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Condos in Key West, FL

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    297 Vacation Rentals in Key West
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    $2,439
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    1 / 10
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    2 Bedrooms, 5 Bathrooms, Sleeps 4 | Quick View
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    5 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    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... View all property information
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    1 / 18
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Incredible resort during the 'peakest' of peak seasons in Key West, Florida. This extraordinary resort is not right in the heart of the Duval Street area, and it therefore offers the best of both worlds to visitors. Since it's within a short car or cab or scooter or bike ride from the Old Town... View all property information
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    1 / 11
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Tropical oasis in the heart of key west. Historic landmark 1 block from duval street. Walk to the pier for sunset celebrations, artists, musicians and entertainment. Surrounded by restaurants and shops and key wests popular theatre. Mel fishers museum is just down the street. Enjoy bicycles,... View all property information
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    1 / 7
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    This stunning 2 bedroom/2 bath suite can accommodate up to 6 guests. Whether you want the hustle and bustle of Key West or just want to kick back and relax, this resort has it all. View all property information
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    $3,049
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    About this property
    28 NIGHT MINIMUM STAY REQUIREMENT - THE STUDIO AT THE SAILMAKER'S HOUSE Beautifully Renovated Second Floor Studio for Two - Incredible Location in Historic Old Town Gorgeous studio apartment on the second floor of the historic Sailmaker's House. This 28 night minimum vacation rental is located... View all property information
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    $1,829
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    1 / 6
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    Experience a world full of lush and fragrant gardens on a Caribbean Estate tucked away in the heart of Old Town, Key West. Stay in a 2 bedroom unit in a restored historic wrecker's home and wander through the extensive gardens as time transcends you to an era long ago. You can relax and indulge... View all property information
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    1 / 4
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Ocean Views
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    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.... View all property information
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    1 / 6
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Ocean Views
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    About this property
    This Key West condo is legally listed as a one-bedroom. However it could easily accommodate two couples, or a family of 4, with privacy. The first floor includes a full kitchen, full bath, dining area, TV area with a sofa, and a Murphy Bed. The second floor (a lock-out unit) includes a 'closet... View all property information
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    1 / 14
    5 of 5 stars (8) Excellent
    Overview Reviews (8)
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    About this property
    THIS PROPERTY IS A MONTHLY ONLY RENTAL Casa Mañana at 800 Virginia Street is perfectly situated for the discriminating guest who wants to enjoy Key West at its finest. Located just two blocks from Duval Street, home of world famous watering holes, shopping and dining, you are steps away from... View all property information
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    4 of 5 stars (25) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    Overview Reviews (25)
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    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... View all property information
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    $4,756
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    1 / 19
    5 of 5 stars (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 5 | Quick View
    Overview Reviews (1)
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    About this property
    Private home of three bedrooms and 2 1/2 Baths within a gated community. High definition plasma TV found in every bedroom in addition to the living room and high speed internet available throughout. There is access to a large private association pool. This beautiful home is close to ocean and the... View all property information
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    1 / 9
    5 of 5 stars (1) Excellent
    Overview Reviews (1)
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    About this property
    Completely hidden from the street, this recently redecorated garden flat provides you with two private entrances off a large gated manicured garden. Your own private expansive covered bricked front porch spans the width of the garden right out the front door and leads to a beautiful meditation... View all property information
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    $2,134
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    Overview Reviews (55)
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    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. 7 night minimum rental.Paradise is definitely found in this Non-Smoking,... View all property information
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    1 / 8
    4.5 of 5 stars (65) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Overview Reviews (65)
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
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    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. Any reservation obtained under false pretense will be subject to eviction... View all property information
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    $8,476
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    • Suitable for children
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    About this property
    SPRING SPECIALS! 15% off MAY 2015! Please see Specials Page for terms, rules and limitations. To say this townhouse condominium is worth the amassed treasure of Blackbeard, one of the most notorious and wealthy pirates in seafaring history, is a major understatement. The 1950's era art deco... View all property information
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    $3,049
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    About this property
    This vacation home is only licensed for stays of 28 nights or more. Southard Square Hideaway is a newly renovated first floor corner condo perfect for 2 plus space for visiting friends and family! Monthly Rental A surprise awaits you inside the gates of the Southard Square village. Nestled in the... View all property information
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    1 / 10
    4.5 of 5 stars (34) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    Overview Reviews (34)
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    • Air Conditioning
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    • Gym
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    • Pets allowed
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    • Suitable for children
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    About this property
    Roomy condo in the heart of Old Town. Fully equipped kitchen, washer, dryer, microwave, dishwasher, central AC and TV. Large, shared pool. Below are shops, cafes and a health club offering daily memberships. Secured parking for one car. Three blocks to the nearest beach. Families are welcomed... View all property information
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    $7,073
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    1 / 11
    4 of 5 stars (2) Very good
    Overview Reviews (2)
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    About this property
    30 DAY MINIMUM RENTAL Packer Retreat is a beautifully renovated 'Conch' house with many architectural touches in the charming historic district. Designed to bring the outdoors in, this home features a bright living room with cathedral ceilings & tall French doors opening to the pool & garden... View all property information
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    1 / 21
    4.5 of 5 stars (27) Very good
    Overview Reviews (27)
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • ?
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    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... View all property information
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    $15,244
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    1 / 19
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    April Just Became Available/Rare Opportunity...Book NOW! One of the very few & one of the largest oceanfront suites in Key West OCEANFRONT… there is nothing like it. To me, it means being directly on the shoreline with nothing between me and the sensation of the ocean. Totally different from ocean... View all property information
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    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.... View all property information
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    4.5 of 5 stars (37) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    Overview Reviews (37)
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
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    • Elder access
    • ?
    • ?
