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 30 rentals matching your search criteria
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Bahamian Reed

Type

  • Townhouse
2 Bedrooms
1.5 Baths
5 Guests
Look No Further!! Bahamian Reed is a vacation rental home that you will come back to again and again

2 bedroom 1.5 bathroom townhome located in Truman Annex in Old Town Key West.

The Dolphin House

Type

  • Home
4 Bedrooms
3.5 Baths
8 Guests
Wonderful for larger groups or family get togethers, The Dolphin House offers a roomy vacation home in one of Key West's most desirable locations, Truman Annex.

Southard Getaway

Type

  • Condo
2 Bedrooms
1.5 Baths
5 Guests
Amazingly Perfect!!! That is how one of our guests reviewed Southard Getaway! This amazingly perfect rental can be yours as well!

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!

Finn Key

Type

  • Condo
2 Bedrooms
1 Bath
4 Guests
Just steps away from the pool! Recently remodeled, tastefully decorated. This rental is hard to beat!

The Hemingway

Type

  • Townhouse
2 Bedrooms
2 Baths
4 Guests
The location does not get better than this! Short bike ride to the beach and walking distance to most restaurants and shops!

Breezy Bungalow

Type

  • Townhouse
2 Bedrooms
2.5 Baths
4 Guests
Looking for a nice home in Truman Annex community? Breezy Bungalow is the answer for you!

Conch Adventure

Type

  • Condo
2 Bedrooms
1 Bath
4 Guests
Come enjoy one of Key West's most desirable rental complexes, Truman Annex. Conveniently located just couple blocks to the beach, Duval Street and Mallory Square, makes this the ideal rental for a small family or couple of friends

Conch Condo

Type

  • Condo
2 Bedrooms
2 Baths
4 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 in Truman Annex.

City Cay

Type

  • Condo
1 Bedroom
1 Bath
2 Guests
Recently renovated, modern and cozy upstairs apartment with a large balcony overlooking the neighborhood

Captains Wheel

Type

  • Townhouse
2 Bedrooms
2.5 Baths
6 Guests
Beautiful 2 bedroom, 2.5 bath vacation rental. Enjoy the convenient proximity to most events Key West has to offer!

Sundown Refuge

Type

  • Condo
2 Bedrooms
2 Baths
5 Guests
View passing ships and sunsets from your own deck or balcony in the Truman Annex’s most prestigious building

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