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 37 - 48 of 67 rentals matching your search criteria
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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.

Lighthouse Villa

Type

  • Home
3 Bedrooms
4.5 Baths
8 Guests
In the midst of many historic sites this home has all the updated amenities for you and your family to enjoy plus be within walking distance of the Southernmost Point.

Casa de Rosalie

3 Bedrooms
2 Baths
8 Guests
Private home that accommodates 8 guests to enjoy the large outdoor dining area while viewing your private pool in your fenced yard.

Truman's Hideaway

Type

  • Condo
2 Bedrooms
2 Baths
5 Guests
Enjoy breathtaking sunsets with a glass of wine from your own private porch

It's hard to say which is more impressive, the view of Florida Bay from your private deck or living in front of Truman's Little White House.

Southard Square Hideaway

Type

  • Condo
1 Bedroom
1 Bath
4 Guests
Quiet oasis in Old Town Key West that offers a beautiful shared pool and off street parking.

Perfect Pineapple

Type

  • Home
2 Bedrooms
1 Bath
4 Guests
Sit along side your private pool for morning coffee or your evening glass of wine.

Conch Republic Retreat

Type

  • Cottage
2 Bedrooms
2 Baths
4 Guests
Historic conch home located in The Meadows, a sought out quiet neighborhood, to enjoy your private pool and outdoor space.

Duval Penthouse

Type

  • Home
3 Bedrooms
2.5 Baths
7 Guests
Location, location, location! Practically overlooking famous Duval Street from large upstairs deck!

Sunset Celebration

Type

  • Condo
2 Bedrooms
1 Bath
4 Guests
Beautiful, recently updated 2 bedroom apartment located in a popular community of Truman Annex, only a short bike ride to Fort Zachary Taylor Beach

Easy Livin'

Type

  • Home
3 Bedrooms
4 Baths
8 Guests
Cozy, but upscale, this charming vacation rental with a private pool and great outside space is guaranteed to make you feel right at home.

The name says it all!

Crowner's Jewel

Type

  • Townhouse
2 Bedrooms
2.5 Baths
6 Guests
Imagine being able to walk to the Sunset Celebrations every single evening! Only couple blocks to Mallory Square you can find this true gem!

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