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 76 rentals matching your search criteria
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Shrimp Party

Type

  • Townhouse
Old Town
2 Bedrooms
2 Baths
4 Guests

Gated compound walking distance to Duval Street but behind the gates quiet solitude in your beautiful home with front porch overlooking the sparking pool.

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!

Tradewinds

Type

  • Condominium
Ocean Side
3 Bedrooms
2 Baths
6 Guests

A quick jaunt across the street takes you to Key West’s longest beach. A few blocks away you’ll discover dining and shopping galore on famous Duval Street. A short bike ride and you're at the Historic Seaport.

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!

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.

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!

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!

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.

Linger Longer

Type

  • Townhouse
Old Town
2 Bedrooms
1.5 Baths
5 Guests

Just imagine stepping out of the rental and stepping right into the pool!

Enjoy a carefree vacation in this beautifully decorated, 2 bedroom 1.5 bath, 2-story town home, located in the President's Walk of Truman Annex.

Conch Adventure

Type

  • Condominium
Old Town
2 Bedrooms
1 Bath
4 Guests

Nestled in a quiet corner of the Shipyard section in the desirable Truman Annex, this 2-bedroom 1 bath downstairs condo offers peace, quiet and convenience.

Bogey's Retreat

Type

  • Townhouse
Stock Island
2 Bedrooms
1.5 Baths
4 Guests

Additional outdoor space on your wrap around porch and large bricked patio to enjoy the tropical breezes.

Breezy Bungalow

Type

  • Townhouse
Old Town
2 Bedrooms
2.5 Baths
4 Guests

When a name says it all you know you have made the perfect choice for your Key West island escape.

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