Holiday rentals with a pool in Hillsborough County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Hillsborough County

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

0 of 0 items showing

1 of 3 pages

Guest favourite

Home

4.99 out of 5 average rating, 68 reviews

Remodeled pool cottage, just minutes from beaches

Relax by our cocktail pool in this recently remodeled guest cottage that is just minutes from the Sun Coast beaches. You will find our cottage is fully equipped and has everything you'll need for a quick getaway or an extended stay. The back door opens up to the patio and the lush, tropically landscaped backyard pool area. 5-minute drive to St Pete Beach, 7 to Treasure Island. Uber, Lyft or ride the SunRunner shuttle, and forget about the hassle and expense of beach parking. We are pet-friendly!

Guest favourite

Home

4.95 out of 5 average rating, 208 reviews

Stunning Home with TWO Pool Cabanas+Guest Bungalow

A 6 min. drive to Madeira Beach and miles and miles of beach coast. Stunning pool home with TWO poolside cabanas and a brand NEW poolside guest bungalow.HOME SLEEPS UP TO 14 GUESTS! Fully renovated home with 3 full bathrooms. Wifi and 8 smart televisions. Professionally designed and decorated home in a family neighborhood near dining, shopping, Walmart and beaches! This home is professionally and immaculately cleaned before every guest. Heated pool OPTION is available for additional cost.

Guest favourite

Home

4.86 out of 5 average rating, 104 reviews

7Beds/Pool/Grill/Billiards/Tampa/ Near Airport

This Ranch style home is in South Tampa's Beach Park community and features a large private backyard with pool. The single level home has 2928 sqft. of living space with an open floor concept that was recently renovated and equipped with all the modern amenities including hardwood flooring, granite countertops, recess lighting and more. Additional features of the home include newly installed privacy fence, outdoor kitchen, large screened pool enclosure Heated pools additional $25 per night

Guest favourite

Home

4.87 out of 5 average rating, 166 reviews

Poolside Bliss in Clearwater! Heated-pool/Spa

HEATED POOL FREE OF CHARGE Your vacation spot grants you exclusive use of a fully updated 3 bedroom and 2 bathroom home with a private pool! With 3 bedrooms, 7 beds, that sleeps 12 comfortably can accommodate up to 14. This home has an amazing spacious backyard for family gatherings and overall enjoyment of the outdoor spaces.Located 8 miles from the world famous Clearwater beach, it is in a prime location with many events happening nearby.Safely situated in a quiet desirable neighborhoods

Guest favourite

Home

4.91 out of 5 average rating, 135 reviews

Heated Pool and hot tub luxury vacation house

Spend your vacation in luxury! The hot tub and heated swimming pool are perfect for a family vacation or a couples' retreat. In winter we keep the pool temperature at 85 degrees. Enjoy the stylish furniture, a huge luxurious master suite with a large walk-in closet and work desk, a fully equipped kitchen and all the extras you would expect at the resorts. The living room features a 75’ TV! Short drive to Madeira Beach and Treasure Island. Small parties are allowed. A lot of parking space.

Guest favourite

Home

4.87 out of 5 average rating, 92 reviews

Gorgeous Home w/ Huge Salt-Water POOL & SPA

Gorgeous 5 bedroom, 3.5 bath home with huge salt-water pool and spa. Pool heating is available for an extra change. Please ask for details. Perfect for large groups. 2 bedrooms have en-suite bathrooms, one on 1st floor and one on the 2nd floor. Fantastic location - close to airport, major highways, beaches, Hyde Park for restaurants and bars, 5 min walk to BayShore Blvd. This place has everything you need for a luxury hotel-like stay! Easy access with an electronic lock.

Guest favourite

Home

4.97 out of 5 average rating, 135 reviews

Tropical Getaway w/Heated Pool & King Beds

Welcome to our “sun-kissed” get-away in beautiful, conveniently located, Palm Harbor, FL. In less than 10 minutes you can find yourself sitting on the shore of one of our award-winning white sandy beaches or teeing off at a pristine golf course, and only 30 minutes from Tampa attractions. There is plenty of space to sleep 6 very comfortably, a beautiful bird caged pool and outdoor seating/lounging, BBQ grill, and fun for everyone. Come and enjoy...you just might not want to leave!

Guest favourite

Home

4.94 out of 5 average rating, 50 reviews

Largo Home with Tropical setting and heated pool

Have fun with the whole family at this beautiful, stylish beach getaway! This home features a PRIVATE HEATED POOL situated in a tropical oasis. The home is perfectly located from multiple Top Rated Beaches in the US and many restaurant options. Clearwater beach is 7.5miles, Indian rocks beach is 6.3miles, Belleair beach with beach access from Morgan park is 5.5 miles, Madeira and Redington beach are 9 miles away. Pool floats, towels, and beach chairs provided.

Superhost

Home

4.88 out of 5 average rating, 235 reviews

Salt Water Pool&Hot Tub 4mi from Gulf Beach-slps 8

Perfect for your next FL vacation! This trendy home is equipped with full kitchen, coffee bar, ivy wall/neon sign with Polaroid photo booth for your photo ops, 3 smart TVs, indoor golf putting green, Tempur pedic mattresses, & small reading nook. Outside presents a large in ground Salt Water Pool and Hot Tub, Day bed under palm trees, Bistro set for morning coffee, &fire pit w/ high privacy fence tucked into a quiet neighborhood just 4 mi from gulf beaches!

Guest favourite

Home

4.91 out of 5 average rating, 75 reviews

Downton Blue

This home has two bedrooms and two full bathrooms. The living room is spacious with a view of the private pool. Each bedroom has a television and so does the living room. The kitchen is well equipped, and has a dishwasher. It has a fenced in yard and your pets are welcome! There is a furnished screened-in patio as well as ample seating outside around the pool. There is a charcoal grill available. There are two parking spaces available.

Superhost

Home

4.86 out of 5 average rating, 21 reviews

Exquisite Fun Getaway with Private Pool!

Step into our charming Airbnb nestled in the heart of Oldsmar, Florida, where the perfect blend of opulence and practicality awaits you in a cozy, one-story retreat. Immerse yourself in the allure of this enchanting escape, designed to provide an unparalleled experience for guests in search of tranquility, outdoor pursuits, and a sprinkle of historical allure.

Guest favourite

Home

5 out of 5 average rating, 7 reviews

(HGR) Poolside Paradise: Airbnb Retreat

Welcome to our stunning 3-bedroom home with a heated pool, covered outdoor living area, and BBQ. Enjoy a fully equipped kitchen and a game room with a pool table, dart board, and arcade machine boasting 1500 game titles. Experience ultimate relaxation and endless entertainment in our luxurious Airbnb retreat. Book now for an unforgettable getaway.