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.

138 properties available

Looking to make a big ‘splash’ for your next tropical vacation? MERMAID MAGIC is your answer! This newly built elevated 2 bedroom home offers incredible views and easy access to the beautiful waters of the Florida Keys. In addition, you’ll have access to the wonderful on-site amenities offered at Venture Out Resort: a heated 80-foot pool with large

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Mermaid Magic

Private Home

$300^.00 - $1,004^.00 / per night

Resembling a French Plantation, PLANTATION TROPICALE is an impressive island estate that occupies an entire corner block of the desirable Casa East neighborhood of Key West. This expansive property features nearly 3,000 square feet of indoor living space, a separate Guest House, beautifully maintained gardens, and a large private pool and cabana –

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Plantation Tropicale

Compound

$1,045^.00 - $5,100^.00 / per night

Imagine a home with floor-to-ceiling panoramic views of the Atlantic Ocean from every room. WINDSWEPT PALMS has been thoughtfully decorated and furnished. The modern, upscale furniture is complemented with splashes of color throughout the home. The balcony wraps 270 degrees around the condo, with seating for everyone in your group. WINDSWEPT PALMS

Windswept Palms

Condo

$445^.00 - $2,426^.00 / per night

If you’d like to spend your month in a neighborhood engulfed in as much history as the Matecumbe Keys, look no further! Located on William Street in Old Town atop the Seaport Inn, MATECUMBE SUITE offers simple island comfort matched with easy access to all the action and historical landmarks. When you add on Last Key Realty’s Five-Star Guest Servic

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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)

Matecumbe Suite

Condo

$205^.00 - $497^.00 / per night

1 bedrooms

1 baths

4 guests

In the same way that the island of Key West has captured the hearts of so many, this charming monthly vacation home will capture yours. ISLAND INSPIRATION combines the appearance and charm of a historic Keys home, with all of the modern conveniences you have come to appreciate. This special home is situated on Margaret Street at the edge of where O

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Island Inspiration

Private Home

$275^.00 - $971^.00 / per night

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

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The Lark's Landing

Condo

$210^.00 - $760^.00 / per night

A trip to Key West is like a breath of fresh air! The sounds of rustling palm trees, the scent of fragrant flowers and the smell of salt air are the rejuvenation that only the tropics can provide. This home is a breath of Key West fresh air, or BRISA FRESCA, a timeless, beach-inspired home that seems to be straight out of the pages of Coastal Livin

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Brisa Fresca

Private Home

$860^.00 - $2,446^.00 / per night

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

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Belle of the Beach

Private Home

$1,100^.00 - $4,382^.00 / per night

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

Baypoint Oasis

Private Home

$281^.00 - $972^.00 / per night

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

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Villa Cubana

Townhome

$300^.00 - $1,394^.00 / per night

When the ‘Welcome to Key West’ sign hits your eye, like a big pizza pie, THAT’S AMORE! If you’ve ever visited Key West, you know how easy it is to fall in love with the charm of this little island. It’s even easier to fall in love when staying in a lavishly decorated and furnished, fully stocked, historic home in the heart of Old Town, and THAT’S A

That's Amore!

Private Home

$333^.00 - $1,125^.00 / per night

Key West is known for having amazing properties, but one home stands tall above the rest with its six majestic Royal Palm trees. HOUSE OF THE ROYAL PALMS features a spacious exterior that will make even the most high-end influencer envious. You’ll be spoiled with multiple seating areas, an oversized covered porch, and a swimming pool, all set under

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New Property

House of the Royal Palms

Private Home

$1,200^.00 - $4,788^.00 / per night

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