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Key West Vacation Rentals

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$1,000+
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264 rentals in Key West.
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Verandah
2 bedrooms
2 bathrooms
Sleeps 4
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Perfect Pineapple
2 bedrooms
1 bathroom
Sleeps 4
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Emma's Secret
2 bedrooms
1 bathroom
Sleeps 4
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Emma's Escape
2 bedrooms
1 bathroom
Sleeps 4
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Tropical Dreaming
2 bedrooms
2 bathrooms
Sleeps 6
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Crowner's Jewel
2 bedrooms
2 bathrooms
Sleeps 6
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Amelia Home
2 bedrooms
2 bathrooms
Sleeps 6
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A Place In Paradise
2 bedrooms
2 bathrooms
Sleeps 6
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Key West Ginger Whole House
2 bedrooms
2 bathrooms
Sleeps 6
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Linger Longer
2 bedrooms
1 bathroom
Sleeps 5
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Conch Condo
2 bedrooms
2 bathrooms
Sleeps 5
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A Siesta Bay
2 bedrooms
1 bathroom
Sleeps 4
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Parrot Perch
2 bedrooms
2 bathrooms
Sleeps 5
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Shipyard Treasure
2 bedrooms
1 bathroom
Sleeps 4
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Key West Charming
2 bedrooms
1 bathroom
Sleeps 4
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Key West Casa
3 bedrooms
2 bathrooms
Sleeps 6
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Finn Key
2 bedrooms
1 bathroom
Sleeps 4
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Brisa Del Mar
2 bedrooms
2 bathrooms
Sleeps 6
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Beach House Condo
2 bedrooms
2 bathrooms
Sleeps 5
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Papaya Place
2 bedrooms
2 bathrooms
Sleeps 6
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Nautical Dreams
2 bedrooms
2 bathrooms
Sleeps 4
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Artist Garden
2 bedrooms
2 bathrooms
Sleeps 4
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Key West Found
2 bedrooms
2 bathrooms
Sleeps 6
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Lavender Jungle
2 bedrooms
1 bathroom
Sleeps 4
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Duval Sea Turtle
2 bedrooms
2 bathrooms
Sleeps 6
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Duval Breeze
2 bedrooms
2 bathrooms
Sleeps 6
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Ecco Domani
3 bedrooms
2 bathrooms
Sleeps 6
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Key Lime Pie
2 bedrooms
2 bathrooms
Sleeps 4
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Tee by the Sea - Luxury 2/2 1/2 with huge pool, parking and 7 Bikes FREE
2 bedrooms
3 bathrooms
Sleeps 6
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HISTORIC KEY WEST - Main House - Sleeps 8
4 bedrooms
2 bathrooms
Sleeps 8
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HISTORIC KEY WEST - Turtle House - Sleeps 6
2 bedrooms
1 bathroom
Sleeps 6
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HISTORIC KEY WEST - Conch House - Sleeps 5
2 bedrooms
1 bathroom
Sleeps 5
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Alluring Porches
3 bedrooms
3 bathrooms
Sleeps 6
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HISTORIC KEY WEST - Cigar House - Sleeps 4
1 bedroom
1 bathroom
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Paradise Place
1 bedroom
1 bathroom
Sleeps 4
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Sunny View
1 bedroom
2 bathrooms
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Conch Wind
2 bedrooms
2 bathrooms
Sleeps 4
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Osprey
0 bedrooms
1 bathroom
Sleeps 2
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Ibis
1 bedroom
1 bathroom
Sleeps 2
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Seaside Place Key West FL 5 Bedroom House 4 Baths
5 bedrooms
4 bathrooms
Sleeps 12
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2 bedrooms
2 bathrooms
Sleeps 6
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** Totally Renovated Ocean View Condo Great Prices **
2 bedrooms
2 bathrooms
Sleeps 6
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3 other travelers have booked this property
* Book today Anchor drop key west short bike ride from old Town*