    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... View all property information
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    4.5 of 5 stars (26) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    Overview Reviews (26)
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    • Pets allowed
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    • Suitable for children
    • x
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    • Elder access
    • ?
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    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... View all property information
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    • x
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    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. The breathtaking view can be seen as soon as you enter the unit. This spacious 2 bedroom unit features a large oceanfront balcony accessed... View all property information
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    • x
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    About this property
    The best of Key West, in the middle of Historic Old Town and a half block from Duval Street and the gates to Bahama Village, a perfect location for visitors to our Island. Guests can stroll to Mallory Square, Fort Zachary Beach or the sunset piers which are all within easy walking distance of this... View all property information
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    $268
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    • x
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    About this property
    Located just a step away from Old Town area surrounded by coconut palms and blooming bougainvilleas this charming one bedroom bungalow is a true island hideaway .The bungalow features an one level open space living/dining area, full kitchen and a spacious bedroom with a king size bed. There is a... View all property information
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    $488
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    • Suitable for children
    • x
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    • Elder access
    • ?
    • ?
    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... View all property information
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    4.5 of 5 stars (37) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    Overview Reviews (37)
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    • x
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    About this property
    Great, popular, quiet townhouse in the well-liked Duval Square complex in the heart of Old Town. One off-street parking space per unit. Easy walking distance to all downtown attractions. Bank, convenience store, health club, hair salon and fine restaurants in the complex. Families are... View all property information
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    • Water Views
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    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
    • ?
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    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. The breathtaking view can be seen as soon as you enter the unit. This is one of the most elegant and colorful 2 bedroom units in the Key... View all property information
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Three story townhouse with master bedroom, deck and full bath on second floor and guest bedroom and full bath on third floor. Kitchen, great room, and half bath on first floor as well as deck and garden. Outdoor grill on deck. Please note that I have a licensed real estate broker in Key West who... View all property information
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    • Smoking allowed
    • Suitable for children
    • x
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    • ?
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    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... View all property information
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    About this property
    Great location, just half a block off Duval Street, walking distance to restaurants, the Atlantic beaches and the Southernmost Point. Casually decorated in soft pine and white, wicker furnishings and sofa sleeper in living room, this four bedroom, three and a half bath home provides a comfortable... View all property information
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    5 of 5 stars (4) Excellent
    Overview Reviews (4)
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    • Air Conditioning
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    About this property
    SEE 'RATES' FOR SPECIAL OFFER OVERVIEW The Conch House is a 100+ year old Cigarmaker's house. The house is recently renovated, charming, spacious, secluded and private. The house can comfortably accommodate a maximum of five (5) guests, who are comfortable sharing an open sociable living... View all property information
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    About this property
    Perfect for two, this Bali-style studio cottage has it all: comfort, privacy and location. 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. Within 2 blocks you'll find Key West... View all property information
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    1 / 23
    4.5 of 5 stars (14) Very good
    Overview Reviews (14)
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    • Air Conditioning
    • Balcony
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    • Satellite TV
    • Shared Outdoor Pool...
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    • Pets allowed
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    About this property
    Two bedrooms, two and a half baths, Foundry Condo 121 Front Street in the Truman Annex, is located in the heart of Key West's Old Town. Fly in and take a taxi from the Key West airport or the Keys Shuttle from the Miami or Ft. Lauderdale airports. One reserved vehicle parking space. Available for... View all property information
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    4 of 5 stars (30) Very good
    Overview Reviews (30)
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    • Air Conditioning
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    About this property
    Thoughtfully restored, Havana Lane, hearkens back to a time when cigar makers lived in the neighborhood, gathering on porch stoops to pass on the latest news. Near the notorious Key West Cemetery this classic conch cottage, embodies the essence of rustic charm while offering modern amenities and... View all property information
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    4.5 of 5 stars (32) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Air Conditioning
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    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    • Elder access
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    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... View all property information
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    4.5 of 5 stars (54) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
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    • Gym
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    • Elder access
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    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. Coral Hammock is one of the newest gated communities with 55 luxury... View all property information
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    4.5 of 5 stars (12) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    • Elder access
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    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. Eaton Manor sits on the north side of LaBrisa and provides easy access to... View all property information
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    1 / 8
    5 of 5 stars (2) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Overview Reviews (2)
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    This beautiful home offers you contemporary luxury combined with exquisite historical charm of Old Town Key West. The open and spacious downstairs floorplan has an abundance of natural light and opens onto a fabulous pool area with an expansive deck. Entertaining your family and friends is... View all property information
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    • Suitable for children
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    About this property
    Our lovely home is rented for a 28 day minimum.Enjoy the lovely Key West ocean breeze from your private Tree House. Two Blocks to Blue Heaven, 4 blocks to the beach, 3 blocks to Duval, 3 blocks to the biggest pool on the Island, you will not find a better or quieter location to enjoy all that Key... View all property information
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    • Smoking allowed
    • Suitable for children
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    About this property
    30 DAY MINIMUM RENTAL Welcome to Casa Alegria! An extended vacation at this Bahamian style conch house is sure to bring you happiness and joy! As you approach the front of the house you'll notice ample off-street parking on either side (a rarity in Old Town!) as well as an easy place to park... View all property information
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    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    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. The breathtaking view can be seen as soon as you enter the unit. The huge oceanfront balcony can be accessed from both the living/dining... View all property information
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    5 of 5 stars (10) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Air Conditioning
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    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Wheelchair access
    • Elder access
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    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,... View all property information
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    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Safe
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
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    About this property
    Three bedroom, four bathroom private home with heated pool stocked with massage water jets and special colored lighting. Breathtaking sunsets can be seen from third floor deck overlooking the Ocean. High definition plasma TV and surround stereo throughout the home. High Speed internet and faxing... View all property information
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