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Holiday Rentals in Florida Keys, FL

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    Travellers to Florida Keys are booking August dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 30
    5 of 5 stars (5) Excellent
    Marathon
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    1 / 17
    4 of 5 stars (1) Very good
    Key West
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    1 / 11
    5 of 5 stars (3) Excellent
    Marathon
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Hyatt Sunset Harbour Residence Club. 1 week rental 9/25/16 to 10/02/16. Location, Location, Location. 2 bedroom 2 bath. Full kitchen, dining table and living room includes sofa bed. TV's are in bedrooms as well as living room. . Great resort in a great old town location. Unit # is 524. Water... View all property information
    Location Information
    Key West, Florida Keys 33040
    Key West
    1 Bedroom, 2 Bathrooms, Sleeps 6 | Quick View
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    Duval Delight is a breathtaking, newly-renovated 2-story condo located at the historic "Cuban Club" on the "quieter" side of world famous Duval St. This high end vacation rental features a huge 55-inch flatscreen TV in the living room and all brand new furniture including a comfy, pull-out queen... View all property information
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    Key West, Florida Keys 33040
    Key West
    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    Abbey Road - Gated Compound, Sleeps up to 12! Including ;Lennon's Lodge (Sleeps 6 with 8 person hot tub), McCartney's Manor (Sleeps 2 with 2 person hot tub), Starr's Suite (Sleeps 2 with 2 person hot tub) and Harrison's Hideaway (Sleeps 2 with 2 person hot tub) and will accommodate up to 12... View all property information
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    Key West, Florida Keys 33040
    1 / 29
    5 of 5 stars (1) Excellent
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9:15 AM - 5:30 PM daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair... View all property information
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    Key West, Florida Keys 33040
    1 / 29
    Marathon
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    If a scenic vacation is what you're after, this Marathon home is for you. Enjoy beautiful views of the Gulf and nearby Faro Blanco lighthouse, a lovely screened-in terrace, and shared amenities like a pool and hot tub. Now that's a way to experience Florida in style! Set in the Faro Blanco Yacht... View all property information
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    Marathon, Florida Keys 33050
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Sunrise Suites Resort is an island paradise. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped pool surrounded by lush tropical foliage where you can let your cares melt away. Please take a moment to look through our site at our many... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 35
    4.5 of 5 stars (2) Very good
    Key West
    3 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Hibiscus Suite is a queen efficiency with a kitchen, bathroom and a small outdoor deck. Orchid and Jasmine are both one bedroom suites with queen bedrooms, queen sleeper sofas, kitchenettes and outdoor decks. All units have TV/DVD, cable and Free WiFi! This complex offers combined parking for 3... View all property information
    Location Information
    Key West, Florida Keys 33040
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    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** Salt Pond Hideaway is located right off of South Roosevelt Blvd. in the oceanfront Salt Ponds Condominium Complex. It offers a neighborly and relaxing atmosphere with the ocean breezes of the Atlantic right... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 32
    5 of 5 stars (27) Excellent
    Key Largo
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Welcome to Tropical Daze Oceanfront Paradise, located in Ocean Pointe, the finest destination property in the Florida Keys. Our condo unit is right on the ocean, offering spectacular views of the purple and aquamarine waters surrounding Tavernier Key. The condo is gorgeous, extremely well... View all property information
    Location Information
    Key Largo, Florida Keys 33070
    1 / 28
    5 of 5 stars (1) Excellent
    Key West
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Fairwinds at the Foundry is a gorgeous 3 story end unit townhouse in the Foundry section of the Truman Annex. Walking distance to ALL that Key West has to offer! This light and airy end unit is immaculate! Classic and beautiful coastal two bedroom, two and a half bath 3 story townhouse. Enter... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 21
