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 13 - 24 of 27 rentals matching your search criteria
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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!

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!

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.

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.

Conch Condo

Type

  • Condominium
Old Town
2 Bedrooms
2 Baths
5 Guests

Perfect rental for a small family or couple of friends, close proximity to the pool and beach, Conch Condo makes one of the most desirable vacation rentals. A two-bedroom, two-bath condo, second floor condo in Truman Annex.

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.

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!

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.

Easy Livin'

Type

  • House
Old Town
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.

Finn Key

Type

  • Condominium
Old Town
2 Bedrooms
1 Bath
4 Guests

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

Sunset Celebration

Type

  • Condominium
Old Town
2 Bedrooms
1 Bath
4 Guests

This unit, aptly named Sunset Celebration, is close to Mallory Square, the perfect place to enjoy the local festivities that close the day every night.

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