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
LA PETITE PENTHOUSE is a jewel-like second-story condo in the Shipyard at the Truman Annex, a gated community located in the very heart of Old Town Key West. You'll be just steps from Mallory Square, Duval Street and all the attractions Key West has to offer. Yet, you'll have all of the peace and quiet that comes with a gated community.THE LIVING A
La Petite Penthouse
Condo
$269.00 - $1,031.00 / per night
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 5 (72)
The moment you arrive at CASA AMARILLA and see the dual rocking chairs beckoning you to the front porch, you’ll feel the weight of the world start to lift from your shoulders as your vacation truly begins. Upon entering this adorable cottage, you’ll see the quaint interior is the perfect place to unwind, offering cozy bedrooms, a fully stocked kitc
Hot HOT 32
Casa Amarilla
Private Home Pet Friendly
$468.00 - $3,022.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (59)
GULFSIDE VISTAS is a beautiful penthouse condo and is the perfect place to spend your stay in Key West, with panoramic views of the Gulf and cruise ships as they dock nearby. You'll have ocean views on three sides of GULFSIDE VISTAS, and two spacious balconies as well.Compliance with Truman Annex Community Rules & Regulations is expected of all
Gulfside Vistas
Condo
$430.00 - $1,706.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (91)
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
Seaport Sensation
Townhome Pet Friendly
$275.00 - $941.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
SEA CAPTAIN'S HAVEN is an immaculately furnished villa at the Porter Court Complex in Truman Annex, Key West's most desirable gated community, right in the middle of Old Town. At SEA CAPTAIN'S HAVEN, you'll be close to all of Key West's best restaurants and attractions, including Mallory Square and Fort Zachary Taylor State Park.THE LIVING AREA...S
Sea Captain's Haven
Townhome
$315.00 - $1,319.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (22)
Get the gang together for the ultimate Key West Beach Vacation in a one-of-a-kind giant of an island beach house, BELLE OF THE BEACH. Fully renovated to exceed the highest level of quality and comfort as a large family vacation home, this private estate occupies an entire corner lot, just a block from Smathers Beach. This stilted home allows for a
Belle of the Beach
Private Home Pet Friendly
$850.00 - $4,808.00 / per night
Bedrooms 6 bedrooms
Bathrooms 6 baths
Guests 16 guests
Rating 5 (62)
Like the mystical flower this home is named after, THE ENCHANTED ROSE is a breathtaking monthly vacation home that stands out from the rest. Situated on Rose Street, in the Beachside district of Key West, just a couple blocks from Smathers Beach, this recently renovated one-story home provides a magical setting for vacationers looking to experience
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)
The Enchanted Rose
Private Home Pet Friendly
$225.00 - $844.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 10 guests
Rating 5 (1)
NATURE'S EDGE is a well maintained condo that is located at 1800 Atlantic Blvd on the beach, just steps from the ocean and sand in your toes. You'll enjoy peace and quiet on your balcony, with the Key West Nature Preserve just outside your door. NATURE'S EDGE is located in an upscale private community within walking or biking distance to all of you
Nature's Edge
Condo
$200.00 - $1,378.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (27)
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 - $7,007.00 / per night
Bedrooms 9 bedrooms
Bathrooms 9 baths
Guests 22 guests
Rating 5 (4)
According to the classic song, the best remedy for a belly ache is to "put de lime in de coconut and drink 'em bot' up." Last Key Realty now has the best remedy for finding comfortable accommodations for a large group vacationing in Key West: Reserve THE LIME & THE COCONUT and let us handle de rest! THE LIME & THE COCONUT is a compound of t
The Lime & The Coconut
Compound Pet Friendly
$1,000.00 - $5,862.00 / per night
Bedrooms 6 bedrooms
Bathrooms 6 baths
Guests 16 guests
Rating 5 (28)
This colorful two story Old Town cottage is just right for a delightful stay in the Conch Republic. VILLA CUBANA is located right in Old Town, one block away from Duval Street and smack dab in the center of the fun. You couldn't be any closer to the nightlife and attractions of downtown, yet you are tucked away in a quiet gated community you would
Villa Cubana
Townhome
$300.00 - $1,522.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating 5 (79)
Hunting for the perfect Key West vacation home can feel like a daunting task. However, once you discover TRUMAN’S TROVE, you’ll know that you’ve struck gold! This two-story private home has been beautifully furnished and designed to the highest standard. In addition, TRUMAN’S TROVE offers an ideal location within Truman Annex, Key West’s most exclu
Truman's Trove
Private Home
$444.00 - $1,628.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (1)

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