon Resort puts you in an ideal spot to enjoy the countless charms of Key West. Mingle with...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Studio, 1 Bathroom, Sleeps 2 Quick View
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    About this property
    You will love this quiet tree-top studio in the heart of Old Town Key West. Located just a block away from the Historic Light house and Hemingway house and very close to Duval Street. This is a cosy studio ideal for one person or a couple looking for a reasonable Key West get-away. There is...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
    • Washer
    • Air Conditioning
    • Grill
    • Internet Access
    • Sauna
    • Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a lovely 3rd floor partial ocean-view unit. You will love the spacious 50 ft private balcony that runs the length of the unit. The unit is tiled throughout with a full size fully equipped eat in Kitchen. There is also a full size washer dryer for your convenience. Both bedrooms and the...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Housekeeping Included
    • Ocean Views
    • Sauna
    • Waterfront
    • Hot Tub
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    GALLEON RESORT PENTHOUSE with LOFT - 2BR/2BA + GREAT VIEWS OF THE GALLEON MARINA, HISTORIC SEAPORT & OCEAN 5th FLOOR CONDO RENTAL / SLEEPS 8 / 1 Master King - 2 Guest Room Twins - 2 Loft Twins - 1 Queen pullout / EXCEPTIONAL LOCATION, CONVENIENCE & CASUAL LUXURY / On the ocean at the end of...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Shipyard1 / 24
    (25)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Balcony
    • Cable/satellite TV
    • Air Conditioning
    • Secure Parking
    • Wi-Fi
    • DVD Player
    • Washer
    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This cozy two-bedroom, one-bath condo lies hidden behind wrought iron gates and down a winding pathway. The Shipyard, part of the Truman Annex neighborhood named for President Harry Truman, is Old Town's premiere gated waterfront community. The manicured landscaping, verdant palms, and white picket...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Tropical Escape1 / 26
    (84)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Air Conditioning
    • Hot Tub
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This luxurious condo/hotel features a wonderful tropical interior design. It has 2 spacious bedrooms (one room with a king-size bed and a full bath and one queen-size bed with a full bath. The unit has a fully equipped kitchen that looks onto the living room with a queen-size sofa sleeper. The...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Finn Key1 / 24
    (32)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
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    • Private Outdoor Pool (Heated)
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    Pet friendly
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    About this property
    FINN KEY: A beautiful 2 bedroom 1 bath downstairs condo located in The Shipyard section of Truman Annex. This pristine residential community is one of the most requested locations in the heart of Old Town Key West. A wonderful mix of a private community yet easy walking distance to the Duval Street...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Terrace
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    • Patio
    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautifully renovated duplex in Old Town. 2 bed/1.5 bath. Sleeps 4-6. There is a private stairway to apartment/loft upstairs. Upstairs unit is a massive 1100 sq ft with cathedral ceilings and loft (2nd bdrm). There is a king bed in the master, full bed in the loft and a pull-out sofa. Fully...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Vista Fresco : Oceanside condominiums with resort-style amenities1 / 23
    (21)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Balcony
    • Grill
    • DVD Player
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy the resort-style amenities of 1800 Atlantic Condominiums while relaxing in a residential setting amongst neighbors. 1800 Atlantic sits on 400 feet of oceanfront property. An expansive pool and spa sits oceanside surrounded by a lushly landscaped garden of native Key West plants and trees....
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Key West Condo 2 br, 2ba - ocean veiw from balcony1 / 12
    (7)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
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    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The resort all the convenience and comfort of your own home with these spacious fully equipped 2 bedroom condos located just minutes from Smathers Beach and 2 miles from Key West Airport. This location is also two miles from popular Higgs Beach and between 4 miles from the Key West Lighthouse...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
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    • Ocean Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Hyatt Windward Pointe is the most luxurious accommodation in Key West. One king bedroom suite with ocean views, queen bedroom and sleep sofa (accommodates 6), Full kitchen, balcony with ocean views, W/D in unit, TV in every room, large pool and hot tub, volleyball court, amazing landscaping....
