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.

Your search has found 35 homes
Homes per page:
1 2 Next
Showing homes 1 - 25 of 35

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.



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.



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 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 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.



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
 

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 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.



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.



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
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
2.5 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.



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
 

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...



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 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!



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
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.



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.



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
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.



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 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.



1 2 Next
Showing homes 1 - 25 of 35