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Holiday Rentals in Key West, FL

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    1 / 13
    4.5 of 5 stars (54) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    4.5 of 5 stars (26) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    4.5 of 5 stars (24) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    4.5 of 5 stars (12) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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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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    €265
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    1 / 25
    5 of 5 stars (10) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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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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    1 / 17
    4 of 5 stars (13) Very good
    Overview Reviews (13)
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    • 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. Bright, tropical colors and tile floors provide an island ambience to... View all property information
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    Overview Reviews (31)
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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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    1 / 12
    3 of 5 stars (1) Average
    Overview Reviews (1)
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    About this property
    Discover paradise of Key West in a distinctive setting. Luxury, two-bedroom, two-bath, (sleeps 4-6) condominium set in a tropical garden with sweeping balconies with views of the Gulf. Your vacation hideaway is decorated in authentic island tradition with fully-equipped modern kitchen, living room,... View all property information
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    1 / 15
    4.5 of 5 stars (26) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    Overview Reviews (26)
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    • Air Conditioning
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    • Dishwasher
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • 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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    1 / 12
    4.5 of 5 stars (60) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    Overview Reviews (60)
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    • 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. Coral Hammock is one of the newest gated communities with 55 luxury... View all property information
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    1 / 21
    4.5 of 5 stars (12) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    Overview Reviews (12)
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    • Air Conditioning
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    • Dishwasher
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    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • 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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    1 / 32
    4.5 of 5 stars (5) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Overview Reviews (5)
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    About this property
    Paradise found reservations must begin and end on a Saturday. You feel it the moment you arrive. It's a rhythm. A rhythm set into motion over a century ago by pirates, artists, writers and other champions of leisure. Today that same rhythm beckons you to discover the charm and grace of Old Key... View all property information
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    €231
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    • Waterfront
    • Water Views
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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
    Want to have a piece of Paradise to call your own? Even tho it for a short stay?…Come have breakfast lunch or dinner in your hidden GEM of a suite overlooking the beach! We are So glad you found us! The Best Stay In Key West! {{{ 5nt Here! $1550 includes tax & cleaning! call if for your date... View all property information
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    Overview Reviews (28)
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    • Air Conditioning
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    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • 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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    From
    €269
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    Overview Reviews (14)
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    • Air Conditioning
    • Balcony
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    • Private Outdoor...
    • Satellite TV
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    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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    €1,808
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    Overview Reviews (8)
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    • Air Conditioning
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    • Washer
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Truman Annex Best Location in Town!! 2 Bedroom 1 Bath ground floor Shipyard Condo. This beautiful townhome sits on a private quiet walking lane and is just a 5 minute walk to downtown where you will find Key West's famous bars and shopping. Also a 10 minute walk to Ft. Zachary Taylor, our... View all property information
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    €204
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    Overview Reviews (2)
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
    About this property
    The 'SeaJay' at La Brisa is located in a gated community overlooking the Atlantic Ocean just steps away from Smathers Beach with it's pristine sand and palm trees. Directly across the street is Key West's longest sidewalk along the beautiful ocean for bike riding, jogging or walking. Smathers... View all property information
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    €231
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    • Air Conditioning
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    • Ocean Views
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
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    • Elder access
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    About this property
    See if this unit is for you! RATE – BOOK – POLICY right here in description. Come have breakfast lunch or dinner in your hidden GEM of a suite overlooking the beach! Please read this ad to expedite Q'S at booking! All rates are base rates unless stated otherwise. Want ocean views? SEE THE... View all property information
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    €278
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    1 / 15
    4.5 of 5 stars (22) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    Overview Reviews (22)
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • 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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    1 / 19
    4 of 5 stars (20) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    Overview Reviews (20)
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • 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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    From
    €198
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    Overview Reviews (1)
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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
    7 day minimum please This fully furnished newly updated getaway is so close to all the local Key West bars & restaurants and museums just take a short stroll or jump on a bike and a way you go... A car is really not necessary in Key west (though parking space for one auto is available) Bike &... View all property information
