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 1 - 12 of 32 rentals matching your search criteria
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Ibis

Type

  • Cottage
1 Bedroom
1 Bath
2 Guests
Enjoy your private front porch in this quiet neighborhood in Old Town Key West. Located in The Colony compound, Ibis is a wonderful one bedroom one bath Key West rental home.

Southard Square Hideaway

Type

  • Condo
1 Bedroom
1 Bath
4 Guests
A quiet oasis in Old Town Key West that offers a beautiful shared pool and off street parking.

Kokomo

Type

  • Townhouse
2 Bedrooms
2.5 Baths
4 Guests
Steps away from the large lagoon style pool surrounded w/lush tropical landscape.

Wind Swept

Type

  • Townhouse
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!

Papa's Cottage Retreat

Type

  • Cottage
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.

A Suite Paradise

Type

  • Home
3 Bedrooms
2 Baths
6 Guests
Private home with large covered outdoor living area overlooking your private pool w/waterfall.

La Casita

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.

Paradise Palms

Type

  • Cottage
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!

Sunny View

Type

  • Cottage
1 Bedroom
2 Baths
2 Guests
Lovely 1 bed/2 bathroom private home with covered back porch and bricked courtyard within walking distance to Duval Street.

Poolside Paradise

Type

  • Home
2 Bedrooms
2 Baths
4 Guests
Spending time in the warm breezes of Key West – isn’t that why you come here? At Poolside Paradise you can enjoy outdoor living at its best!

Ecco Domani

Type

  • Home
3 Bedrooms
2.5 Baths
6 Guests
Beautifully designed and decorated this private home has the gourmet kitchen with French doors that lead to your private outdoor space and pool.

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