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 33

GOLF COURSE 3 Bed Home - Monthly Glenwood Canyon 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 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.



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!



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

HELICONIA HOUSE (monthly rental): 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 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 2 Bed Home - Monthly Key West, FL 2 bedrooms
2.5 baths
 

GREEN ORCHID (monthly rental): 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 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 the beach, airport and favorite local haunts.  2 bedrooms, 1.5 bath, freshly painted, new appliances -- a home away from home.  Located in the exclusive Key West Golf Club; close to Old Town when you want it, far enough away when you don't.



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...



GOLF COURSE 2 Bed Home - Monthly Glenwood Canyon 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.



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
 

TRES GATOS (monthly rental): Spend a month in one of Key West's revered neighborhoods;  live like a local in this 2-bedroom Conch cottage. Close to Higgs Beach, Sandy's Cafe and our infamous local grocery, Fausto's Food Palace.  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 Condo - Monthly Key West, FL 2 bedrooms
2 baths
 

HIDDEN TREASURE (monthly rental): 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.



GOLF COURSE 2 Bed Home - Monthly Glenwood Canyon 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 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 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.



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.



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

ECCO DOMANI (monthly rental):  Meaning "Here Tomorrow", a beautiful 3 story home with private pool and attractive appointments -- your 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.



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

A SUITE PARADISE (monthly rental) : This lovely 3 bedroom 2 bath home 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.



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

CONCH CABANA (monthly rental): 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 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.



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

SEASIDE ESCAPE (monthly rental): 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.



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Showing homes 1 - 25 of 33