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Key West Vacation Rentals

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    Travellers to Key West are booking February dates now. Secure your vacation rental today, and have the perfect trip.
    All 349 Rentals in Key West
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    Casa Manana Conch Cottage1 / 41
    (8)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    A Touch of Bermuda in Key West1 / 19
    (17)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    HISTORIC KEY WEST - Turtle House - Sleeps 61 / 24
    (2)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
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    Pet friendly
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    Smoking allowed
    About this property
    MAR Y Sol is a Beautiful 3 Bedroom Two and a half Bath ocean-front condominium at 1800 Atlantic. Enjoy the balmy breezes from your 60 foot private wrap around balcony with a fabulous view of the Atlantic ocean. Mar Y Sol has renovated kitchen and bathrooms. Mar y Sol is in high demand so during...
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    Key West, Florida Keys 33040
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Balcony
    • Terrace
    • Ocean Views
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    • Central Heating
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Modern 2 bedroom/2 bath condo with nice size balcony overlooks the Atlantic Ocean. California king bed in Master Bedroom and twin beds in the guest bedroom that can be converted into a king bed. Living room sofa with queen sleeper. Nicely decorated with a Key West Flair. Full kitchen with all...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    KeyWestStay.com1 / 17
    (2)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Balcony
    • Internet Access
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    For those of you who want to stay as close to Key West as possible without paying those outrageous Key West prices, stay with us between mile marker 10 and 11 in this waterfront condominium. This small, yet efficient penthouse condominium, 672 sq. ft., stands alone as a roof unit on building 3 of...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Secure Parking
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    Pet friendly
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    Smoking allowed
    About this property
    A great place to stay and play near the water and Old Town Key West! Located in Truman Annex, a secure enclave of historic and exclusive residences, Truman Annex is the most exclusive and magnificent development in Old Town Key West with wide streets lined with multi-million dollar homes that are...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
    • Ocean Views
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    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    HISTORIC KEY WEST -  Cigar House - Sleeps 41 / 20
    (2)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
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    • Porch
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    Pet friendly
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    About this property
    OVERVIEW The Cigar 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 four (4) guests, who are comfortable sharing an open sociable living environment - (1) queen bed, (1) queen...
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    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Patio
    • Housekeeping Included
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    Pet friendly
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    About this property
    About us... #1 rated Guesthouse in Key West on TripAdvisor for 2016 and 2017! Romantic, Private, Boutique.... steps away from the Beach and Ocean and the Key West Marine Park. Free bike use, super fast WI-Fi and off street parking! Reserve 1 room for a couple or both rooms to accommodate up to 4....
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    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    • Waterfront
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    • Private Outdoor Pool (Heated)
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    Pet friendly
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    Smoking allowed
    About this property
    Beautiful 2 bedroom 2 bath unit, with a lovely view of the Atlantic Ocean. This unit is an extra large floor plan with a slighly large balcony. Access the Balcony from both bedrooms and the living room. There is a full size fully equipped eat in Kitchen and a Full size washer dryer. Enjoy all the...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Patio
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    About this property
    This fully furnished turn-key two bedroom bungalow is the perfect spot to escape the winter weather in tropical Key West! Full kitchen, luxury shower, high ceilings and washer/dryer in unit! Also has a nice little fenced in outdoor space with a picnic table for enjoying the beautiful weather in the...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Bimini Key West Penthouse C4241 / 39
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Private Outdoor Pool (Heated)
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    Pet friendly
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    About this property
    Fantastic 1800 Atlantic Penthouse in the highly desirable East building of the facility 2 bedroom 2 bath top floor ocean-view condo at 1800 Atlantic. This unit has been totally renovated and no attention to detail spared, previously owned by the VP of Sony his taste was impeccable. The Master...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    LA DOLCE VITA, OLD TOWN KEY WEST!! STEPS TO DUVAL!! SLEEPS 2-4, 3 BLKS TO BEACH1 / 27
    (6)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Porch
    • Wi-Fi
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Waterfront
    • Balcony
    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    La Dolce Vita is just steps to Duval Street! 'La Dolce Vita' and is a totally renovated condo. Please check out our calendars for availability, photos and video. Everything is brand new from floor to ceilings! 14 foot high ceilings with back lit crown molding in every room for a cozy,...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Ocean Views
    • Terrace
    • Washer
    • Central Heating
    • Patio
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 2 bedroom, fully furnished condominium is located in the Truman Annex, a gated community of private homes and condominiums. Freshly painted and upgraded with custom bedspreads, new key west style furniture, all flat screen televisions, comfortable outdoor furniture, queen bed with two twin...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    LAST MINUTE DISCOUNT! 48' Luxury Yacht and other Yachts Available!1 / 27
    (21)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    Ocean view yacht with beautiful sunsets and sunrises. Underwater windows in the forward cabins makes this yacht unbelievable. Located in the finest most elegant first class marinas giving you full access to its restaurant and private pool during your stay. The marina is located close to...
