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:

  • Make sure your dates are for a 30 night stay or your search may return no results
  • If you are searching during peak season (Jan, Feb, Mar, Apr), all rentals require an arrival date of the first of the month
  • If your search doesn't return the properties you are expecting, please call one of our reservationists at 305-296-2594 for assistance
  • Use the search filters to narrow the list of properties to match your specific requirements
  • If you find the perfect monthly rental, feel free to book online. You will be contacted by our reservations department to confirm the booking
  • Any questions? Don’t hesitate to contact us for additional information and to assist you in reserving your favorite property
Displaying 13 - 24 of 34 rentals matching your search criteria
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Shrimp Party

Type

  • Townhouse
2 Bedrooms
2 Baths
4 Guests
Gated compound walking distance to Duval Street but behind the gates quiet solitude in your beautiful home with front porch overlooking the sparking pool.

Duval On The Square

Type

  • Townhouse
2 Bedrooms
2.5 Baths
6 Guests
Rooftop community just steps away from Duval Street to great restaurants, shopping and entertainment.

Mermaid's Dream

Type

  • Condo
2 Bedrooms
2 Baths
4 Guests
Ocean views from your wrap around balcony and the Olympic sized pool await you at this beautiful home.

Conch Republic Retreat

Type

  • Cottage
2 Bedrooms
2 Baths
4 Guests
Historic conch home located in The Meadows, a sought out quiet neighborhood, to enjoy your private pool and outdoor space.

Coconut Cottage

Type

  • Cottage
1 Bedroom
2 Baths
2 Guests
Private fenced outdoor space to enjoy your private plunge pool and the large outdoor space for lounging and dining.

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.

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.

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.

Poolside Paradise

Type

  • Home
2 Bedrooms
2 Baths
4 Guests
It is all about outdoor living at this beautiful private home with large covered living space overlooking your private pool.

A Little Slice Of Paradise

Type

  • Townhouse
2 Bedrooms
1.5 Baths
6 Guests
Townhouse located just steps from the Key West Golf Course Club House and after a round of golf head over to either of the two pools to cool off.

Cayo Hueso Sunshine

Type

  • Home
2 Bedrooms
3 Baths
6 Guests
French doors leading from your kitchen to this homes beautiful outdoor space with porches, deck and private pool.

True Paradise

Type

  • Condo
2 Bedrooms
2 Baths
4 Guests
Located in one of the most sought out neighborhoods "The Meadows" this lovely condo has everything you need to enjoy your time in Key West.

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