Key West Rentals with Pool

Experience the pinnacle of an island paradise with our luxurious Key West rentals, each featuring a private pool. Enjoy your private retreat's ultimate blend of sun, fun, and turquoise water. Our offerings span a diverse range, from cozy two-bedroom homes to grand eight-bedroom estates, all meticulously designed to cater to your unique preferences.

Embrace the warm Key West sun as you dip into your private pool, the perfect respite after exploring the island's many charms. And when the weather cools, our heated pools ensure your swim remains as enjoyable as ever.

Our private pool rentals are excellent for those who value intimacy and privacy. These homes are ideally suited for families and groups, offering the ideal setting for a tranquil vacation. For guests staying a month or longer, pool heating is included in your package, while those on shorter stays can add this feature for a nominal fee during checkout.

But the luxury continues after the pool. Our rental properties have many amenities to ensure complete comfort during your stay. Benefit from our personalized concierge services and a unique on-site property introduction - no need for office check-ins here. Start your vacation the moment you step onto the property.

Spread across the enchanting island of Key West, each of our locations offers its unique charm. Experience a truly luxurious getaway in our private pool rentals and uncover the true essence of a Key West vacation.


Properties Available 138 properties available
In Key West, every day is a celebration of what makes Summer such a beloved season - warm weather, no agendas, and spending quality time with family and friends. "Summer Solstice" provides the perfect setting for a large group looking to enjoy exactly that. As a combination of two side-by-side private homes located in the heart of Old Town, "Summer
Summer Solstice
Compound Pet Friendly
$1,350.00 - $6,434.00 / per night
Bedrooms 9 bedrooms
Bathrooms 9 baths
Half-Bathroom 1 half-baths
Guests 22 guests
Rating 5 (8)
The moment you arrive at this midtown mansion, you’ll know your time in Key West is going to be special. The circular driveway and covered portico provide a grand entrance, which set the stage for what awaits you inside. At over 3,900 square feet, ISLAND OPULENCE is one of the largest private residences in Key West. This impressive ranch-style home
Monthly Rental Monthly Rental
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A week isn't enough time in Key West! This property is available for longer stays of 29 nights+. Please adhere to calendar months if you can. (Due to strict city ordinances we can't offer it for any less time)
Island Opulence
Private Home Pet Friendly
$250.00 - $732.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Half-Bathroom 1 half-baths
Guests 11 guests
Rating 5 (3)
Looking to land at the perfect vacation rental to explore Key West and the Lower Keys? Then look no further than THE LARK’S LANDING. Found on the top floor of Sunrise Suites, THE LARK’S LANDING features all new furniture and TVs, a private balcony, Two Bedroom Suites, a comfortable living room, and a full kitchen. With a location near the entrance
Hot HOT 28
The Lark's Landing
Condo
$210.00 - $796.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (42)
OASIS ON OLIVIA is the perfect setting for a large group looking to experience a month in Key West in style. As a combination of two side-by-side private homes located in the heart of Old Town, OASIS ON OLIVIA offers a prime location and plenty of comfortable accommodations for everyone, as well as numerous luxuries, including two private heated po
Oasis on Olivia
Compound Pet Friendly
Bedrooms 9 bedrooms
Bathrooms 9 baths
Half-Bathroom 1 half-baths
Guests 20 guests
When you think of Key West, you think of spending relaxing days with your toes in the sand under the palm trees, and fun-filled nights walking through the Streets of Old Town on your way to catch the sunset at Mallory Square. Experience these kinds of days (and nights) at SOUTHERNMOST PALMS, a beautifully renovated townhome, located at The Foundry
Hot HOT 37
Southernmost Palms
Townhome
$399.00 - $1,027.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Half-Bathroom 1 half-baths
Guests 6 guests
Rating 5 (102)