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    1 / 25
    5 of 5 stars (3) Excellent
    Overview Reviews (3)
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    • Suitable for children
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    About this property
    Great 3rd floor 2 bedroom 2 bath rental unit at 1800 Atlantic. All furnishings replaced in 2011,decorated in an elegant contemporary style. This unit is spacious with a full size fully equipped eat in Kitchen. There is a king bed in the master bedroom, 2 twin beds in the 2nd bedroom and a queen... View all property information
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    €222
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    1 / 24
    4.5 of 5 stars (7) Very good
    Overview Reviews (7)
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Sauna
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    About this property
    Beautifully remodeled, 1374 sq. ft., 2 bedrooms (both are King Beds) 2 Bath condo located on the beach in a resort complex -(SLEEPS 6). Gorgeously landscaped & located RIGHT NEXT TO SMATHERS BEACH, the largest beach in Key West! AMENTIES INCLUDE: Private 40' Balcony, Master suite, Resort... View all property information
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    €333
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    1 / 22
    4.5 of 5 stars (32) Very good
    Overview Reviews (32)
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    • Air Conditioning
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    • Dryer
    • Gym
    • Internet Access
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    About this property
    Fully Appointed Suite- Condominium Unit- 2 Bedrooms, 2.5 Baths (Sleeps 4-5) Our beautifully landscaped property and contemporary housing will provide you with a serene tropical setting ideal for a relaxing vacation getaway. Located off the azure waters of the Atlantic Ocean, minutes away from... View all property information
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    €246
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    Overview Reviews (25)
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    • Sauna
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    • Smoking allowed
    • Suitable for children
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    About this property
    Key West Vacation Rentals 2 Bed 2 Bath Condos On The Ocean with ocean and partial ocean views - rent weekly or nightly. To see both my condos on my website with active availability calendars and virtual tours - Click on my name 'Henry Karp' - just to the right of this paragraph then scroll down... View all property information
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    €184
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    1 / 19
    4.5 of 5 stars (3) Very good
    Overview Reviews (3)
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    • Air Conditioning
    • Balcony
    • Internet Access
    • Satellite TV
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • Elder access
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    About this property
    The Bella Vita is a 1 Bedroom, 1 bath, luxurious, steps from Duval Street. Bella Vita is the sister unit to the La Dolce Vita in the same building, listing 431504. Please check out our for availability, photos and video. Everything is brand new from floor ceilings! 14... View all property information
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    1 / 25
    4.5 of 5 stars (21) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    Overview Reviews (21)
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    • Air Conditioning
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    • Dryer
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    • Shared Outdoor Pool...
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • Elder access
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    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... View all property information
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    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • Elder access
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    About this property
    Two bedroom / 1 bath, second floor, corner unit with front and back porches located at the Shipyard in Old Town, two blocks from Duval Street and everything that's happening in Key West but quiet enough to relax when you need to. Master bedroom has a queen size bed and guest bedroom two twin size... View all property information
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    1 / 15
    4.5 of 5 stars (10) Very good
    Overview Reviews (10)
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Hot Tub
    • Internet Access
    • Private Outdoor...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • Wheelchair access
    • Elder access
    • x
    About this property
    Make our lovely home your dream vacation destination in fun-filled tropical Key West, Florida. '1800 Atlantic' is Key West's premiere luxury condo complex on a private Atlantic Ocean beach. Our beautifully furnished large 2 bedroom and 2 bath condo overlooks a serene tropical garden. Both... View all property information
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    1 / 28
    5 of 5 stars (1) Excellent
    Overview Reviews (1)
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    • Air Conditioning
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    • Dishwasher
    • Dryer
    • Gym
    • Hot Tub
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    My Sunshine Luxury Suite is an upscale property located in Key West, an island paradise. Sunshine Suite provides the luxury and convenience of your own condo home just 90 miles from Havana. Surrounding the resort, you will enjoy lush tropical foliage and amenities such as our tennis court, gym... View all property information
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    1 / 25
    4.5 of 5 stars (15) Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    Overview Reviews (15)
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    • Air Conditioning
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    • Satellite TV
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    • Washer
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    Vacation ever so comfortably in this well-designed one bedroom, one-full-bath courtyard unit at Campbell Court. You can step off your front porch and up to the deck of the enticing, heated, residents-only Monaco pool. Steps to the right, you'll find a raised deck with table, chairs, and shade... View all property information
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    1 / 29
    4 of 5 stars (1) Very good
    Overview Reviews (1)
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • x
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    About this property
    La Dolce Vita is the sister unit to the Bella Vita in the same building, Flip Key listing #333914. Steps from Duval Street! 'La Dolce Vita' is a totally renovated condo. Please check out our calendars for availability, photos and video. Everything is brand new from floor to... View all property information
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • x
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    About this property
    Our unit is a 2 bedroom 2 bathroom condominium with a full kitchen. Located in Key West, FL for Nightly, Weekly, vacation rental. The price of a hotel with the comforts of home. Sunrise Suite Key West is an island paradise. Spend sun-filled days pampered by our warm and friendly staff. Pull up... View all property information
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    1 / 22
    4.5 of 5 stars (3) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    Overview Reviews (3)
