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 17 rentals matching your search criteria
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Key Lime Pie

Type

  • Cottage
Old Town
2 Bedrooms
2 Baths
4 Guests

Key Lime Pie is the private cottage that perfectly encompasses the “Key West vibe” that you’re looking for. The minute you walk in to see the bright, sunny walls and local artwork, you know you are somewhere special.

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.

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!

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!

Paradise Place

Type

  • Condominium
Old Town
1 Bedroom
1 Bath
4 Guests

Cozy apartment within biking distance to The Historic Seaport, Cuban Coffee Queen, local grocery store Fausto's and even Higgs Beach.

Papa's Cottage Retreat

Type

  • House
Old Town
1 Bedroom
1 Bath
2 Guests

As you step through the natural wooden gate onto the brick pathway, you will be embraced by this private garden oasis.

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!

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.

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.

A Little Slice Of Paradise

Type

  • Townhouse
Stock Island
2 Bedrooms
1.5 Baths
5 Guests

Located on the main road meandering through the secluded gated Key West Golf Club community, you’ll find A Little Slice of Paradise. Spend a month (or two) in this charming townhouse and you may never return home.

Tropical Casita

Type

  • House
Old Town
1 Bedroom
2 Baths
2 Guests

If privacy is what you desire this is the property for you. Completely set back from street and fenced for you to enjoy your private pool and large outdoor space.

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.

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