Key West Monthly Vacation Rentals

JOSEPHINE (monthly rental): Tastefully furnished 2 bedroom 2 bath private single family home in the center of the island, one block from Smathers Beach along the Atlantic Ocean. This property features a swimming pool surrounded by a deck, beautiful landscaping and privacy fencing. Live like a true local in this quiet, residential neighborhood.

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.

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.  

BIRD'S NEST (monthly rental): Come to Key West, where the sun always shines! Stay in a beautiful 2 bedroom 2.5 bath townhome in the gated Key West Golf Club community. Stroll in quiet solitude through the manicured grounds, relax by the pool, play a round of golf. You're close to it all - beaches, downtown, the airport and some of Key West locals' favorite bars/restaurants.

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.

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...

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 den off the living room with 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.

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.

CORNER PLACE (monthly rental): Come to Key West where the sun always shines! Stay in a beautiful 2 bedroom 1 bath home in the gated Key West Golf Club community where you can stroll through lushly landscaped grounds, relax at the pool, tone up in the fitness center, or sip a cocktail on your screened porch, thankful to be in Paradise.

CASA LAGUNA (monthly rental): Spacious accommodations with 3 bedrooms 3 bathrooms plus den in a private home located at the Key West Golf Club. This home offers fantastic views to sit and relax, watch the golfers and enjoy peace and solitude. When you crave some action, the beach and some of our finest local restaurants are minutes away.

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.

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.

ATLANTIC BLUES (monthly rental):   A stylish example of Conch architecture, this 1 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.

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.

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.

ISLA PARAISO (monthly rental): This home was specially designed to the owner's requirements. Stunning 3 bedroom 3.5 bath home with private pool overlooking the Gulf of Mexico with a perfect view of sunset -- every night! Located two miles from downtown; convenient to all major shopping centers on the island.

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.

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.

TEE TIME (monthly rental): Come to Key West, where the sun always shines! Stay in a beautiful 3 bedroom 3 bath Conch-style home in the gated Key West Golf Club community and you will be close to it all - pools and golf course a few steps away, beach, airport and downtown a few minutes away. You could not ask for more.

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.

SOUTHERN COMFORT (monthly rental): Best of both worlds! Stay in a beautiful 2 bedroom 2.5 bath Conch-style home in the peaceful, gated Key West Golf Club community -- stroll the lushly landscaped grounds, take a swim, play some golf. Head out to some of our favorite local restaurants and marinas just across the road or to downtown Key West, 5 minutes farther down the road.

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.

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 loft, private deck with jacuzzi, all the comforts of home, and more.

EDEN ON EATON: You can have the best of both worlds, right here and now. Live in a historic Conch cottage with subtle details of days gone by, located in the middle of the action on Eaton Street in Old Town Key West. A quick walk or bike ride to the historic seaport, bars, restaurants, shops. Relax on the private deck or sip a cocktail on the front porch watching the people pass by.

SUNDOWN COTTAGE (monthly rental): Enjoy peaceful solitude in this 3 bedroom 2 bath home in the Key West Golf Club community with front row seats of golfers meandering around the course right in front of you. If you get tired of swimming in the community pool or golfing on the beautifully designed greens, take a 5minute drive to Old Town to check out the sights.