    5 of 5 stars (1) Excellent
    Marathon
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    This spacious three bedroom, two and a half bath Villa will make you feel right at home. Each bedroom has it’s own television, with a 60” flat screen TV in the living room. The Villa has direct sunset views looking out to the Gulf of Mexico, which can be enjoyed from the porch or upper balcony. The... View all property information
    Location Information
    Marathon, Florida Keys 33050
    1 / 24
    5 of 5 stars (6) Excellent
    Marathon
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • x
    About this property
    The casa de munday is a lovely 2300 sq. Ft... 4 bedroom 3 bath deep water canal home located in the middle of marathon mm52. One hour to key largo(mm104) and one hour to key west(mm1)... Ground level with no stairs to climb. The home has plenty of parking for your cars as well as boat trailers. The... View all property information
    Location Information
    Marathon, Florida Keys 33050
    1 / 21
    4.5 of 5 stars (37) Very good
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
    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
    Location Information
    Key West, Florida Keys 33040
    1 / 20
    3 of 5 stars (8) Average
    Key West
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    A Private Tropical Paradise ... is the feeling you get when you enter the pavilion of this award winning villa just a half-block off Duval St. in Old Town Key West. I first visited this private home when it was featured on the prestigious Garden Home Tour of Key West which opens a few select... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 54
    4 of 5 stars (1) Very good
    Key West
    7 Bedrooms, 8 Bathrooms, Sleeps 18 | Quick View
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    About this property
    All together this home has 7 separate bedrooms, each with it’s own bathroom and a ½ bath downstairs in the main house, 2 full kitchens, a BBQ grill and shared courtyard with a plunge pool. The historic downtown property also has 4 off street parking spaces right outside the gated courtyard on... View all property information
    Location Information
    Key West, Florida Keys 33040
    Islamorada
    4 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    • Private Garden
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    • x
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    • x
    About this property
    Tarpon House at Bonefish Bay is one of 12 homes located in Islamorada's premier gated community. Each home features a private pool and hot tub, and guests are welcome to enjoy the common amenities such as beach, tennis court and playground. The house comes with kayak, paddleboard, and bicycles.... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 34
    5 of 5 stars (30) Excellent
    Marathon
    5 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    • Wi-Fi
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    • Ocean Views
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    • x
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    • x
    About this property
    WARNING: DO NOT WIRE MONEY Casa de Lida large estate with 3 separate buildings on almost an acre of land and is directly on the ocean . It is very private, has large sandy beach, a pool, a large dock and phenomenal views. The Kids will enjoy playing in the sand, and the adults will enjoy... View all property information
    Location Information
    Marathon, Florida Keys 33050
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    1 / 20
    Summerland Key
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Step away from the norm and into the most peaceful and quiet blue waters you will ever see, within the Private Island of Serenity, located just 25 miles from Key West and a short boat trip from Summerland Key. This three bedroom home boasts almost 360 degrees of waterfront views from its glass... View all property information
    Location Information
    Summerland Key, Lower Keys
    Summerland Key
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • x
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    About this property
    Canal front, 4 bedrroom, 2 1/2 bath with heated pool and spa 70’ clear dockage (90’ overall) Shore power and water hook up for yachts Jet ski lift Heated pool and spa Minutes to open water – ocean and gulf access 2 Kayaks - with life vests, etc. Pool toys Sleeps 8-10 Over 2,000 square feet... View all property information
    Location Information
    Summerland Key, Lower Keys 33042
    1 / 10
    4.5 of 5 stars (49) Very good
    Key West
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    • x
    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
