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 48 rentals matching your search criteria
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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.

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.

Casa Grande

Type

  • House
Old Town
5 Bedrooms
5.5 Baths
12 Guests

Perfect for an extended family or group of friends, this property offers great amenities including private pool, and close proximity to many Key West attractions!

Treetop Paradise

Type

  • Condominium
Old Town
2 Bedrooms
2 Baths
4 Guests

Located in the historic Bahama Village neighborhood, nestled amongst the palms, you‘ll find the stately building that houses Treetop Paradise.

Tranquility

Type

  • Cottage
Old Town
1 Bedroom
1.5 Baths
4 Guests

Settled in a small community of Old Town yet only a short walk to Duval Street, this lovely cottage offers everything you can expect from a perfect Key West rental.

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.

Southard Square Hideaway

Type

  • Condominium
Old Town
1 Bedroom
1 Bath
4 Guests

A quiet oasis in Old Town Key West that offers a beautiful shared pool and off street parking.

Atlantic Paradise

Type

  • Condominium
Ocean Side
2 Bedrooms
2 Baths
6 Guests

Imagine swimming in the Olympic sized pool and enjoying a spectacular view of the Atlantic Ocean at the same time. How about an evening stroll through the tropical jungle in your own backyard.

Coral Breeze

Type

  • Townhouse
Stock Island
2 Bedrooms
1.5 Baths
4 Guests

For the golfer in the family and for those who just want an idyllic vacation spot, Coral Breeze is the perfect choice!

Under The Palms

Type

  • House
Mid Town
2 Bedrooms
2 Baths
4 Guests

Meander down a quiet street in midtown Key West until you come upon a white picket fence on a shady corner lot. Park and walk around to open the gate.

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.

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