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 27 rentals matching your search criteria
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Southard Getaway

Type

  • Condominium
Old Town
2 Bedrooms
1.5 Baths
5 Guests

“Amazingly Perfect!” That is how one of our delighted guests reviewed Southard Getaway and we’re sure you’ll agree. Imagine arriving in Key West to this beach-like home within walking distance of all that Key West has to offer.

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.

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.

Shipyard Treasure

Type

  • Condominium
Old Town
2 Bedrooms
1 Bath
4 Guests

Finding a perfect property for your family vacation is easier said than done, but this contemporary condo at Truman Annex might just be the one.

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.

Key West Casa

Type

  • Townhouse
Old Town
3 Bedrooms
2 Baths
6 Guests

This spacious 3 bedroom apartment is located in Shipyard of Truman Annex, one of the most desirable Key West communities, close to Blue Heaven and Santiago's Bodega, one of Key West most popular restaurants.

Alluring Porches

Type

  • Townhouse
Old Town
3 Bedrooms
3 Baths
6 Guests

Feel the tropical allure of this spacious home in the center-of-it-all community of the historic 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!

Buena Vista

Type

  • Townhouse
Old Town
2 Bedrooms
2.5 Baths
6 Guests

The historic brick foundry residence is in the luxurious gated community of the Truman Annex, appropriately named after President Harry Truman.

City Cay

Type

  • Condominium
Old Town
1 Bedroom
1 Bath
2 Guests

Looking for a cozy, quiet spot for just the two of you with all the modern conveniences of home? This understated Truman Annex Condo is the place!

A Place In Paradise

Type

  • Townhouse
Old Town
2 Bedrooms
2.5 Baths
6 Guests

Located on Porter Lane of Truman Annex you can find your real PLACE IN PARADISE!

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