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 13 rentals matching your search criteria
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Papa's Cottage Retreat

Type

  • House
Old Town
1 Bedroom
1 Bath
2 Guests

As you step through the natural wooden gate onto the brick pathway, you will be embraced by this private garden oasis.

Ibis

Type

  • Cottage
Old Town
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 with a shared pool on property.

A Little Slice Of Paradise

Type

  • Townhouse
Stock Island
2 Bedrooms
1.5 Baths
5 Guests

Located on the main road meandering through the secluded gated Key West Golf Club community, you’ll find A Little Slice of Paradise. Spend a month (or two) in this charming townhouse and you may never return home.

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!

Southard Square Hideaway

Type

  • Condominium
Old Town
1 Bedroom
1 Bath
4 Guests

A quiet oasis in Old Town Key West that offers a beautiful shared pool and off street parking.

Perfect Pineapple

Type

  • House
Old Town
2 Bedrooms
1 Bath
4 Guests

Long considered a sign of hospitality, the pineapple is widely recognized as sign of Welcome and Friendship, and so we welcome YOU to the Perfect Pineapple!

Ecco Domani

Type

  • House
Old Town
3 Bedrooms
2.5 Baths
6 Guests

A beautiful three-story home with private pool, off street parking, and attractive decor, Ecco Domani is a wonderful Key West escape that you will want to come home to year after year.

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.

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.

Casa de Rosalie

Type

  • House
Old Town
3 Bedrooms
2 Baths
8 Guests

Built in 1889 with original Dade County Pine, history comes alive when you enter this luxurious private home.

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.

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.

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