Old Town ~ Key West Vacation Rentals

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.

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.

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.

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.

LEEWARD ISLE KEY WEST RETREAT: Dwell in the possibility! 2 bedrooms 2 baths in this newly renovated residence. From the moment you park in the private parking lot, you know you are someplace special. A small gated compound with only 13 homes, you will revel in the peace and quiet, while still being located right in the heart of Old Town.

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!

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...

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!

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.

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.

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.

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!

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.

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 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.

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.

EXHALE (monthly rental): Located on a quiet tree lined street in the heart of Old Town, you will enter into a a tropical escape surrounded by sunshine, ocean breezes and EXHALE. A quaint cottage with the true spirit of Key West combining indoor and outdoor living into one. Walking or biking distance to anything you will want to do while enjoying the lifestyle of a local.

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.

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!

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 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...

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.

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.

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.

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.