Key West Monthly Rentals

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Key West vacation homes, like the ones we offer, have been adored by many who have set foot on our sands. Harry S. Truman spent his winter down here, and Ernest Hemingway called the island his home for many years. We are proud to offer amazing Key West monthly rentals for guests who want to take full advantage of our beaches, ocean, and lifestyle for more than a weekend at a time. The option of a monthly rental allows guests to fully immerse themselves into Key West culture and enjoy the tropical beauty that surrounds them without having to make the commitment of buying real estate.

Ready to find your perfect vacation home in paradise? Please keep these things in mind while you search:

Displaying 25 - 36 of 36 rentals matching your search criteria
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Bye Bye Birdie

Type

  • Townhouse
Stock Island
3 Bedrooms
2 Baths
6 Guests

Find serenity in this pleasant and spacious home with tons of Key West charm. Featuring an abundance of back yard space for lounging or entertaining, you will not want to leave this lovely retreat.

Paradise Palms

Type

  • House
Old Town
2 Bedrooms
2 Baths
6 Guests

Make your next Florida vacation something special with this charming home in a quiet, upscale enclave that is close to everything!

Cottage by the Pool

Type

  • Townhouse
Stock Island
2 Bedrooms
1.5 Baths
4 Guests

In this cozy home you will find yourself nestled in the center of the Key West Golf Club on a secluded lane that cuts through the heart of its community.

Windchime

Type

  • Condominium
Old Town
0.5 Bedrooms
1 Bath
2 Guests

Searching for an affordable monthly vacation rental in the heart of Key West? Want to have your privacy and still enjoy the best that Paradise has to offer? Then just tune into the Windchime!

Wind Swept

Type

  • Townhouse
Stock Island
2 Bedrooms
1.5 Baths
6 Guests

Imagine yourself nestled within a serene, lushly landscaped picturesque community with walkways meandering around the only Caribbean golf course in the United States. All that and much more awaits you at Windswept!

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 Secret

Type

  • Condominium
Old Town
2 Bedrooms
1 Bath
4 Guests

Located in one of Key West’s historic and most cultural neighborhoods this lovely condominium will give you cause to celebrate the island way of life.

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.

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.

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.

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