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Havana Hideaway1 / 25
    (20)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Air Conditioning
    • Terrace
    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Call it casual luxury. Call it tropical chic. This two bedroom/two full bath Harbour Place condominium is a part of Key West's prestigious Truman Annex community. From the luxurious pool area below, you can enjoy breathtaking views just steps from the Gulf of Mexico. Watch passing tall ships,...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Patio
    • Grill
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    28 DAY MINIMUM Open the door to this brand new home in the very center of Old Town Key West, and begin your perfect extended-stay getaway. Sanctuary on Simonton was newly built in 2015. The paint is barely dry on these exquisite townhomes! Enter through the glass front door and find yourself...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    Henry's Piece Of Paradise On The Ocean In Key West1 / 5
    (34)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Hot Tub
    • Sauna
    • Wi-Fi
    • Air Conditioning
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    • Waterfront
    • DVD Player
    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Key West Vacation Rentals 2 Bed 2 Bath Condo On The Ocean with partial ocean views - rent weekly or nightly. Thirteen-hundred-fifty square feet of fabulous living space located on the second floor with garden and partial ocean views from a 38-foot private balcony accessible from the living and...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
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    • DVD Player
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    • Waterfront
    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a large (1245 SF) 1BR/1BA condo on the 6th floor of the Galleon Resort & Marina.....and is a one of a kind. It features a fantastic, fully equipped kitchen, dining room, living room and a very spacious master bedroom & bath with shower and Jacuzzi tub. This suite will sleep 5, with a king...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 5
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    Enjoy gentle ocean breezes and gorgeous views at Sea Orchid (La Brisa #405E)1 / 14
    (30)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • DVD Player
    • Balcony
    • Cable/satellite TV
    • Grill
    • Private Outdoor Pool (Heated)
    • Internet Access
    • Hot Tub
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    La Brisa beach condominiums offer a Florida charm that is relaxing, easy and captivating. Named for the ocean breezes that flow around the pretty blue and white buildings, La Brisa is an ideal spot to enjoy your Keys vacation. Located on South Roosevelt Boulevard, this secure gated community is...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    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,...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Sundown Refuge1 / 23
    (9)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
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    Pet friendly
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    About this property
    SUNDOWN REFUGE: Balmy breezes, brilliant sunshine and magnificent sunsets await you at Sundown Refuge, located in the exclusive Harbour Place condominium complex in Truman Annex. You'll spend most of your time overlooking Florida Bay in one direction and Truman's Little White House in the other...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    New Beach Club unit - Freshly decorated1 / 29
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Terrace
    • Parking
    • Internet Access
    • Balcony
    • DVD Player
    • Air Conditioning
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Housekeeping Included
    • Hot Tub
    • Ocean Views
    • DVD Player
    • Air Conditioning
    • Waterfront
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The privileges are crystal clear at this breathtaking island resort. Your villa overlooks the Atlantic and our colorful tropical gardens. All come equipped with superior amenities and unmatched Hyatt service. Old Town’s famous galleries and restaurants are just a short distance away. So is the fun...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Pelican Landing Bermuda Retreat1 / 23
    (25)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Shared Outdoor Pool (Unheated)
    • DVD Player
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    • Grill
    • Balcony
    • Cable/satellite TV
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is 25 years old. Everyone in your party must be 25 years old to check in unless accompanied by a parent. Our beautiful waterfront...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    We are able to offer reservations in weekly increments with arrivals and departures Fridays, Saturdays, and Sundays only. Welcome to your own private sanctuary among the lush landscape of Key West - envision old-fashioned screen-enclosed porches, gardens bursting with tropical flowers and crystal...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Parrot Perch1 / 22
    (23)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Cable/satellite TV
    • DVD Player
    • Parking
    • Terrace
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    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    PARROT PERCH -- Located in the gated Shipyard Community in prestigious Truman Annex, this condo in Key West is in a great location and a great value for a great vacation. Parrot Perch is an upstairs 2 bedroom 2 bath condo with a balcony from the living room offering a view of the neighborhood....
