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Key West Vacation Rentals

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202 rentals in Key West.
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Penthouse
#1 of 2 pools with waterfall
Penthouse
Living room
Guest House
Exterior view and parking
6 bedroom Duval Street Compound - Pool, Hot Tub, 2 parking spots - A++ Location
Rental Home
6 bedrooms
7 bathrooms
Sleeps 16
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Sunrise Suite Key West 2 Bed Rooms 2 Full Baths
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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Patio View
La Brisa Pool
Oceanfront 2 Bedroom 2 Bath Condo Key West Florida
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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Casa Del Sol, a Key West Vacation
Front of Home
Paradise Awaits You! Casa Del Sol
Casa Del Sol, a Key West Vacation (Truman Annex)
Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
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Beautiful tranquil heated pool steps from your door.
Private patio, lush landscaping
Artist Cottage in Truman Annex
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
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The Tree House Old Town 2 Bedroom MONTHLY Rental
Rental Home
2 bedrooms
1 bathroom
Sleeps 7
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Casa Cay West ~ Beautiful Tropical House - 2 King Beds! Sleeps 8
Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Sunset and Ocean View in Key West's Truman Annex with 2 Bikes and Pool Access
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
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Condo in Old Town Key West's Truman Annex - Pool, Bicycle, Free Parking and WiFi
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
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Secret Villa II * Old Town: Beautiful Home w/ Private Pool, 2 blocks to Duval!
Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
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STARFISH - SUNNY TOWNHOME in QUIET TRUMAN ANNEX TWO BLOCKS FROM DUVAL ST.
Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
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'LOST SHAKER OF SALT' ~ 3 Bed, 2 Bath Pet Friendly with 40' Private Pool
Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
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Attitude Key West (2 Bikes and Wireless Internet)
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
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'Oceanside Oasis' * Kings Pointe: Direct Ocean Views & 3 BR'S
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
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My Condo by the Beach with Ocean View
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
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2022 IS THE FINAL YEAR. Giving it to a vacation rental company for 2023.
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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Sea Breeze Cottage- in Beautiful Truman Annex
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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2022 IS THE FINAL YEAR. Giving it to a vacation rental company for 2023.
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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Truman Annex: The Plantation SELF CATERING beautifully landscaped rear patio
Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
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Secret Villa I * Old Town with Private Pool, close to Duval!
Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
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Seaside Place Key West FL 5 Bedroom House 4 Baths
Rental Home
5 bedrooms
4 bathrooms
Sleeps 12
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Catherine House: A charming Old Town Key West cottage
Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
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Attitude Key West at the Beach, 2 Bikes and Internet, Pool, Whirl Pool, Sauna
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
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William Skelton House - Available Easter Weekend!
Rental Home
6 bedrooms
4 bathrooms
Sleeps 14
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Top Floor Ocean Views from every window Olympic Size Pool-Jacuzzi- Sauna-Tennis
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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Quaint Island Escape Condo w/Spacious Balcony Deck in Beautiful Truman Annex
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
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Boli Townhouse - Luxury Rental in gated Truman Annex
Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
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The Mermaids House, Historic Old Town Key West
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
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Harbour Place 115 in Truman Annex Key West
Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 6
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Azure Morning- Oceanfront, near Marina, Pool & Jacuzzi
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
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Key West Beachfront Luxury 2/2 Condo A212 No Hurricane Damage
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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Conch Haven Old Town 1/1 MONTHLY Rental
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
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Rose Lane Villas - Villa Vista - 2 bedrooms - Downtown Key West
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Enjoy More Privacy in a Truman Annex End Unit Townhome
Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
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'CORAL CABANA' ~ Lush Porch Views of the Pool & Gardens, near Golf Course!
Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
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Duval Square Penthouse: A large, beautiful condo steps from the action
Condo/Apartment
4 bedrooms
5 bathrooms
Sleeps 10
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Villa Paradiso: A unique mid-town paradise
Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
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Apple of Your Eye in Paradise (Truman Annex)!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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NEWLY RENOVATED ...LAST MINUTE SPECIALS...CHECK DATES
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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Ann Street Cottage: A bright and airy home near Duval Street
Rental Home
1 bedroom
2 bathrooms
Sleeps 2
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'LADY ADMIRAL' ~ Sweet cottage & guest house with private pool off Duval!
Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
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Rose Lane Villas - Villa Grande - 3 bedrooms - Downtown Key West
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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BARGAIN RATES! Pool, wifi, renovated 2/2 1/2 private courtyard.
Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Beach House with Ocean View-No Contact Check-In
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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'CASA DE VINO' ~ Excellent Price for an Amazing Townhouse with Pool & Tiki!
Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
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Lazy River Pool, Enchanting Garden, Old Town Key West, Free WiFi, Bikes & Parkin
Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
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Peaceful Setting Amongst The Active Island Life Style
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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~$~1,500/wk - Best Deal in Key West - Plus 7 Bikes Included!
Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 6
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Duval Square Retreat: A beautiful condo steps from the action
Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Conch Retreat in Beautiful Truman Annex with 2 Bikes
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
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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.