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 34 rentals matching your search criteria
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The Gallery

Type

  • Townhouse
2 Bedrooms
2.5 Baths
4 Guests
You are so close to the large community pool that you will be able to hear the waterfall in this beautifully landscaped area.

First Breath

Type

  • Home
3 Bedrooms
2 Baths
6 Guests
Bring the family to this 3 bed, 2 bath private conch home and enjoy your large private pool and outdoor area as the days pass by.

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.

Ecco Domani

Type

  • Home
3 Bedrooms
2.5 Baths
6 Guests
Beautifully designed and decorated this private home has the gourmet kitchen with French doors that lead to your private outdoor space and pool.

Cayo Hueso Sunshine

Type

  • Home
2 Bedrooms
3 Baths
6 Guests
French doors leading from your kitchen to this homes beautiful outdoor space with porches, deck and private pool.

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.

Flagler Station

Type

  • Home
3 Bedrooms
2 Baths
8 Guests
With family in mind this lovely 3 bed, 2 bath private home has plenty to offer with a private outdoor space and pool to spend your days enjoying.

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.

Coral Breeze

Type

  • Townhouse
2 Bedrooms
1.5 Baths
4 Guests
Perfect view from your screened porch to watch golfers play the first hole on the Rees Jones designed Key West Golf Course.

Coconut Cottage

Type

  • Cottage
1 Bedroom
2 Baths
2 Guests
Private fenced outdoor space to enjoy your private plunge pool and the large outdoor space for lounging and dining.

Wind Swept

Type

  • Townhouse
2 Bedrooms
1.5 Baths
6 Guests
Screened porches up and down for you to enjoy the the extra living space in this lovely townhome.

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