Key West Monthly Vacation Rentals

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 pure white 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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Showing homes 1 - 25 of 34

OLD TOWN 3 Bed Home - Monthly Key West, FL 3 bedrooms
2.5 baths
 

HELICONIA HOUSE: Beautiful and exotic as the plant itself, Heliconia House is an exceptional example of luxurious living in its simplest form. This pristine 3 bedroom 2.5 bath home with private pool is stocked with everything you'll ever need, nestled in one of Key West's historic neighborhoods.  Walk to anywhere you want to be on our island Paradise.



OLD TOWN 3 Bed Home - Monthly Key West, FL 3 bedrooms
2.5 baths
 

FAN-tastic GETAWAY (monthly rental): This home has everything, including a bit of Key West history. Formerly owned by actress and fan dancer, Sally Rand, this spacious, fully renovated 3-bedroom, 2.5 bath home in the Old Town neighborhood known as The Meadows, with luxurious pool, chef's kitchen and outdoor great room.



OLD TOWN 2 Bed Home - Monthly Key West, FL 2 bedrooms
2 baths
 

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!



GOLF COURSE 2 Bed Condo - Monthly Key West, FL 2 bedrooms
1.5 baths
 

LAKEVIEW (monthly rental): Come to Key West where the sun always shines!! Stay in a beautiful 2 bedroom 1.5 bath bungalow in the gated Key West Golf Club community. Stroll the lushly landscaped grounds, relax in the pool, play a round of golf, and when you venture out, you will be close to it all - beaches, downtown and some of our favorite local restaurants.



GOLF COURSE 2 Bed Home - Monthly Key West, FL 2 bedrooms
1.5 baths
 

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.  



OLD TOWN 2 Bed Home - Monthly Key West, FL 2 bedrooms
2 baths
 

REJUVENATE!!! (monthly rental): This is a Key West experience you don't often find. This spacious 2-bedroom 2-bath cottage with extra large kitchen opens to a private lanai with heated jacuzzi.  You'll find more reason to be outside than inside!  Add to it the pleasure of sharing  pool and jacuzzi (not heated) with other homes in this intimate compound and you'll have everything you need.



OLD TOWN 1 Bed Home - Monthly Key West, FL 1 bedroom
1 bath
 

IBIS (monthly rental): Ibis is a wonderful 1 bedroom 1 bath home that shares the pool and laundry facilities in The Colony Suites compound. Just a couple of blocks to Duval Street, walking distance to restaurants, shopping and attractions of Old Town Key West. Live like a local and find out why we call Key West our island paradise.



OLD TOWN 2 Bed Home - Monthly Key West, FL 2 bedrooms
1 bath
 

SUNNY DAYS (monthly rental): Beautifully maintained while retaining its original style and structure, this quaint 2 bedroom 1 bath cottage has Dade County pine throughout the property adding a feel of old Key West. The furnishings are tasteful and comfortable, the neighbors in this intimate compound are friendly and the pool and jacuzzi are inviting.



OLD TOWN 1 Bed Home - Monthly Key West, FL 1 bedroom
1 bath
 

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.



OCEAN SIDE 2 Bed Condo - Monthly Key West, FL 2 bedrooms
2 baths
 

SEASIDE ESCAPE: The name says it all. Stay for a month at Seaside Escape and enjoy the ocean views, balmy breezes and casual lifestyle that is the essence of Key West living.  This condo is sure to delight your family and friends, enticing you to return again and again.



GOLF COURSE 2 Bed Home - Monthly Key West, FL 2 bedrooms
1.5 baths
 

WIND SWEPT (monthly rental): Imagine yourself nestled within a serene, lushly landscaped picturesque community with walkways meandering around the only Caribbean golf course in the United States.  This lovely 2 bedroom 1.5 bath townhome is tastefully furnished with a well-stocked kitchen and located a few doors from the community pool.



OLD TOWN 2 Bed Home - Monthly Key West, FL 2 bedrooms
1 bath
 

TRES GATOS (monthly rental): Spend a month in one of Key West's revered neighborhoods;  live like a local in this sweet 2-bedroom Conch cottage. Close to Higgs Beach, Sandy's Cafe and our infamous gourmet grocery, Fausto's Food Palace; a quick bike ride to Duval Street. Take a sunrise swim in your pool, pick up a con leche from Sandy's and your day has started in the right direction.



OLD TOWN 2 Bed Home - Monthly Key West, FL 2 bedrooms
2 baths
 

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.



OLD TOWN 2 Bed Home - Monthly Key West, FL 2 bedrooms
2 baths
 

KEY LIME PIE (monthly rental): A little slice of paradise located one block from the Historic Seaport on a tiny lane. Close enough to bike to all the sights and attractions of Old Town; far enough away to forget you are staying right in the middle of the action. 2 bedrooms 2 baths with private swim spa, this home will give you a reason to say, Ahhh...



