Top 8 Vacation Rentals With Private Pool In Clearwater, Florida - Updated 2024

Leizle Anne
Leizle Anne  
| 4 min read

With its crystal-clear beaches, such as the renowned eponymous beach, this city of Clearwater promises endless seaside charm. For fans of marine life, Clearwater Marine Aquarium, home to Winter, the adorable dolphin, is a must-visit. Outdoor enthusiasts will appreciate the many parks, such as Moccasin Lake Nature Park and Wright Park, where local wildlife and lush greenery take center stage. And if you’re a fan of baseball, you’ll enjoy the thrill of a game at BayCare Ballpark, the spring training ground for the Philadelphia Phillies. When the day’s adventures come to an end, you’ll need a tranquil and comfortable place to retreat where you can soak in a private pool under the warm Florida sky. Check out our list of the top vacation rentals with private pool in Clearwater, Florida, for a rejuvenating stay.

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 April 14, 2024.

1. Charming 1950s vacation home (from USD 194)

Step into the timeless charm of the 1950s with this Clearwater vacation home. After a day of exploration, dive into the private pool or unwind in the hot tub. The pool may not be heated, but it offers a refreshing plunge under Florida’s radiant sun.

The home’s custom kitchen comes fully equipped, making it ideal for whipping up delicious meals. And with a tankless water heater, your comfort is guaranteed. Enjoy your homemade meals on the balcony as you look over the lush fenced yard adorned with various plants.

Stayed at this property?
Clearwater, Florida, United States
1.24 km (0.8 mi) from Crest Lake Park
PRIVATE VACATION HOME 8 Guests 3 Bedrooms 1 Bathroom

Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.

2. Sunlit home near Clearwater Beach (from USD 192)

Embrace the vibrant beach vibes of this private Clearwater oasis. Near the award-winning Clearwater Beach, this vibrant home is your ideal getaway spot. Bask in the sun with a dip in the inviting private pool or a stretch on the poolside loungers. The backyard area also features an additional bathroom, which you can use after a visit to the beach.

While here, dine al fresco, take a refreshing swim, or enjoy a lazy afternoon watching TV. Furthermore, the kitchen gleams with new appliances, fostering your culinary creativity. Bright and cheery decorations throughout the house will get you in the mood for your tropical holiday.

Stayed at this property?
Clearwater, Florida, United States
711 meters (0.5 ft) from Crest Lake Park
PRIVATE VACATION HOME 7 Guests 2 Bedrooms 2 Bathrooms

Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.

3. Tranquil poolside retreat (from USD 212)

Indulge in the luxury of a private heated pool in this splendid vacation home. It promises year-round swimming with your loved ones. The pool area, complete with loungers and an outdoor shower, set the stage for an unforgettable stay.

The indoor spaces, boasting cozy bedrooms and state-of-the-art amenities, open directly to the pool, encouraging a free flow between indoor comfort and outdoor relaxation. For maximum enjoyment, you can lounge on the screened patio, fire up the barbecue grill, or simply take in the sunshine on the pool deck.

Stayed at this property?
Clearwater, Florida, United States
2.31 km (1.5 mi) from Crest Lake Park
93 reviews   Superhost Wifi Available
ENTIRE HOME 4 Beds 8 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 8

Top guest reviews
Amenities & Room:
lots of good amenities including a pool and sunroom
this house is decorated beautifully from the couch to the linens to the outdoor space and pool
backyard has several pool chairs to lay out on and enjoy the florida sun
coffee by the pool made every morning perfect pool temperature was lovely
private pool all the comforts and conveniences of home
everything was amazing the house the cleanliness communication the appliances and accommodations
the house was clean and very welcoming
this house is spotlessly clean
perfect for a weekend getaway extremely clean and tidy
very nice property clean and quiet with a beautiful pool
thank you bnb pro host shelly evans
chris was a great host - very responsive and communicative
host was very responsive to all messages
wow what a nice place it was great the host was great
best host answered very fast and also accommodated with us
location was good for short drive to beach areas
we found the location to be an excellent one for stores food and bike/running trails
spacious place and a good location
the neighborhood was super quiet and there were lots of stores and restaurants nearby
we had a wonderful time the location great we had almost everything we needed the whole stay
Read more reviews

4. Newly furnished vacation home with spacious layout (from USD 117)

Experience the grandeur of this newly furnished vacation home. The property showcases an inviting open layout, leading to an exquisite private pool - the star attraction here. While here, you can delight in the game room, recline under the poolside cabana, or retreat to a secluded corner for serene moments. Furthermore, a lap or two in this sparkling pool is perfect to beat the heat.

The home’s location makes for a convenient base to explore Clearwater, only a few minutes from the acclaimed beach and a short stroll to BayCare Ballpark. With numerous shopping and dining options nearby, entertainment is never far off.

Stayed at this property?
Clearwater, Florida, United States
3.36 km (2.1 mi) from Crest Lake Park
66 reviews   Superhost Wifi Available
ENTIRE HOME 4 Beds 8 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 8

Top guest reviews
Amenities & Room:
comfortable furniture and bedding awesome quiet backyard and pool
the pool was awesome with amazing sunset views at night
having the pool was a huge plus too as well as patio furniture & grill
the beds were very comfortable
the pool is a nice size and very relaxing
everything was super good and clean
the property was decorated beautifully with clean and modern touches
liked that the house was clean and uncluttered
it is very well-equipped clean spacious and tastefully decorated
the place is very spacious spotless with beautiful decor
mark was a great host
thank you for being an amazing host for our alaska to florida vacation
mark is a great host and will respond almost immediately if you have any queries
he was very responsive and very accommodating
stay was great house was nice the host communication was quick and mannerly
location perfect for our needs
the location was perfect for our family
mark was in close contact and very helpful
nice area of town that’s very close to many attractions
beautiful home in a quiet neighborhood but still close to shopping restaurants and entertainment
Read more reviews

5. Renovated vacation home across golf course (from USD 190)

This vacation house is your perfect place for an unforgettable getaway. Dive into the sizeable heated pool, open all year round, with ample space to swim and even pool toys to ramp up the fun. You can use the pool any time of the day, so get ready to enjoy a midnight soak under the star-lit night sky.

