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Key West Vacation Rentals

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$1,000+
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245 rentals in Key West.
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Seaside Place Key West FL 5 Bedroom House 4 Baths
5 bedrooms
4 bathrooms
Sleeps 12
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Sunrise at Seaside Condo 2 Bedroom
2 bedrooms
2 bathrooms
Sleeps 5
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209 other travelers have booked this property
Tropical Escape
2 bedrooms
2 bathrooms
Sleeps 5
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112 other travelers have booked this property
Sunrise Suite Key West 2 Bed Rooms 2 Full Baths
2 bedrooms
2 bathrooms
Sleeps 6
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97 other travelers have booked this property
Oceanfront 2 Bedroom 2 Bath Condo Key West Florida
2 bedrooms
2 bathrooms
Sleeps 6
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29 other travelers have booked this property
'Oceanside Oasis' * Kings Pointe: Direct Ocean Views & 3 BR'S
3 bedrooms
2 bathrooms
Sleeps 6
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Artist Cottage in Truman Annex
2 bedrooms
1 bathroom
Sleeps 4
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Henry's Piece Of Paradise On The Ocean In Key West
2 bedrooms
2 bathrooms
Sleeps 5
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Ambrosia - OLD TOWN/HISTORIC SEAPORT, large POOL, wrap around porch, washer/dry
1 bedroom
1 bathroom
Sleeps 4
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Conch Haven Old Town 1/1 MONTHLY Rental
1 bedroom
1 bathroom
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13 other travelers have booked this property
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The Green House - Garden
1 bedroom
1 bathroom
Sleeps 4
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2 other travelers have booked this property
Brisa Del Mar
2 bedrooms
2 bathrooms
Sleeps 6
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Key West Casa
3 bedrooms
2 bathrooms
Sleeps 6
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Real World MTV House Key West
10 bedrooms
6 bathrooms
Sleeps 22
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11 other travelers have booked this property
Duval Sea Turtle
2 bedrooms
2 bathrooms
Sleeps 6
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Osprey
0 bedrooms
1 bathroom
Sleeps 2
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Casa Del Sol, a Key West Vacation (Truman Annex)
2 bedrooms
3 bathrooms
Sleeps 6
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49 other travelers have booked this property
Papaya Place
2 bedrooms
2 bathrooms
Sleeps 6
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Casa Grande
5 bedrooms
5 bathrooms
Sleeps 12
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Alluring Porches
3 bedrooms
3 bathrooms
Sleeps 6
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Amelia Home
2 bedrooms
2 bathrooms
Sleeps 6
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Key West Charming
2 bedrooms
1 bathroom
Sleeps 4
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Sunshine Daydream: Private Home 1/2 Block Off Duval in Gallery District -
2 bedrooms
3 bathrooms
Sleeps 4
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2 bedroom Condo Presented Key West Style
2 bedrooms
2 bathrooms
Sleeps 5
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232 other travelers have booked this property
Linger Longer
2 bedrooms
1 bathroom
Sleeps 5
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'LOST SHAKER OF SALT' ~ 3 Bed, 2 Bath Pet Friendly Home with 40' Private Pool
3 bedrooms
2 bathrooms
Sleeps 8
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Sunset and Ocean View in Key West's Truman Annex with 2 Bikes and Pool Access
2 bedrooms
1 bathroom
Sleeps 4
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Key West Found
2 bedrooms
2 bathrooms
Sleeps 6
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Condo in Old Town Key West's Truman Annex - Pool, Bicycle, Free Parking and WiFi
1 bedroom
1 bathroom
Sleeps 2
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Key West Beachfront Luxury 2/2 Condo A212 No Hurricane Damage
2 bedrooms
2 bathrooms
Sleeps 6
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67 other travelers have booked this property
Conch Get Enough! - Key West's Old Town Truman Annex
2 bedrooms
3 bathrooms
Sleeps 4
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Secret Villa I * Old Town with Private Pool, close to Duval!
3 bedrooms
3 bathrooms
Sleeps 6
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Shipyard Treasure
2 bedrooms
1 bathroom
Sleeps 4
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'CORAL CABANA' ~ Lush Porch Views of the Pool & Gardens, near Golf Course!
3 bedrooms
3 bathrooms
Sleeps 8
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Conch Wind
2 bedrooms
2 bathrooms
Sleeps 4
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The Mermaids House, Historic Old Town Key West
2 bedrooms
1 bathroom
Sleeps 4
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Tom's Chicken Coop: Nice Ocean View, Pool, Renovated, Close to Beach
2 bedrooms
2 bathrooms
Sleeps 6
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Secret Villa II * Old Town: Beautiful Home w/ Private Pool, 2 blocks to Duval!
3 bedrooms
3 bathrooms
Sleeps 6
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Truman Annex: The Plantation SELF CATERING beautifully landscaped rear patio
3 bedrooms
3 bathrooms
Sleeps 6
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Attitude Key West (2 Bikes and Wireless Internet)
2 bedrooms
1 bathroom
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Finn Key
2 bedrooms
1 bathroom
Sleeps 4
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'SOUTHERNMOST BELLE'~ Heated Pool, Gourmet Kitchen & Elegant Large Bedrooms!
5 bedrooms
4 bathrooms
Sleeps 10
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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
'CASA DE VINO' ~ Excellent Price for an Amazing Townhouse with Pool & Tiki!
3 bedrooms
3 bathrooms
Sleeps 8
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'LADY ADMIRAL' ~ Sweet cottage & guest house with private pool off Duval
3 bedrooms
3 bathrooms
Sleeps 8
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Harbour Place 115 in Truman Annex Key West
2 bedrooms
3 bathrooms
Sleeps 6
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Harbor Walk Hideaways
4 bedrooms
3 bathrooms
Sleeps 8
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Craig & Cindy Key West 3 Bedroom Waterfront Beachside Resort Condo
3 bedrooms
3 bathrooms
Sleeps 8
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Key West Gem - Large, Bright 2 BR Condo on Ocean w/ Olympic-size Pool
2 bedrooms
2 bathrooms
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Spectacular Atlantic Ocean View Condo (MONTHLY)
2 bedrooms
2 bathrooms
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27 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.