SOUTHERNMOST HOSPITALITY V is a luxurious private estate that occupies an entire corner of Old Town's famous Duval Street, just a block from the Southernmost Point. Don't let the address fool you... this upscale home has plenty of privacy in the spacious back yard with a tall fence surrounding the large private pool. Privacy also comes in the form
Southernmost Hospitality V
Private Home Pet Friendly
$800.00 - $5,123.00 / per night
Bedrooms 5 bedrooms
Bathrooms 5 baths
Half-Bathroom 1 half-baths
Guests 12 guests
Rating 5 (73)
All year long you dream of a getaway to capture that feeling of Key West's ENDLESS SUMMER - carefree days spent tooling around Old Town on bicycles or wandering the island streets in flip flops with the sun warming your shoulders. No plans, nowhere to be, no deadlines - only a to-do list of making memories with your family and friends and possibly
Endless Summer
Private Home Pet Friendly
$675.00 - $4,044.00 / per night
Bedrooms 5 bedrooms
Bathrooms 5 baths
Guests 12 guests
Rating 5 (221)
Seals & Crofts said it best: ‘Diamond Girl, you sure do shine.’ Formerly known as Seventh Heaven, DIAMOND GIRL is a stunning two-story private home that epitomizes island living, with its’ distinct exterior eyebrow design, ample indoor and outdoor living space, and comfortable accommodations. Once here you’ll quickly realize this peaceful oasis
Hot HOT 29
Diamond Girl
Private Home
$850.00 - $3,287.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (24)
OLD TOWN OASIS is back! After three years out of the rental program, this luxurious condo has returned, with all the same elegance enjoyed by many guests since 2004, and with many improvements.You’ll be staying right near the ocean in Old Town but with all the quiet and solitude of an exclusive gated community. The Green Parrot (oldest blues bar in
Old Town Oasis
Condo
$325.00 - $1,161.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (46)
It is not so often that something new is built in Old Town, the historic district of Key West known for quintessential conch homes and walkable streets. But recently a spectacular development called Old Town Villas was constructed smack dab in the middle of Old Town. SEAPORT SENSATION is one of the newly built breathtaking townhomes at Old Town Vil
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Monthly Rental
A week isn't enough time in Key West! This property is available for longer stays of 29 nights+. Please adhere to calendar months if you can. (Due to strict city ordinances we can't offer it for any less time)
Seaport Sensation
Townhome Pet Friendly
$275.00 - $867.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Half-Bathroom 1 half-baths
Guests 8 guests
Traveling with a large group requires a special home. To maximize comfort, large common areas are offered both indoor and outdoor. Private bedroom accommodations with en-suite bathrooms and TVs are a must. And don't forget about the location! This home is easily accessible to the favorites of Old Town for when the group (finally) reaches a decision
Monthly Rental Monthly Rental
Monthly Rental
A week isn't enough time in Key West! This property is available for longer stays of 29 nights+. Please adhere to calendar months if you can. (Due to strict city ordinances we can't offer it for any less time)
La Grande Reunion
Private Home Pet Friendly
$395.00 - $1,315.00 / per night
Bedrooms 5 bedrooms
Bathrooms 5 baths
Half-Bathroom 1 half-baths
Guests 10 guests
Rating 5 (28)
OCEANFRONT OASIS is a boater’s paradise featuring incredible views, modern decor, and dockage that can handle a mini yacht. This five-bedroom home provides the ultimate escape for those needing a break from their fast-paced everyday life. Imagine yourself relaxing in the pool, soaking up some sun as you gaze across the endless ocean. When it’s tim
Hot HOT 27
New Property New Property
New Property
Fabulously Fresh New Property!!
Monthly Rental Monthly Rental
Monthly Rental
A week isn't enough time in Key West! This property is available for longer stays of 29 nights+. Please adhere to calendar months if you can. (Due to strict city ordinances we can't offer it for any less time)
Oceanfront Oasis
Private Home Pet Friendly
$400.00 - $1,224.00 / per night
Bedrooms 5 bedrooms
Bathrooms 4 baths
Guests 12 guests

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