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Key West Vacation Rentals

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    $410 Average
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    Travellers to Key West are booking January dates now. Secure your vacation rental today, and have the perfect trip.
    All 416 Rentals in Key West
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    Best Old Town Location in Key West1 / 17
    (17)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Penthouse On Duval ~ Weekly Rental1 / 20
    (10)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Patio
    • Private Outdoor Pool (Heated)
    • Grill
    • Cable/satellite TV
    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Perfect for two families wanting to vacation together or large groups. This is a large duplex home with a total of 5 bdrms and 3.5 bathrooms: One side has 3 bdrms (two rooms with queen, one room with 2 twins) + 2 baths. The other side has 2 bdrms (one room with queen, one room with 2 twins) + 1.5...
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    Key West, Florida Keys 33040
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Terrace
    • Balcony
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Key West is like a little piece of the Caribbean at the lowermost point of the United States: it’s reliably warm, the waters are a gorgeous turquoise, and it is a small, intimate community. From this second floor condo it’s just a short walk to Mallory Square’s sunset celebrations, the Ernest...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    New Beach Club unit - Freshly decorated1 / 29
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Terrace
    • Parking
    • Internet Access
    • Balcony
    • DVD Player
    • Air Conditioning
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Unique oceanfront living only 65 feet from the Atlantic! The Key West Beach Club is a quiet, peaceful residential building that sits directly on the water as few do in Key West. The breathtaking view can be seen as soon as you enter this spacious 2 bedroom condo. It has just been purchased and...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Parking
    • Private Garden
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Key West Cottage located in Mid-town away from the maddening crowd when you want to be and close enough to join in when you're ready. Our cottage is surrounded by lush vegetation including: coconuts trees, mango trees, tamarind trees, banana plants, guava plants, Spanish lime trees and many...
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    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Pelican Landing St.Croix Penthouse - Condo with a Shared Pool1 / 30
    (39)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Terrace
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Internet Access
    • Grill
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is 25 years old. Everyone in your party must be 25 years old to check in unless accompanied by a parent. Our beautiful waterfront...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    2 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Washer
    • Grill
    • Wi-Fi
    • Air Conditioning
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spacious, tranquil Old Town Key West home. Two bedrooms, 2.5 bathrooms, sleeps up to 7. NOTE: On this page, TripAdvisor might be showing the summer price. The price changes seasonally. We are booking **monthly** renters for September, 2017. Also looking for 30-day renters starting April 15,...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Just half a block from Duval and one block from the Ernest Hemingway House! Stay in the heart of all the action with this fully renovated apartment. Enjoy the Key West experience with all the comforts of home. Walk to restaurants, bars and all the tourist attractions while still being able to relax...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Grill
    • Washer
    • Patio
    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This genuine Key West combo of our Private Pool Garden Villa plus a classy private studio cottage that adjoins the property next door, can be your very own get-away for a week or more. When rented together, we call the property the Lazy Iguana, and it's available to rent together from May 2016...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Terrace
    • Air Conditioning
    • Parking
    • Balcony
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    MONTHLY RENTAL- 28 DAY MINIMUM Duval Square Delight is located in a quaint town home community just steps from Duval Street. Upstairs there are residential units and a rooftop pool, while downstairs there are shops and restaurants surrounded by cobblestones and mature, tropical landscaping. Duval...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Key West Harbour Oceanfront Suites #11 / 25
    (53)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    • Parking
    • Internet Access
    • Sauna
    • Washer
    • Waterfront
    • Balcony
    • Terrace
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 5
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • Patio
    • Grill
    • Washer
    • DVD Player
    • Internet Access
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Make this cozy and chic Key West cottage your home away from home for your next Florida vacation, and revel in a private pool, deck, and covered back porch, as well as close proximity to the beach. And the real bonus: you can bring your favorite canine friend along, too. You'll be situated only six...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • DVD Player
    • Patio
    • Cable/satellite TV
    • Wi-Fi
    • Grill
    • Washer
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    On an island full of resplendent Victorian architecture, the trend toward minimalist design has made its mark. This 2-story tropical luxury home is a ubiquitous example of this, an ingenious melding of classic Old Town Key West architecture with contemporary pared-down design. Created by connecting...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    Seaport Treasure Estate ~ Monthly Rental1 / 102
    (1)Excellent
    6 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Air Conditioning
    • Patio
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Washer
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    While you won’t need a treasure map to find this exclusive resort-style estate, you’ll know you’ve discovered a rare island gem from the moment you walk through the private gates. Hidden by white picket fences and mature tropical landscaping, this spacious Seaport Treasure Estate is cleverly...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 12
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