Key West Vacation Rentals

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Search nearly 100 Key West vacation rentals ranging from intimate 1 bedroom cottages to large 5 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 57 rentals matching your search criteria
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La Casita

Type

  • House
Old Town
2 Bedrooms
1 Bath
4 Guests

The location of La Casita cannot be beat -- right in the heart of Old Town yet on a quiet lane, only steps to Duval Street. This property is a monthly rental only. Sleeps 4 people.

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.

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.

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.

Ecco Domani

Type

  • House
Old Town
3 Bedrooms
2.5 Baths
6 Guests

A beautiful three-story home with private pool, off street parking, and attractive decor, Ecco Domani is a wonderful Key West escape that you will want to come home to year after year.

Casita de Catherine

Type

  • Cottage
Old Town
1 Bedroom
1 Bath
3 Guests

Enjoy Island life and live like a local in this perfect cottage on a quiet street in Key West. A welcoming outdoor space with a relaxing feel, this rental features a private hot tub and grill for outdoor entertaining.

Osprey

Type

  • Cottage
Old Town
0.5 Bedrooms
1 Bath
2 Guests

Great location, great price! Osprey is the perfect getaway rental for a couple who wants to enjoy everything Key West has to offer!

Bahamian Reed

Type

  • Townhouse
Old Town
2 Bedrooms
1.5 Baths
5 Guests

Look No Further!! Bahamian Reed is the vacation rental home for those special vacation memories that you will come back to again and again.

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.

Emma's Escape

Type

  • Condominium
Old Town
2 Bedrooms
1 Bath
4 Guests

Lounge your days away by the pool or enjoy the peace and quiet away from the hustle and bustle of Duval Street.

Casa Grande

Type

  • House
Old Town
5 Bedrooms
5.5 Baths
12 Guests

Perfect for large families or groups of friends, this property offers great amenities including a private pool, open floor plan, 2 kitchens and a large laundry room, right downtown Key West.

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.

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