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Conch Condo1 / 23
    (11)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Private Outdoor Pool (Heated)
    • Terrace
    • Balcony
    • Parking
    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    CONCH CONDO -- A two-bedroom, two-bath condo in Truman Annex. This second-floor condo features fully equipped kitchen, two full baths, top-quality custom furniture, plasma televisions and home theater in living room, plasma televisions in both bedrooms, soaring cathedral ceilings with ceiling...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Private Outdoor Pool (Heated)
    • Washer
    • Internet Access
    • Waterfront
    • Sauna
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This property has been totally renovated and features a fantastic roll in custom shower which is fully wheelchair accessible, The property has fantastic sunrise views along the Atlantic Coastline and Smathers Beach. 1800 Atlantic boasts an Olympic size heated pool and bubbling Jacuzzi tub. The...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    We are able to offer reservations in weekly increments with arrivals and departures Fridays, Saturdays and Sundays only. Set along the Atlantic Ocean, Hyatt Windward Pointe Resort blends the laid-back Key West style with a modern, upscale resort ambiance. Here is a retreat where you can slow down...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Grill
    • Terrace
    • Parking
    • Balcony
    • Wi-Fi
    • Hot Tub
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ATLANTIC PARADISE -- Imagine the ocean only several yards from your balcony, in a secure gated complex, with all the amenities you could ask for -- pool, Jacuzzi, tennis courts, parking garage with personal parking space. That's what you'll find at Atlantic Paradise. Two spacious king bedrooms,...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Hot Tub
    • Terrace
    • Central Heating
    • Sauna
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Steps to the Beach and Sunrise Nature's boutique offer you an exceptional view of key west's native birds right from your private balcony. It is furnished with all of the comforts of home. Large flat screen tv, ensuite bath, full laundry center, fully stocked kitchen, assigned parking bay and...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Waterfront
    • Cable/satellite TV
    • Parking
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Balcony
    • Internet Access
    • Sauna
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    3 bedroom, 2 bath in private Beachside Resort, yet close to Old Town Key West, just steps to the beach, just a bike ride to all that Key West has to offer. Keys to Paradise will not disappoint. Direct ocean front condo that features 1 master suite with a king size bed, jacuzzi and luxurious walk in...
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    Key West, Florida Keys 33040
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
    • Private Outdoor Pool (Heated)
    • Internet Access
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    • Sauna
    • Balcony
    • Waterfront
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy ocean views from this bright and airy 3rd floor unit. This newly renovated unit comes fully equipped with attention to your every need. King bed in the master and queen bed in the guest room will make your stay comfortable. This unit comes complete with in unit washer/dryer, wireless...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Siesta Bay1 / 24
    (3)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
    • Terrace
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    • Private Outdoor Pool (Heated)
    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    SIESTA BAY -- Beautiful two bedroom one bath upstairs Key West cottage rental in Truman Annex, just steps away from the shared pool and within walking distance of anything you'd want to do in Key West. Bright, airy and with plenty of Key West charm, Siesta Bay will provide you with all the comforts...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Fairwinds: Truman Annex, Parking & Pool, Walk to Shopping Restaurants Beach1 / 28
    (3)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    • Internet Access
    • Cable/satellite TV
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    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Fairwinds at the Foundry is a gorgeous 3 story end unit townhouse in the Foundry section of the Truman Annex. Walking distance to ALL that Key West has to offer! This light and airy end unit is immaculate! The Foundry is a non-smoking community within the Truman Annex. Classic and beautiful...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Balcony
    • Terrace
    • Parking
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    SOUTHARD GETAWAY: Imagine it. Arrive in Key West to a beach-like home in walking distance to all that Key West has to offer. Yes, that's Southard Getaway. Two queen bedrooms upstairs with full bath, open living space downstairs with quiet, shaded deck. Decorated in hues of blue and green that...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Tee by the Sea - NO DAMAGE FROM HURRICANE IRMA , Plus 7 Bikes FREE1 / 30
    (67)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • DVD Player
    • Patio
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    • Wi-Fi
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Very nice luxury 2 bedroom / 2 1/2 bath condo of 1100 sq. ft. less than 1/2 mile outside of Key West in very well maintained gated community, including huge heated pool, clubhouse with fitness center. Sleeps up to 6 with a queen bed in each room and a queen sleeper/sofa in LR. We are 4 miles...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
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    Pet friendly
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    About this property
    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,...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    City Cay1 / 22
    (3)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Balcony
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    • Terrace
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    CITY CAY: Looking for a cozy, quiet spot for just the two of you with all the modern conveniences of home? This lovely Truman Annex Condo is the place! City Cay is our 1-bedroom 1-bath upper level condo that has been lovingly renovated and furnished in a sleek modern style of the most hip urban...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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