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 35

OLD TOWN Key West, FL 2 bedrooms
2.5 baths
 

DUVAL ON THE SQUARE (monthly rental):  Located at the Duval Square townhomes directly on Duval but above all the hubbub. The townhomes are built on the second and third story of the complex with community pool overlooking Duval Street. This lovely 2 bedroom 2.5 bath townhome is available for a relaxing, luxurious month in Paradise.



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.



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

CONCH CABANA: Check into Conch Cabana and leave your worries behind. Simple yet so comfortable for just the two of you in this lovely historic Conch studio cottage.  Centrally located in Old Town, just steps from Ernest Hemingway's home and the Lighthouse Museum, one block from Duval and a quick bike ride to the beach.  Everything you want is here waiting for you.



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 bath
 

AQUA (monthly rental): What comes to mind when you think of the color aqua? This home was lovingly designed to give you that sense of peace and serenity, balmy breezes and crystal clear waters.  Located within the gated community of the Key West Golf Club with clubhouse, pool and meandering walkways to view local fauna and flora.



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

ATLANTIC BLUES (monthly rental):   A stylish example of Conch architecture, this 2 bedroom 1 bath cottage has been totally renovated with hardwood floors, beautiful glass tiles, shining granite countertops, top notch kitchen appliances and décor that is playful and soothing. Add the luxury of your own dipping pool and you know you have found your home.



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

ROBIN'S ROOST: Tucked away in a quiet local neighborhood, Robin's Roost sits pretty in its own little world. Step through the front entry into an open living space that leads to its private yard with jacuzzi to soothe your cares away.  Located in Old Town in walking/biking distance of everything Key West has to offer.



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

A SLICE OF PARADISE (monthly rental): Imagine life in a secluded, golf community, minutes from beach, airport and local's favorite restaurants.  Two bedrooms, 1.5 bath, freshly painted, new appliances and eager to offer you a home away from home.  Located on the main thoroughfare of the exclusive Key West Golf Club, close enough to Old Town when you want it, far enough away when you don't.



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.



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
1 bath
 

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.



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

EMMA'S ESCAPE (monthly rental): Beautiful and spacious 2 bedroom 1 bath ground-level condo located in historic Old Town's Bahama Village neighborhood. Emma’s Escape is one of four condos that share the large landscaped backyard, complete with jacuzzi, pool and tiki hut. Live like a local and you will know why we call it Paradise.



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 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 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 2 Bed Home - Monthly Key West, FL 2 bedrooms
2.5 baths
 

GREEN ORCHID: Dreaming of living like a local in Key West? Dream no more. Green Orchid offers a true Conch experience situated on a narrow lane in one of the last historic Old Town neighborhoods.  Inside you'll live with all the modern conveniences and furnishings; outside you'll feel you've been transported to years gone by.



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

ISLAND BREEZE (monthly rental): Located in the exclusive Sanctuary within the Key West Golf Club, this spacious home allows for lots of visitors with 3 bedrooms plus a sleeper sofa. Enjoy the quiet solitude of this secure gated community. And when you're ready for the chaotic activity of Duval Street, you are a quick 10-minute drive away.



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.



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.  



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.



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 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
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.



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Showing homes 1 - 25 of 35