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 129 properties available
If you’ve recently heard the Siren’s call beckoning you to Key West, it might be because you were drawn by the SIREN’S SERENADE luxurious interior, lush private backyard, and dream-like location. The moment you enter the gate, you’ll meet the Siren posed in her tropical garden. You’ll come around the lavish and very private pool area to enter this
Siren's Serenade
Private Home
$999.00 - $4,109.00 / per night
Bedrooms 5 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (3)
THE DUKE & THE DUCHESS is a compound fit for a Queen, her King, and their whole court! These newly built, professionally designed side-by-side homes have everything you could desire for a large group vacation - a prime location, coveted amenities, and plenty of space. Your stay at the THE DUKE & THE DUCHESS also includes Last Key Realty's F
The Duke & The Duchess
Compound Pet Friendly
$1,200.00 - $7,210.00 / per night
Bedrooms 7 bedrooms
Bathrooms 8 baths
Guests 22 guests
When exploring Old Town Key West it is typical to stumble upon a surprise tropical bloom that reminds you of the magic of the island you have found yourself on. At the right time of year when enjoying the private garden of this townhouse, you may look up into the trees and spot a bunch of bananas smiling down on you. BANANA BLOSSOMS surprises you w
Banana Blossoms
Townhome
$430.00 - $1,736.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (33)
This precious 2 bedroom cottage with its coral front door will charm you from the moment you walk in the front gate. The front porch is private, for some quiet time reading a book. Inside, you'll see that PUERTA CORALINA reflects the simpler side of tropical living but with some useful updates.THE LIVING AREA...The living room of PUERTA CORALINA is
Puerta Coralina
Private Home Pet Friendly
$370.00 - $2,598.00 / per night
Bedrooms 2 bedrooms
Bathrooms 3 baths
Guests 6 guests
Rating 5 (230)
Walking along Duval Street dreaming of the ideal Key West vacation destination, scanning the rooftops for possibilities, at first you’ll miss this hidden gem completely…but once you discover MAYA’S SECRET TREASURE, you will know you have found the ultimate home base to enjoy Key West. Perched above Duval Street, this beautifully modern condo offers
Maya's Secret Treasure
Condo Pet Friendly
$599.00 - $3,500.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 6 guests
Rating 5 (79)
SOUTHERNMOST VISTAS has everything you’re looking for to spend an unforgettable month in Key West. This recently built multi-story home plus rooftop sun deck exudes a wonderful blend of modern and island vibes. Featuring an open living plan, a lovely heated pool, and a spacious rooftop sundeck with incredible views of the Atlantic Ocean and histori
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)
Southernmost Vistas
Private Home Pet Friendly
$300.00 - $1,150.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 10 guests
A home designed to impress the most discerning travelers, LAYOVER IN PARADISE is an oasis of comfort sure to meet the expectations of those accustomed to first class treatment. LAYOVER IN PARADISE is a newly constructed private home in the Casa Marina neighborhood that offers three spacious private suites, each with a large en-suite bathroom - and
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)
Layover In Paradise
Private Home Pet Friendly
$295.00 - $895.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Formerly known as Playland in Paradise, the ultimate Keys vacation awaits you at BAYPOINT OASIS! This spacious waterfront property is perfect for large groups, featuring an open floor plan, six bedrooms, including three master suites, and expansive outdoor space. BAYPOINT OASIS offers every amenity you could ask for in a vacation home… and then som
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)
Baypoint Oasis
Private Home Pet Friendly
$255.00 - $1,311.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 12 guests
Rating 5 (2)
Dreaming of vacationing in a beautiful home, hitting the links on a tropical island, and cooling off with a dip in one of the Keys’ largest pools? A stay at KESTRAL KOVE will turn this lovely dream into a month-long reality. This 2 bedroom townhome is centrally located on the gated grounds of the Key West Golf Club. KESTRAL KOVE is steps away from
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)
Kestral Kove
Townhome
$155.00 - $547.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 7 guests
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
Guests 20 guests
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 - $5,568.00 / per night
Bedrooms 5 bedrooms
Bathrooms 5 baths
Guests 12 guests
Rating 5 (7)
Escape the “changing tides” of your day-to-day routine by spending a month in the Keys. MARINER’S HIDDEN HAVEN provides an ideal island setting for re-centering your compass by way of your own private waterfront retreat. Picture mornings sipping coffee on the dock, lazy days by the pool, and beautiful sunsets on your boat. The home’s open layout an
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)
Mariner's Hidden Haven
Private Home Pet Friendly
$175.00 - $568.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 5 (1)

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