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 34 rentals matching your search criteria
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Cottage by the Pool

Type

  • Townhouse
Stock Island
2 Bedrooms
1.5 Baths
4 Guests

In this cozy home you will find yourself nestled in the center of the Key West Golf Club on a secluded lane that cuts through the heart of its community.

La Casita

Type

  • House
Old Town
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.

Treetop Paradise

Type

  • Condominium
Old Town
2 Bedrooms
2 Baths
4 Guests

Located in the historic Bahama Village neighborhood, nestled amongst the palms, you‘ll find the stately building that houses Treetop Paradise.

Paradise Palms

Type

  • House
Old Town
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!

Emma's Secret

Type

  • Condominium
Old Town
2 Bedrooms
1 Bath
4 Guests

Located in one of Key West’s historic and most cultural neighborhoods this lovely condominium will give you cause to celebrate the island way of life.

Flagler's Oasis

Type

  • House
Mid Town
2 Bedrooms
1 Bath
4 Guests

Bask in complete privacy in this Key West tropical paradise with a lagoon style pool. This property is pet friendly.

Flagler Station

Type

  • House
Mid Town
3 Bedrooms
2 Baths
6 Guests

With family in mind, this lovely 3 bed, 2 bath private home has plenty to offer with a private outdoor pool and patio space. Spend your days enjoying paradise in this spacious monthly rental. This one is a priceless gem!

Key Lime Pie

Type

  • Cottage
Old Town
2 Bedrooms
2 Baths
4 Guests

Key Lime Pie is the private cottage that perfectly encompasses the “Key West vibe” that you’re looking for. The minute you walk in to see the bright, sunny walls and local artwork, you know you are somewhere special.

Lazy Gecko

Type

  • Condominium
Old Town
2 Bedrooms
1.5 Baths
4 Guests

Grab your bike and head for some fresh seafood at the Historic Seaport. Walk four blocks to bustling Duval Street to find the perfect t-shirt or enjoy a cold brew and people watch at a street view table.

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.

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!

First Breath

Type

  • House
Old Town
3 Bedrooms
2 Baths
6 Guests

Bring the family to this 3 bed, 2 bath private conch home and enjoy your large private pool and outdoor area as the days pass by.

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