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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.

Spacious Waterfront Condo, 2/2 Pool, Dock, Pet OK
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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).

Old Town - Room Opens to Private Pool and Garden
SUPERHOST
Private room · 2 guests · 1 bed · 1 private bath

Old Town - Room Opens to Private 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.

Romantic Retreat - 2 person K Suite, Pvt deck/Spa!
SUPERHOST
Entire residential home · 2 guests · 1 bed · 1 bath

Romantic Retreat - 2 person K Suite, Pvt deck/Spa!Romantic Retreat is a free standing cottage which, in the 1800's, was the cistern for the Cigar Maker cottages here. It is decorated in a light Caribbean motif, efficiency kitchen (frig, microwave, hot plate) and a very airy bathroom with tub/shower. King memory foam bed and sleeps 2 persons only. 32” Smart TV (bring your Netflix, Amazon, etc. UN/PW). Bose Bluetooth speaker, Amazon Alexa provided. A private adjacent deck with a 2 person Solana spa/seating. Also handicapped accessible.

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

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Duval Retreat- Contemporary Duval Street Condo
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Key West Suites #202
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Honeymoon Hideaway, King bed, Private Deck & Spa!
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Duval Balcony - Suite Mischief
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Luxurious apartment with pool
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Bella Vita - 1B/1B Condo Just Steps from Duval
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Key West - Sunset ❀ The Green House
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Luxurious upstairs apartment with pool #3
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The Bartlum
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Mallory House Room #1
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Location, Location, Location! Cute and Convenient!
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Key West Suites #204

Pet-friendly houses

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Casa de Palmas - Old Town historic home with pool!
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Large Key West House
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Clean and Bright Key West Inspired Home Aug 15
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Paradise Palms
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The Eagle’s Nest (w/ heated pool)
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Tropical family-friendly home w/private pool, 1/2 block from Duval St. - dogs ok
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Private 2BR with Pool in Old Town Key West
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WYLAND PENTHOUSE- Luxury 2BDR Penthouse in prime Downtown location
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Charming cottage w/ private hot tub - 1 block from Duval, dogs OK!
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Family House, 2 K BR's, Private Spa/Deck, 2 pools.
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Harrison's Hideaway-Sleeps up to 4, K & F Sl Sofa!
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Recently renovated home w/ shared pool, furnished patio area - in town, dogs ok

Houses with pools

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Royal Poinciana Cottage-
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A Key West gem w/ a private pool - close to shops & restaurants, dog-friendly
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2/2 Old Town Waterfront Condo Pet Friendly
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*Casa Amelia* Pet friendly, Monthly Old Town home
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Caribbean Cottage - 2BR/2BA Sleeps 6, Heated Pools
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Renovated home w/ shared pool & furnished patio - near Duval Street, dogs ok
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Dog-friendly home w/ private pool offers fantastic location in central Key West
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Lovely dog-friendly home w/ mother-in-law cottage - great location, private pool
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Margarita Cottage-
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Family-friendly home w/ private pool, furnished patio, and parking - Dogs OK!
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Dog-friendly getaway w/ furnished patio & shared pool - blocks from the beach
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Historic Key West - Conch House - Sleeps 5

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