Located on Florida’s southern coast, Florida Keys is a popular holiday destination with beautiful beaches, incredible wildlife and delicious seafood. There are many things to see, do, and discover in Florida Keys. Top on the list is visiting John Pennekamp Coral Reef State Park in Key Largo, the first undersea park in the USA with a thriving coral reef and plenty of undersea activities. Fall in love with nature at Key West Butterfly and Nature Conservatory, a habitat for different species of live butterflies and birds. After a long day of exploring the sights, go back to your cozy nook on the island and unwind in a private pool. Want to know more? Scroll down for the best vacation rentals with private pool in Florida Keys, Florida.
We handpicked these listings carefully, considering (wherever possible) host status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and access to private pool. The image galleries get refreshed with the latest updates regularly. They were last updated on October 29, 2025.
1. Beachfront residence close to conveniences, Key Largo
Have an enjoyable vacation at this charming beachfront residence with a private pool in Key Largo. Enjoy swimming in the waters of the heated pool during the day or night. The property boasts stunning sea views, beautifully decorated interiors and a well-equipped kitchen to whip up meals. Admire the sunset views from the outdoor deck equipped with plush patio furniture as you sip your favourite cocktail.
The rental is close to popular eateries and shops for a great time exploring the best of Key Largo.
Key Largo, Florida, United States
Top guest reviews
Location:
great location that feels very privateoverall a great trip at a great house in an exceptional location on the watergreat house in an amazing location that was even better than advertisedRead more reviewsAmenities & Room:
the beds were incredibly comfortable the outside with the pool dock beach paddle boards etc
2. Coco Plum Paradise, Marathon
Nothing beats the spectacular ocean view at this tropical bayfront home in Marathon. The property has a private dock and enjoys direct ocean access for guests who love boating, fishing, kayaking and endless fun under the sun. After a long day out, retreat to your private in-ground pool for relaxing moments surrounded by shady palms. You can even enjoy a heated pool for an additional weekly fee.
Aside from comfortably furnished bedrooms, the rental has a fully equipped kitchen, a tastefully decorated living room with plush sofas and a spacious patio to capture the lovely sunrise. There is a recreation room in the basement equipped with a table tennis and a TV to entertain the kids.
Marathon, Florida, United States
Top guest reviews
Host:
the owners were great at communicating with usthe host are wonderful and very easy to communicate withCleanliness:
very clean open and bright… although we didn’t spend very much time insideproperty is clean and has everything you could possibly needproperty was very well maintained very clean and owners were very accommodatingRead more reviewsAmenities & Room:
the pool hot tub porch dock and downstairs entertainment was the highlight of this house
3. Palm Villa - Villa 5115, Marathon
Take advantage of the private pool to enjoy cool soaks next to nature at this lovely villa in Duck Key, Marathon. The beautifully designed property has a pretty entrance with a white picket fence, minimalist interiors that maximise space and a balcony overlooking streetscapes. Head to the covered poolside patio equipped with deck chairs and a cushioned love seat to snuggle up with your partner.
The host provides a kayak, paddleboard and life jackets for guests to go fishing or boating at the nearby Duck Key Marina or Little Conch Key. For more adventures, the rental has two bicycles with helmets for cycling fun around the vicinity.
Duck Key, Florida, United States
Top guest reviews
Host:
rating details: the property manager was very helpfulrating details: the property manager was very helpfulrating details: the property manager was very helpfulrating details: the property manager was very helpfulrating details: the property manager was very helpfulLocation:
the location of this property is greatthe location and general layout of this property is perfect for our getawaycentrally located peaceful place to stay while vacationing in the keyscentrally located peaceful place to stay while vacationing in the keysthe house was great and in a awesome locationCleanliness:
villa was clean and comfortablevilla was clean and comfortablethe property was beautiful very clean and comfortablethe neighborhood was very clean and quietthe condo was super clean and the bed was comfortableRead more reviewsAmenities & Room:
the pool and back deck very relaxingenjoyed the pool and all the amenitiesenjoyed the pool and all the amenitiesthe pool is a great addition and very relaxing with the chairs and fanthe pool is a great addition and very relaxing with the chairs and fan
4. Oceanfront haven with private heated pool, Cudjoe Key (from USD 458)
Experience sweeping views of the Atlantic Ocean from this contemporary home with a private heated pool in Cudjoe Key. The property boasts a lovely in-ground pool for relaxing swims and poolside deck chairs for perfecting your tan under shady palms. Stellar amenities include a well-equipped kitchen and a covered patio with a comfortable dining area to enjoy your meal. Previous guests were impressed by the cleanliness of the premises and its excellent location for beach adventures.
