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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 house · 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 house · 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
R5,655 ZAR per night
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Mango Hideaway steps off World Famous Duval street
R3,564 ZAR per night
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Honeymoon Hideaway, King bed, Private Deck & Spa!
R5,498 ZAR per night
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Duval Balcony - Suite Mischief
R4,841 ZAR per night
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Island Color Suite
R3,454 ZAR per night
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Luxurious apartment with pool
R1,520 ZAR per night
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Key West Suites Hotel -Adam Scott Rote Suite #203
R4,545 ZAR per night
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Bella Vita - 1B/1B Condo Just Steps from Duval
R2,763 ZAR per night
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Mallory House Room #1
R2,279 ZAR per night
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Location, Location, Location! Cute and Convenient!
R1,451 ZAR per night
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Cozy studio condo w/ shared pool & courtyard - easy beach access! Dogs OK!
R1,920 ZAR per night
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The Galleria~Unit 11 -- Recently Remodeled!
R2,295 ZAR per night

Pet-friendly houses

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Sweet Pea Cottage // 3 Bedroom Home located in Old Town!
R2,810 ZAR per night
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The Eagle’s Nest (w/ heated pool)
R2,542 ZAR per night
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Tropical family-friendly home w/private pool, 1/2 block from Duval St. - dogs ok
R13,248 ZAR per night
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WYLAND PENTHOUSE- Luxury 2BDR Penthouse in prime Downtown location
R5,871 ZAR per night
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Charming cottage w/ private hot tub - 1 block from Duval, dogs OK!
R6,838 ZAR per night
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Charming, Dog-Friendly Getaway w/ a Shared Pool, Free WiFi, Private Washer/Dryer
R2,127 ZAR per night
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Family House, 2 K BR's, Private Spa/Deck, 2 pools.
R7,294 ZAR per night
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Harrison's Hideaway-Sleeps up to 4, K & F Sl Sofa!
R5,498 ZAR per night
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Recently renovated home w/ shared pool, furnished patio area - in town, dogs ok
R2,473 ZAR per night
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Casa Cristol - Family Friendly Classic KW Charm
R7,628 ZAR per night
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Restored historic home w/ private pool & reserved off-street parking - Dogs OK!
R13,980 ZAR per night
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Duval Delight
R8,160 ZAR per night

Houses with pools

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Key West Hideaway, Sleeps 10, 4BR/4BA, Q Sl. Sofa!
R18,070 ZAR per night
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Royal Poinciana Cottage-
R2,992 ZAR per night
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A Key West gem w/ a private pool - close to shops & restaurants, dog-friendly
R11,701 ZAR per night
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Clean and Bright Key West Inspired Home
R2,141 ZAR per night
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Treasure Cove
R4,490 ZAR per night
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HUGE 5/6 with Pool, Beach and Offstreet Parking!
R18,857 ZAR per night
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Secret Villa II
R13,144 ZAR per night
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Southern Palms
R23,992 ZAR per night
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Angela’s Cottage/Private Pool/Pets Welcome/OldTown
R2,749 ZAR per night
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McCartney's Manor - Deluxe K Suite W/Pvt. Spa!
R5,498 ZAR per night
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Clean and Relaxing! 3 King Suites! With everything
R8,289 ZAR per night
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Robinson Crusoe Cottage
R3,406 ZAR per night

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