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 1 - 12 of 21 rentals matching your search criteria
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Conch Republic Retreat

Type

  • Cottage
Old Town
2 Bedrooms
2 Baths
4 Guests

Located in the quiet neighborhood of The Meadows, you’ll find the Conch Republic Retreat, a quintessential cigar maker’s shotgun style house, circa 1890.

Casa de Rosalie

Type

  • House
Old Town
3 Bedrooms
2 Baths
8 Guests

Built in 1889 with original Dade County Pine, history comes alive when you enter this luxurious private home.

Lazy Gecko

Type

  • Condominium
Old Town
2 Bedrooms
1.5 Baths
4 Guests

Grab your bike and head for some fresh seafood at the Historic Seaport. Walk four blocks to bustling Duval Street to find the perfect t-shirt or enjoy a cold brew and people watch at a street view table.

Land Of Love

Type

  • Townhouse
Old Town
2 Bedrooms
1.5 Baths
4 Guests

Your perfect escape to Key West awaits you in the Land of Love.

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.

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.

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.

Perfect Pineapple

Type

  • House
Old Town
2 Bedrooms
1 Bath
4 Guests

Long considered a sign of hospitality, the pineapple is widely recognized as sign of Welcome and Friendship, and so we welcome YOU to the Perfect Pineapple!

First Breath

Type

  • House
Old Town
3 Bedrooms
2 Baths
6 Guests

Bring the family to this 3 bed, 2 bath private conch home and enjoy your large private pool and outdoor area as the days pass by.

Tumi's Time Out

Type

  • Townhouse
Old Town
2 Bedrooms
2 Baths
4 Guests

Tumi’s Time Out is a 2-bedroom, 2-bathroom town-home in the sought after Windward Park location. A secluded compound that is a tropical hideaway, surrounded by lush palms and balmy breezes.

Boat House

Type

  • Cottage
Old Town
1 Bedroom
2 Baths
2 Guests

Step into a tranquil community on a quiet lane and discover the Boat House, a nautically themed treasure in Old Town Key West.

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