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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
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).

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
G$95,460 per night
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Key West Suites #202
G$66,217 per night
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Honeymoon Hideaway, King bed, Private Deck & Spa!
G$89,460 per night
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Duval Balcony - Suite Mischief
G$65,483 per night
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Key West Suites #201
G$62,872 per night
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Luxurious apartment with pool
G$22,992 per night
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Key West - Sunrise ❀ The Green House
G$51,981 per night
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Key West - Sunset ❀ The Green House
G$50,486 per night
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Bella Vita - 1B/1B Condo Just Steps from Duval
G$44,790 per night
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Luxurious upstairs apartment with pool #3
G$68,648 per night
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The Bartlum
G$81,636 per night
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Mallory House Room #1
G$33,591 per night

Pet-friendly houses

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Casa de Palmas - Old Town historic home with pool!
G$25,738 per night
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Large Key West House
G$41,804 per night
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Paradise Palms
G$44,103 per night
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Clean and Bright Key West Inspired Home Aug 15
G$37,414 per night
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The Eagle’s Nest (w/ heated pool)
G$38,877 per night
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Tropical family-friendly home w/private pool, 1/2 block from Duval St. - dogs ok
G$229,710 per night
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Private 2BR with Pool in Old Town Key West
G$68,976 per night
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WYLAND PENTHOUSE- Luxury 2BDR Penthouse in prime Downtown location
G$88,832 per night
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Charming cottage w/ private hot tub - 1 block from Duval, dogs OK!
G$115,796 per night
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Family House, 2 K BR's, Private Spa/Deck, 2 pools.
G$114,542 per night
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Harrison's Hideaway-Sleeps up to 4, K & F Sl Sofa!
G$89,460 per night
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Recently renovated home w/ shared pool, furnished patio area - in town, dogs ok
G$58,316 per night

Houses with pools

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Royal Poinciana Cottage-
G$45,267 per night
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A Key West gem w/ a private pool - close to shops & restaurants, dog-friendly
G$199,194 per night
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Treasure Cove
G$67,931 per night
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2/2 Old Town Waterfront Condo Pet Friendly
G$83,607 per night
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Caribbean Cottage - 2BR/2BA Sleeps 6, Heated Pools
G$57,480 per night
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Renovated home w/ shared pool & furnished patio - near Duval Street, dogs ok
G$72,320 per night
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Dog-friendly home w/ private pool offers fantastic location in central Key West
G$46,820 per night
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Lovely dog-friendly home w/ mother-in-law cottage - great location, private pool
G$226,784 per night
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Family-friendly home w/ private pool, furnished patio, and parking - Dogs OK!
G$191,460 per night
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Margarita Cottage-
G$45,267 per night
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Dog-friendly getaway w/ furnished patio & shared pool - blocks from the beach
G$67,513 per night
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Historic Key West - Conch House - Sleeps 5
G$152,075 per night

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