Old Town ~ Key West Vacation Rentals

SPA ON DUVAL: A tropical 2-story, 2 bedroom 2.5bath townhome located in the rooftop community of Duval Square where you only have to walk downstairs to great restaurants, specialty shops and the action of Duval Street. Catch the rays on the pool deck or soothe tired muscles in the private jacuzzi on your own deck. Spa On Duval is truly a Key West experience to enjoy.

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.

SOUTHARD RETREAT (monthly rental): This is a choice location with lush tropical garden and beautiful swimming pool offering a peaceful setting behind the privacy wall, yet just a few blocks from the eclectic activity of Old Town Key West. 2 bedrooms 2 baths located in the Southard Square condominium complex with off-street parking.

DUVAL COURTYARD: Located just steps from famous Duval Street in the rooftop community of Duval Square, this 3 bedroom 2 bath condo has plenty of space, a fabulous location and all the amenities you could wish for. Take in the sights of Old Town, relax on your private balcony to rejuvenate; then do it all again!

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...

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.

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.

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!

ISLAND PEARL: True island living in this 1 loft bedroom 1 bath cottage located in the heart of Old Town Key West. French doors that open to a creative deck surrounded by tropical foliage with private jacuzzi and pool for you alone. Half a block from Duval Street and across the street from our infamous local grocery, Fausto's Food Palace. Heaven...

ISLAND WIND: Welcome to a tropical sun-drenched oasis in the heart of Old Town. This charming 2 bedroom 2 bath Bahamian-style townhome, with tin roof and white spindled decks reminiscent of Old Key West, is located in award-winning Windward Park, a gated and secure compound. Soothe your weary muscles in your private jacuzzi after taking in the sights all day.

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.

THE VICTORIA HOUSE: This gracious historic property, dating from the early 20th century, was built by prominent cigar manufacturer, William Otis Johnson. 5 bedrooms 5.5 baths with pool and jacuzzi offers your friends and family the finest of acccommodations. Conveniently located on Truman Avenue, 2 blocks from Duval Street. This home has it all!

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.

ARTIST HOUSE: Located within the gated rooftop community of Duval Square, this 2 bedroom 2.5 bath with sleeper sofa and beautifully decorated, is perfectly located so that you can park your car in the private lot and walk downstairs to restaurants, specialty stores, attractions and nightlife of Old Town Key West. When you have had your fill, soak in the jacuzzi on your private deck.

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.

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.

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.

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!

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.

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.

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...

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.

EGRET COTTAGE: Enjoy your own sweet 1 bedroom cottage with private deck in a charming compound nestled in the heart of historic Old Town Key West, two blocks from Duval Street with its incredible art galleries, boutiques, museums, attractions, restaurants, and nightclubs. Close enough when you want it, far enough when you don't.

ANNE'S HIDEAWAY (monthly rental): Relax and unwind in this historic 2 bedroom 2 bath Conch home with original Key West architecture and private pool. Tucked away in a quiet area of Old Town, this home has it all, privacy at home with all the modern conveniences, yet a short walk or bike ride to the downtown Duval Street activities, entertainment, restaurants and shopping.

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.