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 13 - 24 of 36 rentals matching your search criteria
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Coconut Cottage

Type

  • Cottage
Old Town
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.

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!

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 tune into the Windchime!

Emma's Escape

Type

  • Condominium
Old Town
2 Bedrooms
1 Bath
4 Guests

Lounge your days away by the pool or enjoy the peace and quiet away from the hustle and bustle of Duval Street.

Lighthouse Villa

Type

  • House
Old Town
3 Bedrooms
4.5 Baths
8 Guests

Amid the most iconic historic sites in Key West you’ll find the Lighthouse Villa, a timeless and private Conch home.

Under The Palms

Type

  • House
Mid Town
2 Bedrooms
2 Baths
4 Guests

Meander down a quiet street in midtown Key West until you come upon a white picket fence on a shady corner lot. Park and walk around to open the gate.

Bogey's Retreat

Type

  • Townhouse
Stock Island
2 Bedrooms
1.5 Baths
4 Guests

Additional outdoor space on your wrap around porch and large bricked patio to enjoy the tropical breezes.

Coral Breeze

Type

  • Townhouse
Stock Island
2 Bedrooms
1.5 Baths
4 Guests

For the golfer in the family and for those who just want an idyllic vacation spot, Coral Breeze is the perfect choice!

Coral Garden

Type

  • Townhouse
Stock Island
2 Bedrooms
2.5 Baths
4 Guests

For those looking for a cozy little getaway on a budget - Coral Garden is the answer!

Spa Oasis

Type

  • House
Stock Island
3 Bedrooms
2 Baths
6 Guests

Welcome to a golfer’s paradise at Spa Oasis!

Sunny View

Type

  • Cottage
Old Town
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.

Conch Republic Retreat

Type

  • Cottage
Old Town
2 Bedrooms
2 Baths
4 Guests

Located in the quiet neighborhood of The Meadows, you’ll find the Conch Republic Retreat, a quintessential cigar maker’s shotgun style house, circa 1890.

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