    Location Information
    Key West, Florida Keys 33040
    Tavernier
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
    About this property
    Stay on a very clean and comfortable 42 ft sail boat in a very quiet and friendly marina in Tavernier, Key Largo.<BR><BR>There is a tikki hut surrounded by gardens. Showers and additional, very clean bathrooms on shore.<BR><BR>Parking is provided. Circle K and gas stations are within walking... View all property information
    Location Information
    Tavernier, Key Largo 33070
    1 / 32
    3 of 5 stars (4) Average
    Key Largo
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Patio
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    • x
    About this property
    Experience the relaxed lifestyle of the Florida Keys. 3 Bedrooms + Loft, 2 Baths, Sleeps up to 8 comfortably. There are 2 large bedrooms on the 3rd floor, each with queen size beds. The first floor bedroom is small with 2 bunk beds. The 4th floor loft is a general purpose room. Newly remodeled,... View all property information
    Location Information
    Key Largo, Florida Keys 33037
    1 / 30
    4.5 of 5 stars (4) Very good
    Key West
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Part of Southernmost Sanctuary Suites People looking for a vacation getaway in Key West are thrilled when they find a hidden gem like The Seagull Suite - located in the gardens of a private compound called The Sanctuary. Location, charm, and island appeal - the Seagull Suite is located in the back... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 21
    5 of 5 stars (3) Excellent
    Key Colony Beach
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    About this property
    New 4 bedroom, 4 Bath duplex. This beautiful new home has a private pool, a dock- 2 10 by 30 decks on the channel. The dock is 37 1/2 ft. There are 2 refrigerators, bait freezer, fish cleaning table, 2 bicycles. All bedrooms have flatscreen TV's. The family room also has a queen sofa bed. 3 of the... View all property information
    Location Information
    Key Colony Beach, Florida Keys 33051
    1 / 23
    4 of 5 stars (32) Very good
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Balcony
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    • x
    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
    Location Information
    Key West, Florida Keys 33040
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
    About this property
    Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9:15 AM - 5:30 PM daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 29
    4 of 5 stars (1) Very good
    Key West
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • ?
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    • x
    About this property
    Part of Conch Republic Cottages "Porchside Paradise" is located in the front section of the "Conch Republic Cottages". This beautiful 'home away from home' features an inviting and spacious front porch - great for people watching - as well as a private two person hot tub. The unit is gated off... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 28
    4 of 5 stars (23) Very good
    Key West
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Lush and tropical gardens surround this beautiful development in the heart of historic Old Town. Private, secured parking beneath the complex and security entrances gives the feeling of exclusivity unparalleled in Key West. The foyer of this Mediterranean Style unit opens to the living room,... View all property information
    Location Information
    Key West, Florida Keys 33040
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9:15 AM - 5:30 PM daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 9
    5 of 5 stars (1) Excellent
    Long Key
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    Local laws prohibit advertising this rental for less than 30 days. There are restrictions for weekly rentals. Enjoy a beautiful solar heated pool with Jacuzzi on the premises. You also will have access to a private homeowner's sandy beach to swim and enjoy sunsets on the next street over. Come to... View all property information
    Location Information
    Long Key, Florida Keys 33036
    1 / 23
    Key Colony Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Welcome to Casa Mar Azul III, an upscale and Luxourious 3 Bedroom, 2 Bath 1/2 Duplex New Home with a private Heated Pool right located in Key Colony Beach. Key Colony Beach is a tropical island paradise, located in the Heart of the Florida Keys, with swaying palm trees and tranquil blue/green... View all property information
    Location Information
    Key Colony Beach, Florida Keys 33051
    1 / 25
    4.5 of 5 stars (20) Very good
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • ?
