Key West Vacation Rentals

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Search nearly 100 Key West vacation rentals ranging from intimate 1 bedroom cottages to large 5 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 57 rentals matching your search criteria
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Casita de Catherine

Type

  • Cottage
Old Town
1 Bedroom
1 Bath
3 Guests

Enjoy Island life and live like a local in this perfect cottage on a quiet street in Key West. A welcoming outdoor space with a relaxing feel, this rental features a private hot tub and grill for outdoor entertaining.

Tropical Dreaming

Type

  • House
Old Town
2 Bedrooms
2.5 Baths
6 Guests

Do not look any further! Your perfect vacation home rental is right here! Offering a private pool with lounge chairs and covered outside porch. You can also bring your Fido!

Artist Garden

Type

  • House
Old Town
2 Bedrooms
2.5 Baths
4 Guests

This spacious home with a large outside deck is tucked away on a quiet lane in the Truman Annex, yet only a short walk to all attractions.

Bahamian Reed

Type

  • Townhouse
Old Town
2 Bedrooms
1.5 Baths
5 Guests

Look No Further!! Bahamian Reed is the vacation rental home for those special vacation memories that you will come back to again and again.

Lazy Gecko

Type

  • Condominium
Old Town
2 Bedrooms
1.5 Baths
4 Guests

Grab your bike and head for some fresh seafood at the Historic Seaport. Walk four blocks to bustling Duval Street to find the perfect t-shirt or enjoy a cold brew and people watch at a street view table.

Lavender Jungle

Type

  • Condominium
Old Town
2 Bedrooms
1 Bath
4 Guests

You are instantly soothed walking through the door of the Lavender Jungle, located in the Truman Annex, one of Key West's most attractive, quiet, and convenient neighborhoods.

Parrot Perch

Type

  • Condominium
Old Town
2 Bedrooms
2 Baths
5 Guests

Unbeatable location at a great price! The Parrot Perch is in the gated Shipyard Community of the prestigious Truman Annex.

A Siesta Bay

Type

  • Condominium
Old Town
2 Bedrooms
1 Bath
4 Guests

Here is your perfect opportunity to stay in one of the most popular complexes of Key West, the Truman Annex!

Sundown Refuge

Type

  • Condominium
Old Town
2 Bedrooms
2 Baths
5 Guests

View passing ships and sunsets from your own balcony in the Truman Annex’s most prestigious building!

Truman's Hideaway

Type

  • Condominium
Old Town
2 Bedrooms
2 Baths
5 Guests

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. But either way, you can enjoy breathtaking sunsets with a glass of wine from your own private porch.

Finn Key

Type

  • Condominium
Old Town
2 Bedrooms
1 Bath
4 Guests

Recently remodeled, tastefully decorated. This rental is hard to beat!

A Barefoot Retreat

Type

  • Condominium
Old Town
2 Bedrooms
1 Bath
4 Guests

No shoes needed at “A Barefoot Retreat” in the lovely Shipyard section of the historic Truman Annex private community. This two-bedroom, one bath, second floor condo will feel like your own tropical home the minute you walk through the door.

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