Key West Vacation Rentals in FL with Free Concierge Service

CORAL SUITE: If you're looking for a home away from home that will leave you with money in your pocket, Coral Suite is the place for you. This 2 bedroom 2.5 bath townhome in the gated community of Coral Hammock has all the comforts including flatscreen TVs, washer/dryer, private parking, WIFI, and convenient to some of our local favorite restaurants, beach and airport.

ALLURING PORCHES: A beautiful 2 bedroom 3 bath townhome with den, offering 3 private bedrooms with baths ensuite. Enjoy the abundant french doors that open the entire downstairs to the outdoors and give this home easy open air living. Located in the Porter Lane section of Truman Annex in walking distance of all there is to enjoy in Old Town.

KEY WEST GINGER HOUSE: An absolute jewel a few doors from Duval Street, this single family home is named for the breathtaking ginger plants blooming in our tropical paradise. Featuring 2 bedrooms and 2 full baths with a private jacuzzi in the garden. Soothe your muscles after a full day of partying downtown.

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.

THE HEMINGWAY: A beautiful 2 bedroom 2 bath townhome located in the private, gated community of Truman Annex. Just steps away from the community pool and only 2 blocks from famous Duval Street and historic Old Town Key West. Relax on your back porch, take a dip in the pool, and check out the sights that you have heard so much about on our Island paradise.

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.

PARADISE PLACE: This ground-level 1 bedroom 1 bath condominium located in the Palm Gardens community is in the heart of the Art district and just 6 blocks from Duval Street and the Historic Seaport. Soak up the sun in the relaxing swim spa or bike down to Duval Street to be a part of the action. You can have it all!

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.

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.

CARIBBEAN DUVAL:  Nestled above Duval Street in the heart of the Art district, this lovely 2 bedroom, 2.5 bath townhouse, a spacious 1,300 sq. ft. hideaway, features central A/C and an open floor plan with a half bath on the first floor and a full bath in each bedroom upstairs. Duval Square, a gated, secure rooftop community with pool is centrally located in Old Town Key West.

FINN KEY:   Beautiful 2 bedroom 1 bath downstairs condominium with all the modern conveniences located in Truman Annex, steps away from the community pool and walking distance to Fort Taylor State Park for beach and sunset views.   Just 2 blocks from Duval Street and the attractions of historic Old Town Key West.  Everything you're looking for within easy reach.

BAHAMIAN REED: A luxury 2-bedroom 1.5 bath townhome located in the prestigious gated community of Truman Annex in walking distance of all the activities in Old Town Key West -- Fort Zachary Taylor State Park and beach, Duval Street and the nightly Sunset Celebration at Mallory Square, shopping, bars and restaurants.

TROPICAL DREAMING: This tropical 2-bedroom home with sleeper sofa offers all the comforts of home. There are classic art features, hardwood floors, tall ceilings, and a true Key West feel. Sip a con leche on the back deck in the morning, swim and sun in the afternoon in your private pool, then head 1 block to Duval Street for the eclectic nightlife. It does not get better than this!

SOUTHERN WIND: A renovated 2 bedroom 2 bath 2-story home located in the Windward Park compound in the heart of Old Town, 1 block from Duval Street and walking distance to the sights and attractions of the Historic district. This home is equipped with all the comforts of home and more. Nestled in the far corner of the compound adds privacy to this home away from home.

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.  

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.

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.

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.

DUVAL BREEZE:  Enjoy the great location of  this beautiful 2 bedroom 2.5 bath townhome located in the gated rooftop community of Duval Square. This great location is steps away from fantastic restaurants, nightlife, bars and shopping on Duval Street in Old Town Key West.  Check out chaotic Duval Street, then relax  on your private balcony.  Ahhh...

FLORIDA PALM: 2 bedroom 2 bath condominium with sleeper sofa offers your family the peace and tranquility you want while home, within minutes of the hectic lifestyle of downtown. Condo complex offer jacuzzi, pool, BBQ and tennis courts for your vacation pleasure. Located next to Smathers Beach where you can walk to promenade on the Atlantic Ocean witnessing magnificent sunrise.

OSPREY: This quaint cottage is located in The Colony Suites, a charming and secluded Key West style compound nestled in the heart of historic Old Town Key West, just 2 blocks from Duval Street. Compact and well-appointed, it is perfect for two people who want to relax, swim and walk around Duval Street, day after day.

BEACH HOUSE CONDO:   A beautiful 2 bedroom 2 bath Shipyard condominium with private jacuzzi, located in the prestigious Truman Annex community. This gated community in Old Town Key West is ideal -- only 2 blocks from bars, restaurants and shopping on famous Duval Street and walking distance to all of the attractions you came here to see.

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.

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.

AMELIA HOME:  A private Key West vacation home that is only four blocks from one of our most popular beaches on the Atlantic Ocean and one block from all the Duval Street entertainment.  This 2 bedroom 2.5 bath single family home with private pool is located in one of the most interesting neighborhoods in the historic district of Old Town Key West.