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    About this property
    Location combined with history and design makes Coral Condo a prize piece of vacation real estate. This cozy one bedroom is located in the heart of Old Town just one block off Duval Street, where you'll find many of the attractions visitors come to the island to enjoy. This large corner condo is on... View all property information
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    4.5 of 5 stars (11) Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    Having spent a long weekend in this one bedroom, one and a half bath apartment, one previous guest described it as a 'cozy condo hideaway in the heart of historic Key West.' The historic significance is close to home. It starts with the white stucco building that houses this suite and other... View all property information
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    5 of 5 stars (3) Excellent
    Overview Reviews (3)
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Internet Access
    • Satellite TV
    • Washer
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    • Pets allowed
    • Smoking allowed
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    About this property
    Here's Céad Míle Fáilte to friend and to rover That's a greeting that's Irish as Irish can be It means you are welcome a thousand times over Wherever you come from, whosoever you be. Welcome to our home across the pond. We know you will enjoy your time in Key West as much as we do and Our... View all property information
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    5 of 5 stars (3) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    Overview Reviews (3)
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    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... View all property information
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    3 of 5 stars (4) Average
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pets allowed
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    About this property
    Fabulous spacious two bedroom condominiums, directly on the Atlantic Ocean in Key West Florida. The Condo is fully equipped with a full size Kitchen. There is also a full size washer & dryer for your convenience. All rooms have a color cable TV and the unit has high There is an extensive... View all property information
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    5 of 5 stars (1) Excellent
    Overview Reviews (1)
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    • Pets allowed
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    • Suitable for children
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    About this property
    2 bedroom 2 bath top floor ocean-view condo at 1800 Atlantic. This unit has been totally renovated and no attention to detail spared. The Master Bedroom has king bed, The guest bedroom has a queen and the living room has a queen pull-out sleeper sofa. High speed interent available. There is a... View all property information
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    5 of 5 stars (3) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pets allowed
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    About this property
    Unit C232 is one of the premium rental Condo's in the 1800 Atlantic Complex. Beautifully decorated with higher end furnishings. Top of the line full size fully equipped eat in Kitchen. Dining room area and spacious living room. Both Bedrooms and the living room open onto the expansive private... View all property information
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    4.5 of 5 stars (25) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Overview Reviews (25)
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    Everybody knows it's all about location: in this case, a dream vacation location in the heart of Old Town Key West. Duval Street Suite is a two-bedroom, two-full-bath townhouse in a small rooftop community overlooking the island's main artery for fun and entertainment. From your private and... View all property information
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    4 of 5 stars (1) Very good
    Overview Reviews (1)
    Amenities & Details
    • Balcony
    • Dishwasher
    • Grill
    • Hot Tub
    • Internet Access
    • Washer
    • Water Views
    Suitability
    • Pets allowed
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    About this property
    This is a beautiful top floor two bedroom ocean-view unit at 1800 Atlantic. It is an extra large floor plan with expansive views You cannot get a better view than this. There is a full size fully equipped eat in Kitchen. Full size washer & dryer. Both bathrooms were renovated in 2013. The... View all property information
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    • Air Conditioning
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    • Waterfront
    • Wi-Fi
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    • Elder access
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    About this property
    Beautifully Renovated First Floor Studio for Two - Incredible Location in Historic Old Town Gorgeous studio apartment on the first floor of the historic Sailmaker's House. This 28 night minimum vacation rental is located only 1.5 blocks from the Historic Seaport and 4.5 blocks from Duval Street.... View all property information
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    4.5 of 5 stars (2) Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    Overview Reviews (2)
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    • Air Conditioning
    • Dryer
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    • Elder access
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    About this property
    This Peaceful and Cozy Efficiency is the Perfect Place to Rest After an Active Day In Key West! Located in vibrant and diverse Bahama Village, the Vangogh Studio for Two is an economical option for active adult travelers. It is one of the FEW accommodations with a 3 night minimum stay!!! The... View all property information
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    4.5 of 5 stars (20) Very good
    Overview Reviews (20)
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    • Pets allowed
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    About this property
    CALL AND ASK ABOUT OUR WEEKLY SPECIAL WITH 1 NIGHT FREE! You will love staying in this great Key West historic old town location where 90% of the residents are local. They each have an interesting Key West tale to tell and are a very warm,friendly and diverse group. Here you will absorb the... View all property information
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    €181
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    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Sauna
    Suitability
    • Pets allowed
    • Smoking allowed
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    About this property
    2 Bedroom 2 bath Island view condo located in the oceanfront condominium complex with the largest oceanfront pool & 20 person hot tub. Sleeps 4-6. Everything you need for an island vacation without the cramped hotel room! Outdoor balcony access from living and bedroom areas. Fully equipped kitchen.... View all property information
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    4.5 of 5 stars (15) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Overview Reviews (15)
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    • Wheelchair access
    • 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 2 bedroom, 2 bath unit features a huge oceanfront balcony accessed... View all property information
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    €3,246
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    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... View all property information
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