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    Key West, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 9
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Hot Tub
    • Sauna
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    • Private Outdoor Pool (Heated)
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Fabulous 2 bedroom island view condominium, fully equipped unit. Full kitchen and washer dryer. There is a king in the master bedroom, 2 twins in the guest bedroom and a queen sleeper sofa in the living room. Wireless Internet. The unit is 1357 sq feet. Both bedrooms and the living room have access...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Tropical Escape1 / 26
    (85)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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    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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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Catamaran CALYPSO with Summerallthetime Sailing Co1 / 31
    (12)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    • Ocean Views
    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Beautiful 42' Catamaran Calypso is a spacious Luxury Boat with all the latest Amenities. With 3 Cabins available... it sleeps 6 people comfortably. Each cabin has its own bathroom with all new faucets and electric flush toilets. Aboard Calypso you will find several places to lounge, sit back,...
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    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Private Garden
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    Pet friendly
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    About this property
    Garden Oasis is a first floor condo in the Shipyard Condos in Truman Annex. We are ideally located 2 blocks from the action (restaurants, shops, clubs) of Duval St., and very short walks to sunsets at Mallory Sq, and the beaches of Ft. Zachary Tayler Park. The Shipyard is a lushly landscaped...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Ann Street Gardens1 / 25
    (56)Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Air Conditioning
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
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    About this property
    (Ann Street Gardens is a 16+ compound. Regretfully, no children under 16 allowed.) The cottage is a cozy hideaway. The poolside area is picture-postcard perfect. The location is in the very heart of Key West's Old Town, a half a block off the world-famous Duval Street. In short, Ann Street Gardens...
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    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    LOCATION! Eyebrow Suite-Spacious 1 BR/1BA suite w/ Jacuzzi steps off Duval St.1 / 24
    (4)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Waterfront
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    Pet friendly
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    About this property
    The Eyebrow House is ideally located in a quiet three-unit compound a half block off Duval St. in the heart of Old Town Key West. Our guests enjoy the best of both worlds, as the restaurants, world-class galleries, and vibrant nightlife of Duval St. are just a few steps away. You feel like a local...
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    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
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    Pet friendly
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    About this property
    Come enjoy Island Living at it’s finest, Your own “Little Paradise”. This Two Bedroom Two bath home is nestled on a quiet one way street in The Historic Seaport District. This location is desirable for being walking distance to Duval Street and the proximity to 5 star restaurants, art galleries and...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    • Private Outdoor Pool (Heated)
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    Pet friendly
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    About this property
    Mojitos Island Oasis has Amazing sweeping views of the Atlantic. Watch the sun rise over the Atlantic from the comfort of your King size bed in both bedrooms, access to the private balcony from both bedrooms and living room. Full kitchen. Just a stones throw from the beautiful pool and Jacuzzi. If...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Quilted Giraffe1 / 25
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Patio
    • Grill
    • Private Outdoor Pool (Heated)
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    Pet friendly
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    About this property
    Your space. Your vacation lifestyle. The Quilted Giraffe provides both. This two-bedroom, two full bath home welcomes you from its quiet neighborly front porch facing tree-lined Elizabeth street to its private deck and heated pool in the rear. The location called Solares Hill is a part of Old Town...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
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    • Private Outdoor Pool (Heated)
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    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a unique unit with an amazing view of the Atlantic ocean. Your home away from home, all the conveniences you would need. Both bedrooms and the living room have sliding glass doors that open onto an extensive private balcony with the best view in Key West. You can lie in bed and watch 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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    • Sauna
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    • Shared Outdoor Pool (Unheated)
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    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2 Bedroom Garden-View Condo at 1800 Atlantic Key West with king in the Master bedroom, queen in the guest bedroom and a queen sleeper sofa in the living room. Beautifully renovated custom kitchen in the fall of 2017. Granite counters, Enjoy the many upgrades in this fine unit. Commercial grade...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Spectacular Atlantic Ocean View Condo (MONTHLY)1 / 26
    (19)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    About this property
    ************************************************************************************************************************ NOTE: We are currently accepting only monthly rentals (28 days or longer). Please inquire for a quote....
