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 133 properties available
ATLANTIC REFLECTIONS is a newly renovated water view condo that has been meticulously furnished with a modern tropical feel, with spectacular views of the neighboring nature preserve and the ocean beyond, with no end in sight. You'll be able to enjoy those famous Key West sunsets from the living room, and sunrise shadows from your bedroom balconies
Atlantic Reflections
Condo
$330.00 - $1,667.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (227)
Travelers from around the world would agree spending a month in Key West is truly a magical experience, especially when you find two classic conch homes made into one. This cozy compound perfectly captures the magic of the island, with its beautiful Dade County Pine walls, tropical decor, and the plunge pool waiting just outside. MARGARET’S MAGIC
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)
Margaret's Magic Compound
Compound Pet Friendly
$330.00 - $1,194.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Half-Bathroom 1 half-baths
Guests 8 guests
OCTOPUS'S GARDEN has been whimsically decorated with furnishings that reflect the laid-back, quirky island life style of Key West. Located in the gated community of Coral Hammock, you will be just down the street from the famous Hogfish Bar & Grill, Roostica Pizzeria, Hurricane Hole Marina & Restaurant and Chico's Cantina. The Key West Golf
Hot HOT 41
Octopus's Garden
Private Home
$250.00 - $1,248.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (385)
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 71
The Lark's Landing
Condo
$210.00 - $791.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (36)
From the moment you arrive to this spectacular Florida Keys home, you will feel all your stresses and worries simply melt away. CAREFREE ON CUDJOE is an expansive waterfront property that evokes the easy-going nature of Keys living and provides an ideal setting for those looking to enjoy a ‘carefree’ vacation. There will certainly not be a shortage
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)
Carefree on Cudjoe
Private Home Pet Friendly
$265.00 - $1,036.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 9 guests
Rating 5 (3)
As Neptune was known as the Roman God of the Sea, NEPTUNE'S PENTHOUSE is known as the crown jewel of the 1800 Atlantic complex overlooking the Sea. This Penthouse Condominium has a lavish wrap-around balcony that overlooks the Atlantic Ocean and Community Pool below. You'll be able to enjoy the refreshing Key West breezes from atop your own private
Hot HOT 169
Neptune's Penthouse
Condo
$366.00 - $1,844.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (254)
Key West is known for all things lime: Key Lime Pies, Margaritas, and now, THE ZESTY LIME, a rare gem in the heart of Old Town Key West that captures the essence of classic Key West in a completely renovated modern design. THE ZESTY LIME includes all of the coveted amenities of a vacation home: a spacious living area, an ideal bedroom and bathroom
Hot HOT 45
The Zesty Lime
Private Home Pet Friendly
$500.00 - $2,762.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Half-Bathroom 1 half-baths
Guests 8 guests
Rating 5 (156)
Finding a compound like THE THREE MERMAIDS in Key West is as rare as finding actual mermaids! From the pristine, modern decor, to the fun, nostalgic appliances and the ample amount of space in an ideal Old Town location, this compound is truly a one-of-a-kind. Featuring 3 stunning, freshly-built homes on one lot, with a beautiful swimming pool betw
Hot HOT 44
New Property New Property
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)
The Three Mermaids
Compound Pet Friendly
$500.00 - $1,398.00 / per night
Bedrooms 5 bedrooms
Bathrooms 4 baths
Half-Bathroom 1 half-baths
Guests 12 guests
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 28
Diamond Girl
Private Home
$850.00 - $3,751.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (24)
SET SAIL celebrates the experiences of the Keys, both on the water and on land. The ideal complementary home base for your water-based excursions awaits in this condo just steps from the marina. SET SAIL is a well-appointed first floor condo located in the waterfront community of Coconut Mallory Resort & Marina, which offers two large community
Hot HOT 180
Set Sail
Condo
$200.00 - $905.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (138)
Throughout Key West you'll find subtle touches of coconuts; from the towering coconut palms nestled throughout the streets of Old Town to folks sipping from fresh coconuts while soaking up the sun, and now, you can add THE TOASTED COCONUT to that list. THE TOASTED COCONUT is a rare gem in the heart of Old Town Key West that captures the essence of
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The Toasted Coconut
Private Home Pet Friendly
$500.00 - $2,621.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Half-Bathroom 1 half-baths
Guests 8 guests
Rating 5 (142)
CASA VICTORIA, located in the heart of Old Town just two blocks from Duval Street, is a large 5 bedroom home built with the charm and quirkiness of early 20th century Key West. Dating back to the Cigar Manufacturers' era, CASA VICTORIA exudes the classic Old Town style that makes Key West such a unique vacation experience. This authentic Conch Hous
Hot HOT 53
Casa Victoria
Private Home Pet Friendly
$995.00 - $5,407.00 / per night
Bedrooms 5 bedrooms
Bathrooms 5 baths
Half-Bathroom 1 half-baths
Guests 12 guests
Rating 5 (366)

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