Key West Vacation Rentals

Find Monthly Vacation Rentals In Key West, Florida

Key West vacation homes in Florida, like the ones offered by At Home Key West, have been adored by all who set foot on our sands. Harry S. Truman spent his winter down here, and Ernest Hemingway called the island his home for many years. At Home Key West is proud to offer monthly vacation homes for guests who want to take full advantage of our beaches and radiant blue ocean. 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

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2 Bedrooms
2½ Baths
Sleeps 6
Type of property: Condo
Area: Mid Town

Sunshine On The Rocks (Monthly Rental) 
A true island getaway! This stunning townhome has spectacular waterfront views of the bay, travel down to Key West by boat or bring it along because this is one of the only places on the island with open water boat dockage. Sunshine On The Rocks is the hideaway you are looking for when tropical breezes call your name and turquoise waters is where you are heading.


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2 Bedrooms
2½ Baths
Sleeps 4
Type of property: Townhouse

THE GALLERY - This is a very unique home where the original owner has kept this little treasure all to herself and now wants to share it with you!  An accomplished artist, the home is filled with her original artwork of favorite things in Key West.  Excellent location in Key West Golf Club with the community pool just outside the back steps with easy access to the clubhouse and library.


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2 Bedrooms
2 Baths
Sleeps 6
Type of property: Cottage
Area: Old Town

NAUTICAL DREAMS (monthly rental): Here's the perfect spot for whatever you desire, parties or peace & quiet. This 2 bedroom 2 bath home, in a small compound of 8 cottages, opens from each bedroom and the living room onto a grand private deck with ample space for entertaining or relaxing with a book. Walking through this well-established local neighborhood is an added bonus.


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1 Bedroom
2 Baths
Sleeps 2
Type of property: Cottage
Area: Old Town

COCONUT COTTAGE (monthly rental): Adorable, affordable, and near all the action?.... you bet! Coconut Cottage is the perfect escape for a couple or singles looking to get away from it all in paradise… Located in a quiet neighborhood of Old Town Key West, this 1 bedroom 2 bath cottage is a gorgeous spot to rest your head in our island city.


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3 Bedrooms
2 Baths
Sleeps 6
Type of property: Luxury
Area: Mid Town

A SUITE PARADISE (monthly rental) : This lovely 2 bedroom 2 bath home with den is truly a tropical hideaway tucked away in a secluded Key West neighborhood, yet minutes from all the Duval Street entertainment and Historic Seaport. You can relax and be pampered in a superbly appointed and decorated private home that has every amenity you could desire.


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1 Bedroom
1 Bath
Sleeps 4
Type of property: Cottage
Area: Old Town

VARELA COTTAGE (monthly rental): A true Conch cutie snuggled in Old Town. Varela Cottage is a 1 bedroom 1 bath cottage with an additional sleeping area in the loft. Located in a well-established local neighborhood, the open-floor plan of this home and private jacuzzi in the lushly landscaped backyard beckon you to our Island paradise.


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2 Bedrooms
1½ Baths
Sleeps 4
Type of property: Townhouse
Area: Stock Island

BOGEY'S RETREAT (monthly rental): Welcome to Bogey's Retreat, your home away from home in Key West. This lovely townhome is located in the exclusive Golf Course community, and allows you to enjoy everything Key West has to offer in a relaxing environment.  New to the rental market and updated from top to bottom with supreme comfort in mind.  


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1 Bedroom
2 Baths
Sleeps 2
Type of property: Private Home
Area: Old Town

TROPICAL CASITA: It is rare you find a true jewel like Tropical Casita, nestled in a sweet little spot amid lush landscaping and secluded tranquility.  Languish in the grandiose bedroom on the second level, unwind around the pool, dine under the stars and sunbathe on the private upper level deck.  Decadence at its best.


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2 Bedrooms
2 Baths
Sleeps 4
Type of property: Townhouse
Area: Old Town

Shrimp Party (MONTHLY RENTAL) Key West Pinks, Parties and Drinks, that is the theme for this island retreat, Shrimp Party! When you think that a quick getaway pack your gear and settle in for a month or longer.


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3 Bedrooms
2 Baths
Sleeps 8
Type of property: Private Home
Area: Mid Town

FLAGLER STATION (monthly rental): This one just arrived and it is a true gem! Flagler Station was just remodeled, refurbished and re-furnished. High speed WIFI and state-of-the-art electronics, top-of the-line gourmet kitchen and luxury linens make this home the one you'll return to year after year.


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2 Bedrooms
2½ Baths
Sleeps 4
Type of property: Townhouse
Area: Stock Island

KOKOMO (monthly rental): Everybody knows a little place like Kokomo. Now if you want to go and get away from it all go down to Kokomo. Tropical drinks melting in your hand, we'll be falling in love to the rhythm of a steel drum band down in Kokomo.  Located in the exclusive Key West Golf Club Community you will enjoy a beautifully manicured landscaped grounds, a fabulous pool with waterfall and access to the fitness facility.


Call For Availability and Pricing
2 Bedrooms
2½ Baths
Sleeps 4
Type of property: Private Home
Area: Old Town

VERANDAH (monthly rental): Tucked away on Frances Street lies your island escape called Verandah, named for the lanai surrounded by Bahama shutters allowing tropical breezes to waft through. A stunning 2 bedroom 2 bath home with private pool in a quiet residential neighborhood with plenty of space for your family to stay and play!


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2 Bedrooms
1 Bath
Sleeps 4
Type of property: Private Home
Area: Old Town

PERFECT PINEAPPLE (monthly rental): Long considered a sign of hospitality, the pineapple is now widely recognized as a sign of Welcome and Friendship...and so we welcome you to the Perfect Pineapple. This quaint Conch cottage, 2 bedrooms 1 bath has all the amenities for your visit, including a side yard where you can sunbathe, swim and BBQ to your heart's content.


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2 Bedrooms
1 Bath
Sleeps 3
Type of property: Cottage
Area: Old Town

William's Loft (Monthly Rental)
Located in Old Town in a small, quiet compound of cottages sits William's Loft in one of Key West's most desirable neighborhoods. A secluded compound surrounded by lush tropical foliage make this the idyllic escape. The cottage is exactly as you envision in Key West with distressed wood floors and Dade County Pine plus all the modern amenities of home.


Call For Availability and Pricing
2 Bedrooms
2 Baths
Sleeps 4
Type of property: Condo
Area: Old Town

HIDDEN TREASURE (one of our monthly vacation rentals): You could easily pass by this jewel of a home without ever knowing it was there. Located down Wong Song Alley behind a private fence, a few steps past the pool and you've reached your sanctuary. Fresh paint and new furnishings in this sweet space, Old Town living for a song and a dance, discover this hidden treasure for yourself.


 

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