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 39 rentals matching your search criteria
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William's Loft

Type

  • Cottage
2 Bedrooms
1 Bath
3 Guests
Private outdoor space to enjoy this unique cottage within walking distance of great restaurants and shops.

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.

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.

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.

Verandah

Type

  • Home
2 Bedrooms
2.5 Baths
4 Guests
Beautifully designed yet comfortable private home that you may never leave, only to go outside to your private pool and secluded space to hang out.

Flagler Station

Type

  • Home
3 Bedrooms
2 Baths
8 Guests
With family in mind this lovely 3 bed, 2 bath private home has plenty to offer with a private outdoor space and pool to spend your days enjoying.

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.

Tropical Casita

Type

  • Home
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.

Perfect Pineapple

Type

  • Home
2 Bedrooms
1 Bath
4 Guests
Sit along side your private pool for morning coffee or your evening glass of wine.

Spa Oasis

Type

  • Home
3 Bedrooms
2 Baths
5 Guests
Welcome to a golfer’s paradise at Spa Oasis!

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.

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