Positioned close to Clearwater Beach, charming Downtown Dunedin, and Clearwater Country Club, this house has a great location for sightseeing. And to exercise, take the provided bikes to the nearby Fred Marquis Pinellas Trail and explore the trail. Furthermore, shopping, dining, and Seminole Boat Ramp for thrilling water activities are all at your fingertips here.

Stayed at this property?
Clearwater, Florida, United States
1.55 km (1.0 mi) from Crest Lake Park
46 reviews   Superhost Wifi Available
ENTIRE HOME 5 Beds 8 Guests 4 Bedrooms 2 Bathrooms

Accommodates: 8

Top guest reviews
Amenities & Room:
beautiful pool yard and all rooms were perfect
the house was clean and comfortable
the home was nice and superbly clean and well-stocked
great hosts the most clean airbnb we have ever stayed in and had everything we needed
the hosts are auper accommodating and responsive
felt like a brand new home very welcoming thanks for hosting
the location was nice in how close it was to dunedin and clearwater beach
great location and the home had everything we needed and more
Read more reviews

6. Waterfront vacation rental with saltwater pool (from USD 495)

Discover the magic of waterfront living at this beach house. This stunning remodeled home invites families and friends to revel in the joy of a private saltwater pool experience available throughout the year. This pool is located across the water, providing mesmerizing views as you take refreshing dips and soak up the sun. You can also unwind by dolphin-watching at the dockside.

From tranquil seclusion to vibrant social life, find everything within a stroll away. You can also immerse yourself in the outdoor delights, welcoming bars, delightful restaurants, and an active nightlife scene with a stay here.

Stayed at this property?
Clearwater, Florida, United States
4.52 km (2.9 mi) from Crest Lake Park
22 reviews   Wifi Available
ENTIRE HOME 5 Beds 8 Guests 4 Bedrooms 3 Bathrooms

Accommodates: 8

Top guest reviews
Amenities & Room:
the pool was beautiful with a lovely view of the canal
beautiful home seems newly renovated great for families easy to use kitchen quite neighborhood
the beds were awesome
lots of space to lounge and comfortable
yosvani was extremely attentive and wanted to make sure our stay was perfect
great location easy to drive and walk (1mile) to beach and restaurants and groceries
great location quiet neighborhood very nicely updated would stay here again
the neighborhood was a nice area to take early morning walks
Read more reviews

7. Charming homes with exclusive jet ski access

Experience twice the fun and privacy with two separate homes, nestled in a single property in the heart of Clearwater. Boasting its salt-chlorinated pool, these freshly remodeled spaces offer the perfect retreat for groups or large families. Each residence features a separate kitchen and 4K HDR TVs in each room for uninterrupted fun. You can also take advantage of the exclusive discount on jet ski rentals and explore the hidden beach gems accessible only by a boat or jet ski.

Stayed at this property?
Clearwater, Florida, United States
381 meters (0.3 ft) from Crest Lake Park
56 reviews   Wifi Available
ENTIRE HOME 7 Beds 14 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 14

Top guest reviews
Amenities & Room:
we enjoyed the pool and pool deck after we returned from a day on the water
clean well organized and loved how it’s separated in 2 homes with a wooded deck pool and grill
really loved the airbnb so clean and beautifully remodeled
great clean quiet cozy place highly recommend
the house was recently renovated and clean
great space very clean and conveniently located
great location and very clean :)
host was very easy to communicate with
fabio was an awesome host
great place and a very good host thank you
we highly recommend this property and host
host responds fast and will help with any concerns you may have and also very friendly
very well located and close to the beaches
place was great close proximity to the beach
it was a great place to stay close to clearwater beach
the home was clean and great location about 10 minutes from major highways stores and beaches
Read more reviews

8. Luxurious home with gym and sauna

Step into luxury in this historic Harbor Oaks retreat, featuring a year-round swimming pool as its crowning glory. Enclosed in a tranquil outdoor setting, this pool offers heated bliss, along with the joy of poolside toys and accessories.

Beyond aquatic fun, this executive house encompasses a wealth of amenities. From the gourmet grill and outdoor fireplace to the ninja course and trampoline, endless entertainment is guaranteed. The residence also comes equipped with an accommodating gym and sauna.

Stayed at this property?
Clearwater, Florida, United States
3.01 km (1.9 mi) from Crest Lake Park
5 reviews   Wifi Available
ENTIRE HOME 3 Beds 6 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 6

Top guest reviews
Amenities & Room:
very clean comfortable furniture throughout the cozy home
so peaceful clean and comfortable
the host was very thoughtful
joana was a fantastic host:)
who does that on a beach vacation? loved the house loved the host loved everything
joana was amazing from booking through to check-out her responses were quick kind and professional
joana was very nice and responsive
beautifully renovated bungalow close to everything
Read more reviews

Enjoy private pool getaways in Clearwater

Discover the pleasure of a private pool getaway in Clearwater. Revel in accommodations that offer tranquil seclusion, coupled with the indulgence of a private pool. Whether it’s lounging poolside with a book or taking a refreshing dip, these lodgings provide the perfect blend of relaxation and luxury in this charming city.

Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.


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Leizle grew up in Dumaguete City, the City of Gentle People. This place shaped her into who she is today, especially as a travel writer. She started writing blogs and articles in 2015, and since...Read more

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