MID TOWN 2 Bed Condo - Monthly Key West, FL 2 bedrooms
2 baths
 

BOATER'S BEACH HAVEN (monthly rental): A truly unique Key West vacation location. Located midtown on Florida Bay, you'll have first row seats for sunset every night. Take advantage of the private boat dock with your own or a Key West boat rental.  A quick bike ride will get you to Old Town, but you may never want to leave home.



OLD TOWN 2 Bed Home - Monthly Key West, FL 2 bedrooms
2 baths
 

EXHALE (monthly rental): Located on a quiet tree lined street in the heart of Old Town, you will enter into a a tropical escape surrounded by sunshine, ocean breezes and EXHALE. A quaint cottage with the true spirit of Key West combining indoor and outdoor living into one. Walking or biking distance to anything you will want to do while enjoying the lifestyle of a local.



OLD TOWN 1 Bed Home - Monthly Key West, FL 1 bedroom
1 bath
 

CASITA de CATHERINE (monthly rental): Come stay and play in this cozy cottage only steps away from Duval Street! Sunny days and tropical breezes are guaranteed; it’s the perfect place to relax, rejuvenate, and relish all the greatness you came to expect for your stay in Key West. 1 bedroom with king bed, queen sleeper sofa, private deck with jacuzzi, all the comforts of home, and more.



MID TOWN 2 Bed Home - Monthly Key West, FL 2 bedrooms
2 baths
 

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.



OLD TOWN 1 Bed Home - Monthly Key West, FL 1 bedroom
2 baths
 

SUNNY VIEW (monthly rental): Adorable, affordable, and a great location! Sunny View is the perfect escape for a couple looking to get away from it all in Paradise. A sweet 1 bedroom cottage with bricked backyard, a perfect spot for your morning cafe con leche. Convenient to downtown and shopping. Live like a local on Key West time.



OLD TOWN 2 Bed Home - Monthly Key West, FL 2 bedrooms
2 baths
 

CONCH ESCAPE (monthly rental): 2 bedroom 2 bath cottage in a quiet Old Town neighborhood, this property has a renovated kitchen and other recent updates making it comfortable and inviting. Enjoy a cocktail on the private deck in your own backyard, or stroll over the the pool shared by an intimate group of neighbors.



MID TOWN 2 Bed Home - Monthly Key West, FL 2 bedrooms
3 baths
 

CAYO HUESO SUNSHINE (monthly rental): A brand new 2-bedroom 3-bath home with den in a new Key West neighborhood -- quiet and secluded yet so accessible to the wonders of our island.  A block from Higgs Beach on the Atlantic Ocean, one of the best locations you'll find, with lots of extras to make you want to return again and again.



OLD TOWN 2 Bed Condo - Monthly Key West, FL 2 bedrooms
1 bath
 

EMMA'S SECRET (monthly rental):  Luxurious 2 bedroom 1 bath condominium located in the historic Bahama Village neighborhood of Old Town offers all the amenities of home.  Enjoy the tropical backyard ambience with jacuzzi, pool and tiki hut.   Located in walking distance to Duval Street, the heart of Key West with all the activities, restaurants, speciality shops and nightlife.



OLD TOWN 3 Bed Home - Monthly Key West, FL 3 bedrooms
2.5 baths
 

ECCO DOMANI (monthly rental):  Meaning "Here Tomorrow" this is a beautiful 3 story home with private pool, off street parking and attractive appointments -- a wonderful Key West escape.  Tucked away in a quiet spot in Old Town yet only one block from the action on Duval Street.  Dream the day away in your own private sanctuary; spend the evening taking in all Old Town Key West has to offer.



GOLF COURSE 2 Bed Home - Monthly Glenwood Canyon 2 bedrooms
3 baths
 

CASA FLORA (monthly rental): This lovely home overlooks the greens at the Key West Golf Club. On the first floor you will find the kitchen, dining area, living room, den with sleeper sofa and a full bath. Upstairs are 2 bedrooms with baths ensuite. Relax in the luxury of your own backyard with private pool or take a stroll through the lushly landscaped grounds of this gated community.  



GOLF COURSE 3 Bed Home - Monthly Key West, FL 3 bedrooms
3 baths
 

SUNSET LAKE (monthly rental): Discover Paradise and leave your worries back home. This 3 bedroom 3 bath townhome exudes an ambiance of peace and tranquility. Located in the exclusive gated community, Key West Golf Club, you can stroll the grounds, sun at the pool, play a round of golf, or sit on your porch watching the local wildlife congregate at the lake.



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Showing homes 1 - 25 of 34