2 bedrooms
2 bathrooms
Sleeps 6
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5 other travelers have booked this property
Real World MTV House Key West
10 bedrooms
6 bathrooms
Sleeps 22
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11 other travelers have booked this property
** Steps from Duval 1 Bedroom Townhouse in great complex Hidden secret **
1 bedroom
1 bathroom
Sleeps 4
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2 other travelers have booked this property
Artist Cottage in Truman Annex
2 bedrooms
1 bathroom
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Tropical Escape
2 bedrooms
2 bathrooms
Sleeps 5
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112 other travelers have booked this property
** Fantastic Spring& Summer Stay Downtown walk everywhere **
2 bedrooms
1 bathroom
Sleeps 4
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Easy Livin'
3 bedrooms
4 bathrooms
Sleeps 8
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Atlantis House Master Suite
1 bedroom
1 bathroom
Sleeps 2
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5 other travelers have booked this property
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Key West Vacation Rentals and Condos
Browse through the list of beachfront house rentals in the Florida Keys and you’ll start to feel the warm breeze. You’ll sense the cool sand under your feet and taste the spike of a margarita. Everyone and everything on the island of Key West seems to go at its own pace, which makes it a wondrous vacation destination for families and friends of all ages. House and condo rentals abound – penthouse beach villas on the sandy shoreline, inland cottages in the bustling Old Town district, even fully equipped yachts are available for stay!
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Key West Vacation Rentals and Condos
Browse through the list of beachfront house rentals in the Florida Keys and you’ll start to feel the warm breeze. You’ll sense the cool sand under your feet and taste the spike of a margarita. Everyone and everything on the island of Key West seems to go at its own pace, which makes it a wondrous vacation destination for families and friends of all ages. House and condo rentals abound – penthouse beach villas on the sandy shoreline, inland cottages in the bustling Old Town district, even fully equipped yachts are available for stay!
Where To Rent a Vacation Home in Key West
Vacation rentals in Key West can be found all over town, but knowing what each area offers will help you decide on the perfect place. Condo rentals in Old Town will put you in the center of the action – steps from the famous Duval Street, with numerous restaurants, bars, boutiques, souvenir shops and major attractions. Luxurious, modern house rentals on the beach offer more privacy and relaxation. No matter where you make your home base, if you rent a moped or scooter in Key West, you’ll find it easy to get around without a rental car.
Many House Rentals Near Attractions and Activities For All Ages
Key West vacation rentals scatter the whole island, so you’ll always be close to family fun and adventure. Fury Water Adventures offers jet skis, kayaking, parasailing, boating and some of the best snorkeling and diving excursions you’ll ever find. Fishermen will marvel at the eclectic aquatic life in the crystal-blue waters, while families can take the kids to the Florida Keys Eco-Discovery Center, with interactive and dynamic sea exhibits – all just steps away from the island’s spacious, family-friendly condo rentals. Enjoy the romance of paradise on a sunset dinner cruise to wind down from a busy day on the beach or in town.
Key West Bars and Restaurants
Bustling nightlife and gastronomy surround the house rentals in the Historic Seaport neighborhood. Start your night with frozen daiquiris at the famous Lazy Gecko before moving to the award-winning Italian restaurant La Trattoria on the legendary Duval Street. A visit to Key West wouldn’t be complete without trying the conch fritters. And we recommend you indulge in as many different versions of key lime pie as possible. Parrotheads (you know who you are) should make a beeline to Jimmy Buffet’s Margaritaville Café, where you can order up your very own Cheeseburger in Paradise.
Book a Key West Vacation Rental For Your Next Trip
Vacation rentals in Key West are the perfect way to experience the island like a local. Traipse down Duval Street to take in the culture, enjoy the family-friendly attractions with your children and loved ones and relax on the white-sand beaches with a margarita in hand. Whichever way you vacation, TripAdvisor has the best deals on house rentals, condo rentals, and beach homes in Key West.