Holiday rentals with a pool in Hillsborough County

A modern kitchen area is seen with sleek cabinetry and a stylish gray sofa. The space features a silver dining table, a television mounted on the wall, and a large window revealing a private pool just outside. Fresh flowers add a touch of color.

4.89 out of 5 average rating, 288 reviews

Downtown Tampa Pool House! Walk to Armature Works!

Location! Location! Enjoy Tampa at this modern brand new remodeled POOL HOUSE with the BEST LOCATION & with POOL access! SAFE & EASY location in downtown. Come Experience events, food, festivals & nightlife only 1 block from #1 destination, Armature Works- a famous destination for food, fine dining, events, & fun! Enjoy a quiet downtown getaway to enjoy the pool, biking, paddle board or walk the beautiful Riverwalk.Full kitchen! (* We had NO Damage from Hurricane and home is Not in Flood Zone).

A serene outdoor space features a sparkling pool framed by lush tropical landscaping. A relaxing spa is integrated into the pool area, accompanied by comfortable lounge chairs. A shaded cabana and grilling station are visible in the background, enhancing the inviting ambiance.

4.94 out of 5 average rating, 117 reviews

The Jungalow SOHO - Pool/Hot Tub

The Jungalow is the ultimate urban oasis. Enjoy the luxuries of the home or venture out to local attractions like the iconic Bayshore Boulevard, Historic Hyde Park, SOHO, Downtown and more. This home was designed with comfort and convenience in mind. Fully equipped with a smart tv, high-speed WIFI, pool and hot tub - this place is paradise. Central to the action - walk to unique rooftop bars, restaurants and shops or Uber to local attractions like Water Street, Amalie Arena, and the Riverwalk.

A serene outdoor space features a large swimming pool surrounded by lounge chairs. A covered area can be seen in the background, offering seating and a barbecue setup. The pool area is illuminated with soft lighting, creating an inviting atmosphere.

4.98 out of 5 average rating, 192 reviews

The T and C Club

Welcome to The T and C Club! A featured home for the Make-A-Wish Foundation. Located 6 miles from the Tampa Airport, 7 miles from Raymond James Stadium and only 15 miles from award winning Clearwater Beach, this home is convenient as it gets. Completely refurbished, there is plenty of space to sleep 10 individuals comfortably, dining table for 10, a large resort-like backyard, saltwater pool, propane grill and all the fun you can imagine. This will truly be a case of you won’t want to leave!

4.98 out of 5 average rating, 169 reviews

Home in St. Petersburg

The Blue Fin, 3 Bed/ Heated Pool/ XBOX

Kick back and relax in this calm, stylish beach-vibin home. The 2 bedroom plus queen size sleeper sofa in sunroom is the perfect spot to get away and never have to leave. Enjoy your morning coffee or afternoon cocktail lounging by the fire pit. Light up the grill and cook your meal while you enjoy a pool heated to 86 degrees for free! Wifi and 3 streaming TV's. If you want to get out and explore, you are only 6 minutes from the award winning beaches and 25 minutes from downtown St Pete.

4.98 out of 5 average rating, 292 reviews

An outdoor space is illuminated by sunlight, featuring a heated pool surrounded by comfortable lounge chairs. A new hot tub occupies a corner, while a cozy seating area provides a space for relaxation. A screened enclosure maintains a pleasant atmosphere.

Home in Largo

TIKI Bar+SAUNA+HOT Tub+Heated POOL! 2 KING beds!

If you like pops of color, modern decor a FREE HEATED pool seasonally Oct 15-April 15 (80-85 degrees) HOT TUB , RARE SAUNA, TIKI BAR fire pit and everything new then this house is for you! BRAND NEW HOT TUB installed 4/2025!!! Very Close to shopping and beaches perfect dedicated vacation home! We are family owned and operated and dedicated to you and your vacation experience. Message me if you have any questions! SUPER FAST WIFI 753Mbps - (1 G if you plug into modem) verified by Airbnb

5 out of 5 average rating, 202 reviews

A private backyard features a custom-made pool surrounded by a wooden deck. Lounge chairs and a sun umbrella are positioned nearby, while palm trees and lush greenery offer a tropical ambiance. A white privacy fence encloses the space, enhancing the serenity.

