Private Pool Homes ~ Florida Keys Rentals

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...

EASY LIVIN': The name says it all! This lovely private 3 bedroom home with pool is located in a secluded cul-de-sac in Truman Annex, a gated community located in historic Old Town Key West. Lounge by the pool in peace and tranquility or take a short walk to Duval Street where you will find the restaurants, bars, and shopping you have heard so much about.

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!

DIAMONDS ON THE WATER: Looking for the ultimate Keys experience? Look no further! Diamonds on the Water will show you the reason people come to the Keys on vacation and never go back. Located on 2 lots, there is plenty of room for entertaining in the house or around the pool plus boat dock space on the canal leading to Florida Bay.

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.

ADMIRAL'S PARADISE:  Style is supreme in this 3 bedroom 3.5 bath single family home on Admiral's Lane in the exclusive Truman Annex community. Enjoy the abundant french doors that open the entire downstairs to the outdoor pool and sun deck, offering an easy open air living experience equal to none. Walk to all there is to see in 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.

BLOOM'N PARADISE: Relax in luxury in this beautiful Truman Annex private home with pool and sun deck. 3 bedrooms and 3 bathrooms in the main house plus a pool house with 1 bedroom 1 bath offers room for friends and family to enjoy peace and solitude while at home, with the chaotic nightlife of downtown Key West just 2 blocks away.

PERFECT PINEAPPLE (monthly rental): Long considered a sign of hospitality, the pineapple is now widely recognized as a sign of Welcome and Friendship...and so we welcome you to the Perfect Pineapple. This quaint Conch cottage, 2 bedrooms 1 bath has all the amenities for your visit, including a side yard where you can sunbathe, swim and BBQ to your heart's content.

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.

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.  

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.

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.

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!

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.

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.

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.

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.

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.

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.

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!

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.