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 38 rentals matching your search criteria
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Casa de Rosalie

3 Bedrooms
2 Baths
8 Guests
Private home that accommodates 8 guests to enjoy the large outdoor dining area while viewing your private pool in your fenced yard.

Coral Breeze

Type

  • Townhouse
2 Bedrooms
1.5 Baths
4 Guests
Perfect view from your screened porch to watch golfers play the first hole on the Rees Jones designed Key West Golf Course.

Southard Square Hideaway

Type

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

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.

Lighthouse Villa

Type

  • Home
3 Bedrooms
4.5 Baths
8 Guests
In the midst of many historic sites this home has all the updated amenities for you and your family to enjoy plus be within walking distance of the Southernmost Point.

Emma's Secret

Type

  • Condo
2 Bedrooms
1 Bath
4 Guests
Lush tropical outdoor setting within this small compound, privacy as you enjoy the pool and outdoor gardens.

Wind Swept

Type

  • Townhouse
2 Bedrooms
1.5 Baths
6 Guests
Screened porches up and down for you to enjoy the the extra living space in this lovely townhome.

Kokomo

Type

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

Treetop Paradise

2 Bedrooms
2 Baths
4 Guests
Small quiet compound with a pool an off street parking, walking distance to great restaurants, shopping and entertainment.

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