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    • x
    About this property
    This is the real deal-a light, airy, well-appointed Key West townhome with two stories, two bedrooms, two full baths, and all the amenities needed to enhance your vacation lifestyle. Not to mention a large private deck and an inviting pool for the exclusive use of compound residents. La Prive has... View all property information
    Location Information
    Key West, Florida Keys
    1 / 21
    5 of 5 stars (1) Excellent
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    CONCH WIND - Stop searching, Conch Wind is the property you have been hunting for! This two story Conch Style townhome located in Old Town Key West is nestled in a quiet, secure compound and has everything you have been looking for in a vacation rental home. Plenty of space, beautifully furnished... View all property information
    Location Information
    Key West, Florida Keys 33040
    Marathon
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Please note that this property has a 10AM check-out time. Please note these Check-in Day Requirements for this property: May 21 - Jul 22 : Saturday check-in required, Saturday check-out required.; Jul 23 - Jul 29 : Saturday check-in required, Saturday check-out required.; Jul 30 - Aug 05 :... View all property information
    Location Information
    Marathon, Florida Keys 33050
    1 / 38
    5 of 5 stars (1) Excellent
    Islamorada
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    OSPREY BAY VILLA! Wonderful bayfront home in the heart of Islamorada in the fabulous Florida Keys for rent by the week or monthly. Offering 5 bedrooms and 3 full baths on 2 living levels overlooking the Florida Bay with its incredible sunset views. Sleeps 10 people comfortably. Spacious fully... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 15
    Key West
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    THE MARTHA SUITE Steps from Duval Street, the Lighthouse, the Hemingway Home, shops, restaurants, and galleries! THE TRUMAN SUITES - Four Weekly Vacation Rentals - 3 to 5 Night Minimum Stay Requirement - Lavishly appointed 1 and 2 bedroom suites located ONE HALF BLOCK FROM DUVAL STREET Each... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 35
    Marathon
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • x
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    About this property
    This spacious three bedroom, two and a half bath Villa will make you feel right at home. Each bedroom has it's own television, with a 60" flat screen TV in the living room. The Villa has direct sunset views looking out to the Gulf of Mexico, which can be enjoyed from the porch or upper balcony. The... View all property information
    Location Information
    Marathon, Florida Keys
    1 / 17
    4 of 5 stars (18) Very good
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    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
    Location Information
    Key West, Florida Keys 33040
    1 / 17
    4 of 5 stars (13) Very good
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
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    • x
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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. Bright, tropical colors and tile floors provide an island ambience to... View all property information
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    Key West, Florida Keys 33040
    1 / 31
    5 of 5 stars (4) Excellent
    Key West
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    Book this property at or call our office to avoid unnecessary 3rd party service fees! Alexandria's Secret is a private retreat in the historic district of Key West. With impeccable location and amenities, this three bedroom home is a Key West favorite for its secluded ambiance.This serene... View all property information
    Location Information
    Key West, Florida Keys 33040
    Long Key
    2 Bedrooms, 3 Bathrooms, Sleeps 5 | Quick View
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    • Sauna
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    Ocean view 2 bedrooms 3 baths right across from heated community pool, convenience store and club house. Location Location Location. 50' TV, golf cart available, all high end appliances, furniture, houseware and kitchenware . All you need to bring is your clothes, bathing suit, fishing gear and... View all property information
    Location Information
    Long Key, Florida Keys 33001
    1 / 16
    Key West
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Key West sunsets are famous, and so remarkably spectacular that each-and-every-day of the year, hundreds of people gather at the Mallory Square dock in Key West to celebrate the days end. As the sun slowly 'sinks into the sea', the Key West Sunset Celebration festivities rev up, and every island... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 25
    5 of 5 stars (5) Excellent
    Key West
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • x
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    • x
    About this property
    The name Hermitage invokes the sense of secluded residence or private retreat that aptly describes this inspiring four-bedroom, four-bath home in the heart of Old Town Key West. You'll know the minute you walk through the front door that an artist with considerable flair has decorated Hermitage... View all property information
    Location Information
    Key West, Florida Keys
    1 / 25
    4.5 of 5 stars (9) Very good
    Key West
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
    About this property
    Stay on our fabulous 3 bedroom houseboat and you'll have a vacation that will challenge your imagination! This spacious vacation rental on the water comfortably sleeps up to 8 guests and is completely air-conditioned and heated to keep you comfortable even on the hottest days! Your full kitchen... View all property information
    Location Information
    Key West, Florida Keys 33140
    1 / 26
    3 of 5 stars (2) Average
    Key West
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Part of Conch Republic Cottages Welcome to sweet paradise! Located at 510 Petronia, the 'Orange Blossom Suite' is in close proximity to all the fun-filled action of Duval St, however, it is private enough to not hear any of it! 'Orange Blossom Suite' shares a huge back patio with one other suite... View all property information
    Location Information
    Key West, Florida Keys 33040
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9am - 6pm daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask... View all property information
    Location Information
    Key West, Florida Keys 33040
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Child-friendly
    • x
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    • Smoking allowed
    • x
    About this property
    Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9:15 AM - 5:30 PM daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair... View all property information
    Location Information
    Key West, Florida Keys 33040