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 36 rentals matching your search criteria
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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.

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 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!

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.

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.

Newton's Nest

Type

  • Condominium
Old Town
1 Bedroom
1 Bath
2 Guests

Newton's Nest is a quiet little refuge tucked away in Old Town where you can set up roost, stay for a month or more and enjoy a leisurely existence.

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.

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.

Coral Villa

Type

  • Townhouse
Stock Island
3 Bedrooms
3 Baths
6 Guests

This charming, clean and nicely decorated vacation rental home is located in Coral Hammock, one of Key West newest communities, very close to restaurants, boating and water adventure!

Boat House

Type

  • Cottage
Old Town
1 Bedroom
2 Baths
2 Guests

Step into a tranquil community on a quiet lane and discover the Boat House, a nautically themed treasure in Old Town Key West.

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.

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