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Vacation rental houses in Key West

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Top-rated houses in Key West

Guests agree: these stays are highly rated for location, cleanliness, and more.

Old Town - Room Opens to Pool and Garden
SUPERHOST
Private room · 2 guests · 1 bed · 1 private bath
Old Town - Room Opens to Pool and GardenLocated in the heart of Old Town, we are three blocks from Duval Street, a 10-minute walk to Higgs Beach, and around the corner from the best, least-expensive meal in town--El Siboney Cuban Restaurant. We suggest bicycling around Key West. Rentals from We-Cycle Bike Shop can be delivered to our door. Two blocks away, The Duval Loop offers free air-conditioned bus service 7 a.m. until midnight. We also offer a link with recommendations for excursions, tours, & restaurants.
Get Away
Private room · 2 guests · 1 bed · 1 private bath
Get AwayProperty Location - When you stay at Getaway and Va cay in Paradise you will be on the beach and Key West downtown within minutes. Airport and popular locations are near by. The Room - Make yourself at home with central AC, TV, internet access, and cable programming for your entertainment.
Spacious Waterfront Condo, 2/2 Pool, Dock, Pet OK
SUPERHOST
Entire residential home · 6 guests · 3 beds · 2 baths
Spacious Waterfront Condo, 2/2 Pool, Dock, Pet OKTime to relax! Bring your family & friends to this 1350 sqft Waterfront home at Pelican Landing. Boat slips available on site with commercial ice machine, fish cleaning station and BBQ grills. Located in historic Downtown Key West. Walk/Bike everywhere 1mi to Duval Street, Historic Seaport, Hemingway House, etc. On-site amenities: heated pool, tiki bar & grill, bike rentals, parking, secure keyless entry, & private elevator. Large park adjacent with tennis courts. 10min from airport (EYW).

Vacation rentals for every style

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Popular house amenities in Key West

  • Pool
  • Air conditioning
  • Kitchen
  • Wifi
  • Pets allowed

Apartments in Key West

SUPERHOST
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Mallory House Room #2
SUPERHOST
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Duval Balcony - Street Suite
SUPERHOST
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Key West Suites #201
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The Galleria~Unit #14 - Recently Remodeled!
SUPERHOST
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Bella Vita - 1B/1B Condo Just Steps from Duval
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Luxurious upstairs apartment with pool #3
SUPERHOST
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Duval Balcony - Suite Mischief
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Duval Balcony Spanky's Retreat
SUPERHOST
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Key West Suites #202
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Studio condo w/ entertainment, full kitchen & private parking - central location
SUPERHOST
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Duval Retreat- Contemporary Duval Street Condo
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Studio suite w/ shared hot tubs, patio, kitchenette - steps from beach. Dogs OK!

Pet-friendly houses

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Peaceful home w/ yard, hot tub, off street-parking
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WYLAND PENTHOUSE- Luxury 2BDR Penthouse in prime Downtown location
SUPERHOST
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Casa Cristol - Family Friendly Classic KW Charm
SUPERHOST
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Romantic Retreat - 2 person K Suite, Pvt deck/Spa!
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Charming house w/ private patio - great central location, dogs OK
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Charming cottage w/ private hot tub - 1 block from Duval, dogs OK!
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Duval Delight
SUPERHOST
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Private 2BR with Pool in Old Town Key West
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Porchside Paradise
SUPERHOST
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Harrison's Hideaway-Sleeps up to 4, K & F Sl Sofa!
SUPERHOST
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Lennon's Lodge, Luxury Accommodations for up to 6!
SUPERHOST
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Downtown Waterfront Penthouse Pool, Parking, Dock

Houses with pools

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Recently renovated home w/ shared pool, furnished patio area - in town, dogs ok
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Royal Poinciana Cottage-
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Luxurious, beautiful house with large heated pool-
SUPERHOST
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Heart of Key West, house + cottage = Resort FUN!!!
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Renovated home w/ shared pool & furnished patio - near Duval Street, dogs ok
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Robinson Crusoe Cottage- Shared Pool
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Spacious home with pool, balcony, and a block from Duval Street
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Newly remodeled family home with a shared swimming pool and fitness center!
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Restored historic home w/ private pool & reserved off-street parking - Dogs OK!
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Joan's Caribbean Hideaway
SUPERHOST
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Clean and Bright Key West Inspired Home/ Dec 2
SUPERHOST
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Historic Key West - Cigar House - Sleeps 4