Key West Vacation Rentals

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Search nearly 100 Key West vacation rentals ranging from intimate 2 bedroom cottages to large 6 bedroom homes. With properties in popular Key West communities like Truman Annex, Key West Golf Club, and 1800 Atlantic plus a variety of pet friendly and monthly rentals, we are sure we have the perfect fit for your trip. Our local Key West team of vacation rental experts has been helping travelers plan amazing vacations for decades and loves to share their local knowledge. Don't hesitate to contact us with questions or for help finding the perfect rental and booking your Key West vacation!

Displaying 1 - 12 of 41 rentals matching your search criteria
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Mermaid's Dream

Type

  • Condo
2 Bedrooms
2 Baths
4 Guests
Ocean views from your wrap around balcony and the Olympic sized pool await you at this beautiful home.

Sunny View

Type

  • Cottage
1 Bedroom
2 Baths
2 Guests
Lovely 1 bed/2 bathroom private home with covered back porch and bricked courtyard within walking distance to Duval Street.

Shrimp Party

Type

  • Townhouse
2 Bedrooms
2 Baths
4 Guests
Gated compound walking distance to Duval Street but behind the gates quiet solitude in your beautiful home with front porch overlooking the sparking pool.

William's Loft

Type

  • Cottage
2 Bedrooms
1 Bath
3 Guests
Private outdoor space to enjoy this unique cottage within walking distance of great restaurants and shops.

Hidden Treasure

Type

  • Condo
2 Bedrooms
2 Baths
4 Guests
Private outdoor kitchen to able to enjoy cooking your favorite dish while enjoying the large outdoor space.

Ibis

Type

  • Cottage
1 Bedroom
1 Bath
2 Guests
Enjoy your private front porch in this quiet neighborhood in Old Town Key West. Located in The Colony compound, Ibis is a wonderful one bedroom one bath Key West rental home.

Emma's Escape

Type

  • Condo
2 Bedrooms
1 Bath
4 Guests
Lounge your days away by the pool or enjoy the peace and quiet away from the hustle and bustle of Duval Street.

A Little Slice Of Paradise

Type

  • Townhouse
2 Bedrooms
1.5 Baths
6 Guests
Townhouse located just steps from the Key West Golf Course Club House and after a round of golf head over to either of the two pools to cool off.

Tropical Casita

Type

  • Home
1 Bedroom
2 Baths
2 Guests
If privacy is what you desire this is the property for you. Completely set back from street and fenced for you to enjoy your private pool and large outdoor space.

Lazy Gecko

Type

  • Condo
2 Bedrooms
1.5 Baths
4 Guests
Beautifully recently remodeled 2 bed/1.5 bath condo located just 4 blocks to Duval Street and the Historic Seaport.

Verandah

Type

  • Home
2 Bedrooms
2.5 Baths
4 Guests
Beautifully designed yet comfortable private home that you may never leave, only to go outside to your private pool and secluded space to hang out.

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