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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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    Pet friendly
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    About this property
    Top floor penthouse ocean-view condominium at 1800 Atlantic in the highly desirable B building. This unit has recently been renovated and features a new kitchen with granite counters, lovely open floor plan with vaulted ceilings. The elegant master bathroom has a spacious walk in shower. The master...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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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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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Valhalla1 / 25
    (52)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Grill
    • Private Outdoor Pool (Heated)
    • Patio
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    Pet friendly
    Kid friendly
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    About this property
    This two-bedroom, two-bath classic contemporary is the perfect headquarters for your dream vacation. The entire inside is painted cloud white. This choice creates not only a crisp, clean elegance but also serves as the perfect backdrop for an amazing art collection. It's fitting that this special...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, 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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    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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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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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    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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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Banana Key1 / 25
    (5)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Balcony
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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...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Studio, 1 Bathroom, Sleeps 2 Quick View
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    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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    Casa Del Sol, a Key West Vacation (Truman Annex)1 / 26
    (50)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Welcome to Casa Del Sol, a Key West Vacation...your very own luxurious and elegantly appointed 2 bedroom and 2.5 bath townhome with private carport... part of 45 lushly landscaped acres in Truman Annex. As part of President's Walk townhomes in gated Truman Annex, this premier waterfront community...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    The Courtyard1 / 25
    (20)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    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...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    This is a luxury 43 foot yacht. Everything is first class. Full galley. Very clean. Brand new. Great friendly marina. Lots of artists and creative people work and live here. Great restaurant the Hogfish Bar and Grill is right next door. Six beds behind 4 doors and 2 baths. Three AC units....
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    Key West, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
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    1800 Atlantic Condominiums Unit C439 Overlooking Smathers Beach and the Atlantic Ocean, this two bedroom, two bath penthouse condo has just been upgraded including a large, well equipped, open-design kitchen with all new appliances, bamboo cabinets, granite counter tops and an elegant...
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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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    1800 Atlantic Condominiums Unit B117 2 Bedroom Garden-View Condo at 1800 Atlantic Perfect for a family get-away or a group of friends looking to relax in Key West with all the amenities of home. Full size fully equipped eat in Kitchen, Washer/Dryer. Expansive private balcony overlooking the lush...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Admiral's Lane1 / 20
    (21)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    REDUCED JANUARY RATES! As part of the Truman Annex, this stately four-bedroom, three-bath home on Admiral's Lane is tucked away in the beauty and privacy of thick tropical foliage. The Annex neighborhood, named for President Harry Truman who wintered at The Little White House just blocks away, is...
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    Key West, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Beautifully renovated 2 bedroom 2 bath penthouse overlooking the Atlantic Ocean and Smathers Beach. Fabulous kitchen with stainless appliances and granite counter tops. Enjoy the amazing sunrise from the balcony of Awaken to Morning reflections. Recently renovated the master suite has a luxurious...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Rose Treehouse1 / 20
    (6)Very good
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    Classic Key West style defines this two-story Bahamian Colonial tucked away on Rose Lane, which runs only one block in its entirety, from Simonton to Duval. Rose Treehouse is a charming King bed, one-full-bath studio that occupies the whole second floor with balconies off both the front and the...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Ellen's Retreat, Key West, MONTHLY RENTALS ONLY1 / 19
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    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...
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    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Havana Hideaway1 / 75
    (20)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,...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    This newly renovated unit is located just two blocks from world famous Duval Street 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...
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    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    ~ CASABLANCA ~ Gorgeous Cottage w/ Private Pool, Parking, & Tons of Sun!1 / 29
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Casablanca is the perfect get-a-way vacation rental for those seeking a good time, but would like to stay a safe distance from all the Duval Street craziness!! Casablanca is one half of an impeccably maintained duplex that is located on the edge of the Meadows and Historic Old Town. This is a...
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    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Newly remodeled family home with a shared swimming pool and fitness center!1 / 32
    (2)Average
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    About this property
    Let year-round warm breezes transport you to deep relaxation at this three-bedroom, three-bathroom Key West vacation rental. The home's great amenities include a shared pool, a gym, and plenty of space for up to six guests! This home is located on Stock Island, which is between Key West and Boca...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Stunning 2 bedroom ocean-view oasis vacation rental at the fabulous 1800 Atlantic in Key West. Our family owned unit has a new King in the master suite 2 twins in the guest bedroom and a queen sleeper sofa in the living room. The property has a Mexican tile floor in the living area's adding to the...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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