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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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.

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.

Tradewinds

Type

  • Condominium
Ocean Side
3 Bedrooms
2 Baths
6 Guests

A quick jaunt across the street takes you to Key West’s longest beach. A few blocks away you’ll discover dining and shopping galore on famous Duval Street. A short bike ride and you're at the Historic Seaport.

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.

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.

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.

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.

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.

Bye Bye Birdie

Type

  • Townhouse
Stock Island
3 Bedrooms
2 Baths
6 Guests

Find serenity in this pleasant and spacious home with tons of Key West charm. Featuring an abundance of back yard space for lounging or entertaining, you will not want to leave this lovely retreat.

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!

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