Cudjoe Key, Florida, United States
Top guest reviews
Host:
host was very responsivethe host was extremely nice and was available to helpwe absolutely enjoyed our recent stay at this great property mitch was a wonderful hostmitch was attentive and helpful with suggestions and checking in on our staymitch was very helpfulLocation:
we loved the location and the housethe price is great for the location and all the things it providesgreat place to stay for family and friendsgreat place for large groups with adult kidsRead more reviewsCleanliness:
the property was clean and well maintainedthe property was clean and well laid out as advertisedmade sure property was clean every day
5. Mockingbird Pointe, Marathon
Chill out and relax at this gorgeous waterfront home with stunning views of Sombrero Lagoon in Marathon. Enjoy swimming in warm water as the property has a heated in-ground swimming pool with a splash deck. This vacation rental is perfect for fishing enthusiasts as it has a protected dock with a bait freezer, underwater fish lighting, a lighted fish-cleaning station and an outdoor shower.
Outstanding amenities include a fully equipped kitchen, entertainment options and ample parking for vehicles. The host provides kayaks, canoes, life jackets, water sports gear and bicycles with helmets to ensure you enjoy an exciting time outdoors.
Marathon, Florida, United States
Top guest reviews
Host:
hosts were so kind to call the day after check in and ask if we had any questionsphil and linda were wonderful hosts and the house was absolutely gorgeousLocation:
good central location and a very nice neighborhoodawesome waterfront property with great location close to 7 mile bridgethis was an ideal place for our family of fourCleanliness:
it was well stocked clean and comfortablethe house was very clean and had everything we neededRead more reviewsAmenities & Room:
really enjoyed the heated pool and the sometimes often-overlooked items such as a bait freezer kayaks and bikesbeds were very comfy and the bathrooms were so nicewell-equipped with everything one could need and we loved the tiki hut and pool
6. Island home with spacious wraparound porch, Tavernier (from USD 500)
Spacious, well furnished and inviting is this island home in Tavernier. The property has a beautiful private pool with poolside sun loungers. You can make use of the kayaks and paddles along with the life jackets, while your kids splash around using the floatation gears available. Another advantage is the impressive wraparound porch to watch the stunning sunrise and sunset over the saltwater basin. After a tiring day, retreat to plush comfort in well-appointed bedrooms or lounge in the living room with a comfortable settee and entertainment options.
Do you love photographing nature? Keep a lookout for manatees and dolphins swimming in the bay.
Tavernier , FL, US
7. Bahama House, Key West (from USD 930)
Soak up plenty of sunshine by the lovely private pool at this modern vacation home in Key West. The tastefully furnished property has a fully equipped kitchen, private parking, laundry facilities and a separate studio cottage for guests who need privacy. Step outside to the spacious covered deck equipped with comfortable patio furniture or snooze on the poolside sun loungers surrounded by flourishing greens.
Located off Duval Street, the rental is a short stroll to stores, eateries and museums, such as the Ernest Hemingway Home & Museum. Dogs are welcome on the premises with an additional nightly fee.
Key West, Florida, United States
Top guest reviews
Host:
beautiful home and friendly stayLocation:
the location of the house is perfectgreat location to good restaurants shopping and entertainmentgreat location just off duval but quietgreat location and perfect little houseshort walk to beach or great restaurants and not too far to walk to the tourist spotsCleanliness:
clean and spacious for 6 adultsoverall quite cleancomfortable and clean accommodationsclean and great locationRead more reviewsAmenities & Room:
nice little house with a cozy backyard pool
8. Casa Amor, Key West
Discover the perfect getaway at this spacious tropical retreat with a gorgeous private pool in Key West. Enjoy a dip in the pool surrounded by flourishing palms before retreating indoors to the well-furnished living room with plush sofas for relaxation.
