WiFi Access | Luxury Key West Vacation Rentals
Vacation houses in Key West can be chosen by category and or amenity
| TRUMAN ANNEX | 2 Bedroom Condo | Key West, FL | 2 bedrooms 2 baths |
$1,300 - $2,791 |
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.
| 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 |
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.
| MID TOWN | 3 Bed Home - Monthly | Key West, FL | 4 bedrooms 3.5 baths |
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.
| OLD TOWN | 2 Bedroom Condo | Key West, Fl | 2 bedrooms 2.5 baths |
$225 - $2,719 |
DUVAL SEA TURTLE: This 2 bedroom 2.5 bath townhome with sleeper sofa offers comfort and space for a family of six. Conveniently located in the rooftop townhome community of Duval Square, you\\'re close enough to the eclectic activity of Duval Street, and far enough to enjoy peace and quiet in the privacy of your own home.
| TRUMAN ANNEX | 2 Bedroom Condo | Key West, FL | 2 bedrooms 1 bath |
$1,100 - $2,538 |
LAVENDER JUNGLE: Beautiful 2 bedroom 1 bath downstairs Shipyard condo in Truman Annex with back deck that opens to the entrance of Fort Zachary Taylor State Park, one of the nicest beaches on the island. Truman Annex, a secure gated community within Old Town Key West, is within walking distance of all the favorite hotspots on the island.
| OLD TOWN | 3 Bedroom Home | Key West, FL | 3 bedrooms 3.5 baths |
$595 - $8,075 |
BAHAMA HOUSE: Location, location, location! New and totally gorgeous, this spacious house is conveniently located on a quiet street in the heart of Old Town Key West only half a block from the fabulous shops, activities, restaurants and nightlife on Duval Street. Lounge at the pool in total privacy and solitude by day; take the walk around the corner to experience Key West nightlife.
| TRUMAN ANNEX | 2 Bedroom Condo | Key West, Fl | 2 bedrooms 1.5 baths |
$1,300 - $2,864 |
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.
| OLD TOWN | Key West, FL | 2 bedrooms 2.5 baths |
DUVAL ON THE SQUARE - 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 2 baths |
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.
| OLD TOWN | 1 Bedroom Home | Key West, FL | 1 bedroom 1.5 baths |
$190 - $2,248 |
TRANQUILITY: This charming split level cottage offers 1 bedroom 1 full bath upstairs with sleeper sofa and half-bath downstairs. Cozy furnishings, soothing colors and modern conveniences make this the perfect spot for your visit to Key West. Stay in the heart of Old Town and walk to all there is to see on our island Paradise.
| OCEAN SIDE | 2 Bedroom Condo | Key West, FL | 2 bedrooms 2 baths |
$345 - $3,369 |
KEY WEST CROWN JEWEL: We know that you will enjoy staying in our little bit of Paradise. This is a 2 bedroom, 2 bath Penthouse condominium with 1350 square feet of living space. Located on the Atlantic Ocean with magnificent views from every room. A short bike ride downtown and you are in the midst of what has made Duval Street infamous: bars, restaurants, and galleries galore.
| OCEAN SIDE | 3 Bedroom Condo | Key West, FL | 3 bedrooms 2 baths |
$375 - $4,344 |
SURF SIDE - Search no further! This fabulous condominium is directly on the Atlantic Ocean. Located at the end of the building closest to the beach, the balcony wraps around offering full ocean views from the 3 bedrooms and the living room. Stylish furnishings, well-equipped kitchen and all the modern conveniences are here for your pleasure.
| 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.
| GOLF COURSE | 2 Bed Condo - Monthly | Key West, FL | 2 bedrooms 1 bath |
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.
| OLD TOWN | Studio Condo | Key West, FL | 1 bedroom 1 bath |
$120 - $1,740 |
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.
| OLD TOWN | 3 Bedroom Home | Key West, FL | 3 bedrooms 2.5 baths |
$625 - $9,063 |
DUVAL PENTHOUSE: A large luxury apartment located in downtown Key West with rooftop views of Duval Street. This property has it all, fabulous location, beautiful furnishings and plenty of space to accommodate your friends and family. 3 bedrooms 3 bath on the 2nd and 3rd levels, with pool on the ground level. Very chic and urban modern in our laid back island paradise.
| OLD TOWN | 2 Bed Home - Monthly | Key West, FL | 2 bedrooms 2 baths |
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.
| OLD TOWN | 2 Bed Home - Monthly | Key West, FL | 2 bedrooms 2.5 baths |
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.
| CORAL HAMMOCK | 2 Bedroom Condo | Key West, FL | 2 bedrooms 2.5 baths |
$150 - $1,906 |
CORAL CARIBE: Located in the Coral Hammock gated community, this 2 bedroom 2.5 bath townhome has all the amenities and comforts of home. Community pool is steps away, and lushly landscaped grounds and walking paths create an elegant ambience and the utmost in privacy. Minutes away from beaches and favorite locals restaurants.
| 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 | 3 Bedroom Home | Key West, FL | 3 bedrooms 2 baths |
$450 - $5,655 |
BAHAMA DREAMING: A beautifully renovated Conch house conveniently located in the center of Old Town, one-half block behind Duval Street. 3 bedrooms and 2 baths with queen sleeper sofa offers a comfortable sanctuary for up to 8 people. Private backyard for lounging by the pool and dining outdoors make this home an ideal choice to enjoy both the quiet and chaotic sides of Key West.
| OCEAN SIDE | 2 Bedroom Condo | Key West, FL | 2 bedrooms 2 baths |
$220 - $2,281 |
PAPAYA PLACE: This spacious 2 bedroom 2 bath condominium at 1800 Atlantic offers a wonderful relaxing view of the nature preserve next door and the ocean beyond. Well-equipped with all the modern conveniences. Enjoy the peace and quiet of the tucked away balconies, far from the reaches of the world, allowing you to be lost in the tropical breezes.
| OLD TOWN | 2 Bedroom Home | Key West, FL | 2 bedrooms 2.5 baths |
$340 - $4,350 |
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.
| OLD TOWN | 6 Bedroom Home | Key West, FL | 6 bedrooms 5.5 baths |
$1,195 - $15,950 |
DUVAL COMPOUND: Perfect location! In the heart of historic Old Town Key West just steps from restaurants, bars, theatres and shops, this sprawling 6 bedroom, 5 full bathroom, 2 half bath compound has two private swimming pools, endless porches, terraces and a huge, fabulous roof deck that overlooks the action on Duval Street.