Home in St. Petersburg

Beautiful Tampa Bay Pool Home Near Gulf Beaches

A beautiful Gulf Coast residence with many amenities to offer. Bright and open furnished spaces, for relaxing and entertaining up to 10 guests. A quiet, upscale neighborhood , your just 6 minutes from Madeira Beach and many other Gulf of Mexico beaches. Or, fun & sun in the private pool outback. 20 minutes from Downtown St Pete, which offers restaurants, museums, the new Pier, and excellent night life. Very close to countless restaurants, shopping, coffee shops, and grocery stores.

4.83 out of 5 average rating, 229 reviews

Single Family Pool Home, Close to Downtown Tampa!

Cypress House is conveniently located to explore the best of Tampa Bay, including Downtown, South Tampa, USF, University of Tampa, other Universities, Busch Gardens, the zoo, aquarium, restaurants, walking distance to University Of Tampa and River Walk, & much more! Situated in an upmarket family-friendly residential neighborhood, this 3 bed/4 full bath luxury single-story home boasts a large outdoor pool, outdoor gas grill, outdoor table, laundry, full kitchen gas stove and oven.

4.98 out of 5 average rating, 104 reviews

Bungalow in Tampa

Luxury Stay • Hot Tub & Heated Pool • Fenced Yard!

Explore the charm of this three-bedroom, two-bathroom bungalow – a luxurious haven where style meets relaxation. Enjoy moments of tranquility by the spa and screened pool, complete with inviting swim-up barstools, or unwind in the indulgent hot tub accommodating up to eight guests. Step into the serene outdoor oasis, adorned with elegant furnishings against the picturesque backdrop of a fenced backyard. Your getaway awaits, conveniently situated near the city's premier attractions.

4.76 out of 5 average rating, 134 reviews

Walk to Raymond James Stadium! Pool/ Hot Tub Home!

Enjoy this stylish and charming Tampa home with fun outdoor vibes and a pool to relax in. This home is centrally located and within minutes from Downtown Tampa, Hyde Park, Harbour Island, International Mall, Ybor City, etc. This is the perfect home to stay in for a Bucs game, as it is within walking distance to the stadium! IMPORTANT TO NOTE: This home has a detached 1/1 guest house located on the property, which may also be occupied by guests during your stay.

A spacious outdoor area showcases a heated saltwater pool surrounded by lounge chairs and shaded seating under a bright parasol. The tranquil space is framed by lush greenery and features large sliding glass doors leading into the home.

4.95 out of 5 average rating, 142 reviews

Private Oasis w/ Heated Pool and Arcade!

-9FT DEEP *HEATED* SALTWATER POOL ($25 / day) AT 85 DEGREES UPON REQUEST -COMMERCIAL ARCADE WITH >4500 GAMES 4 PLAYERS! -NBA JAM, GOLDEN TEE, THE SIMPSONS, NFL BLITZ, MUCH MORE! -MASTER KING BEDROOM -FULLY FENCED BACKYARD -OUTDOOR FIRE PIT -Propane Grill Stay comfortably in this quiet, 4/3 pool home, with a commercial family arcade! Enjoy a staycation at this tastefully updated home or take a quick ride to one of the many local Tampa area attractions!

A heated pool is enclosed by a screened lanai, featuring a unique shape with a brick border. Lounge seating is present around the pool, while a hammock is visible in the background. The tranquil area is surrounded by high wooden fencing for privacy.

4.91 out of 5 average rating, 229 reviews

Rooms with a Pool

Welcome to Tampa Bay! The home is central to everything Tampa Bay and is 1 hour 20 minutes from Orlando. This home includes a three guest rooms, 1.5 bathrooms, a living and a family room, kitchen, dining room, bar, office and a backyard lanai with a large heated pool area. You get the entire home and there is nobody else staying at the same time. It is in a quiet suburban neighborhood, about 40 minutes from downtown Tampa, Clearwater, and St. Petersburg.