The historic property was previously a bottling plant and today is a modern vacation rental with stylish interiors and convenient amenities. Outstanding features include a fully equipped kitchen, laundry facilities, free parking and an outdoor deck with poolside patio furniture to enjoy the sunshine.
Accommodates: 10
Minimum Nights: 2
Refund Policy : 100% refund if you cancel at least 30 days before check-in.
Top guest reviews
Host:
propert manager was very responsive to questionsrating details: the property manager was very helpfulrating details: the property manager was very helpfulrating details: the property manager was very helpfulrating details: the property manager was very helpfulLocation:
ideally located within walking or biking distance to just about everythingthe location was perfect for our familyit’s location is great being within walking distance to everything whether it be the beach or duval streetplenty of room and a great locationi highly recommend this locationCleanliness:
thanks again to shana
the house was impeccably cleanRead more reviewsAmenities & Room:
the pool deck was nice and privatepool area can get slippery so a bath mat for the doorway would be saferthe house was spacious and accommodating with a beautiful lanai and pool area
9. Key Lime Kottage, Grassy Key
Are you looking for a private and secluded place to holiday? This beautiful cottage in Grassy Key with no neighbours nearby is your dream escape. It’s perfect for nature lovers as the property has lush mangroves with several varieties of native birds roaming the grounds.
Additionally, the rental boasts a gorgeous heated pool with poolside sun loungers and a private hot tub in the pool enclosure for your enjoyment. Stellar features include a dining table that seats up to eight guests, a fully equipped kitchen, laundry facilities, a smart TV and books to keep you entertained at home. Previous guests praised the well-maintained home and communicative hosts who attended to queries promptly.
Accommodates: 6
Minimum Nights: 7
Refund Policy : 100% refund if you cancel at least 30 days before check-in.
Top guest reviews
Host:
even with the owner change it is still a private paradisewonderful place and very peaceful everything was great and property owners were easily accessible if neededthanks for hosting such an awesome vacation propertyLocation:
great place to relax and enjoy the wildlife awesome location to visit many cool beachesgreat location clean and neat best vacation everpool and spa were amazing loved the central location and also the privacy the property providedCleanliness:
clean well kept and appropriately stockedwell maintained and cleanproperty is well kept and cleankey lime kottage was exactly what we wanted for vacation nice clean waterfront property with a heated poolRead more reviewsAmenities & Room:
the pool/spa area was a fantastic space
10. Impressive home with private courtyard, Key West
Happiness for water lovers means spending the day by the beautiful private pool at this impressive home in Key West. You’ll love the flowers blooming on the outdoor deck in the private courtyard and poolside patio furniture to enjoy some sunshine. Convenient amenities include a well-equipped kitchen, laundry facilities, a flat-screen TV and a private hot tub to relax with your best buddy.
Are you a beach lover? The property is close to a lovely beach at Fort Taylor State Park for exciting seaside adventures. It’s also within walking distance to local restaurants, shops and entertainment outlets in town for a grand day out.
Key West, Florida, United States
Top guest reviews
Host:
owner is very responsivedavid the owner very nice and responded to all questionsthe owner was very accommodating to our needs and the home was beautifulthe owner was easy to contact and was very helpfulthe owner seemed very nice in personLocation:
location was the best partthe location of the property was perfectthe location made for an easy walk to the hemingway house butterfly conservatory and many nice restaurantsbeautiful property and nice and quiet in central part of the actiongreat place to stayCleanliness:
the house was clean and well maintained otherwisethe house is exactly as pictured & very cleanwe loved the layout of this property the house was clean comfortable and the pool area was very privateRead more reviewsAmenities & Room:
we especially enjoyed the quiet of the courtyard pool areacool deck area to sit around pool with music decking gets super hotwe really enjoyed the privacy of the patio and poolthe kitchen facilities were adequate for all our cooking and the grill outside worked awesomevery quiet neighborhood and bed was comfortable
Have a fun-filled vacation in Florida Keys
From gorgeous beach resorts to exciting outdoor adventures, a holiday in Florida Keys is hard to beat. Are you planning to avoid crowded communal swimming pools while holidaying? Then, select a great place to stay from this list of the best vacation rentals with private pool in Florida Keys, Florida.
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