Holiday rentals with a pool in Pinellas County

4.98 out of 5 average rating, 126 reviews

A spacious backyard is featured, showcasing a heated saltwater pool surrounded by a large paver deck. Lush green grass fills the area, bordered by well-maintained landscaping. Tall trees provide shade in the background, contributing to the serene outdoor environment.

Home in Seminole

JOJO'S Beachside 1Acre Estate-New Pool

LUXURY CUSTOM HOME WITH NEW HEATED SALTWATER POOL ONLY 1.5 MILES TO BEAUTIFUL WHITE SAND REDINGTON BEACH ON 1 ACRE OF LAND. HOME HAS JUST BEEN TOTALLY RENOVATED WITH TASTEFUL FINISHES. THIS AREA IS VERY QUIET AND UNIQUE FOR PINELLAS COUNTY WITH LARGER LOTS AND HOMES. 2300 SQUARE FEET WITH HIGH VAULTED CEILINGS. LARGE OPEN KITCHEN, T.V.'S IN EVERY RROM. GREAT LOCATION JUST MINUTES FROM: COFFEE SHOPS , GROCERY STORE, SHOPPING, RESTAURANTS, MOVIE THEATERS AND PARKS. LARGE PAVER DECK BY POOL AREA.

A covered patio area is visible, featuring comfortable wooden chairs with blue cushions and a wooden table. The scene is framed by a screened enclosure, providing an unobstructed view of a private pool surrounded by lush tropical plants.

4.89 out of 5 average rating, 302 reviews

Quiet 3 BD Large Heated Pool & Terrasse-5 mn Beach

Unwind and relax while staying at our freshly renovated Floridian nest! Pretend you are lost in our tropical garden while diving in the pool, take some time for yourself on the covered patio directly facing the blue water and the vivid green of the palm trees. Just breathe, your favorite meal smells good on the grill and your family is enjoying the large TV in the comfortable open space with high ceilings! Enjoy the sea, you are a 5 min drive from the beach and close to everything. Feels good!

4.91 out of 5 average rating, 196 reviews

The Oasis - Arcades - Golf & Games - HTD Pool

Staying at The Oasis is the perfect blend of vacation and home. Every detail was carefully thought out to provide guests two things: comfort and fun. The ULTIMATE vacation awaits you. Whether a group of friends or your family vacation, this home was designed with relaxation AND fun in mind. Located within walking distance to Largo’s beautiful Central Park and a few miles to the beach, you can spend the day exploring the area or truly relax in the resort style, private backyard. BUT! No parties

The inviting pool area features a heated pool with clear turquoise water, surrounded by lounge chairs and a spacious pool deck. A dining area and outdoor kitchen can be seen, with a large TV mounted on the wall, creating a welcoming space for relaxation and entertainment.

4.97 out of 5 average rating, 179 reviews

Palm Oasis | Heated Pool | Near Beaches

Have fun with the family or just a friend getaway at this stylish cozy POOL home. This newly remodeled 3-bedroom 2-bath home, centrally located between Clearwater and St. Petersburg and a 30 min drive to Tampa to visit all the local attractions. Very close to plenty of restaurants, shopping, and Beaches. This home has everything needed from quality mattresses to kitchen essentials and “Smart TV’s” in every room, very close to shopping, restaurants, movies, Walmart, etc. “Must be 21 to book”.

4.9 out of 5 average rating, 478 reviews

A set of two white wicker chairs and a small table are positioned on a balcony, providing views of the Gulf of Mexico. The ocean and sandy beach stretch into the distance, with clear blue skies overhead.

Apartment in Clearwater

Amazing views on beachfront

This spacious upper-floor, 3-bedroom condo hotel suite offers views of the Gulf of Mexico from your private balconies. While preparing your morning coffee on the spacious kitchen island, you can see the water of the Gulf of Mexico. Each suite can accommodate 10 people, with 3 bedrooms, 2 of them with a King bed in each bedroom and the third with 2 Queen beds, each of them with their own ensuite bathroom, in total 3 1/2 bathrooms, also a comfortable full-sized sofa bed in the living room.

5 out of 5 average rating, 225 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.

4.98 out of 5 average rating, 115 reviews

A private heated pool is surrounded by wooden decking, offering lounge chairs for relaxation. An oversized umbrella provides shade, while tropical plants enhance the outdoor space. The rear of the house is visible, along with a patio door leading into the home.

Home in St. Petersburg

ST Urban Oasis heated pool

Located in unincorporated St. Pete, you can keep it simple at this peaceful and centrally-located oasis. Want to be near the city and beaches while having your own private backyard sanctuary? This is your place to enjoy it all. This home features two bedrooms, one bathroom, and a private heated pool. The backyard has been filled with beautiful large palms, bamboo, and other zen features to allow you and your family to enjoy a relaxing and easily accessible stay in beautiful St. Pete.

4.98 out of 5 average rating, 231 reviews

Home in Clearwater

Specious home W/ Heated Pool ! ! ! Great Location.

Cozy, spacious home 🏡 w/ heated swimming 🏊‍♀️ pool, next to a golf ⛳️ course. Close to the famous beaches ⛱️, St.Pete and Tampa. This cozy open home has a large living room, big kitchen and pool deck patio. All 3 bedrooms have large TV's. The big back patio has a swimming 🏊‍♀️ pool, TV, fridge and BBQ for cook outs & R&R. Located in a quiet family-friendly neighborhood. Location! 15 min - Clearwater Beach, Dunedin, Safety Harbor 30 min from - St.Pete, TPA Airport, Tampa

Apartment in Treasure Island

The exterior of the Ocean Club building is showcased, featuring a modern design with a white façade and large balconies. Palm trees line the front, enhancing the tropical setting. A welcoming entrance is visible, set against a backdrop of a bright sky with soft clouds.

4.86 out of 5 average rating, 658 reviews

Beachfront Condo in Exclusive Resort

The most stunning views from this brand new condo directly on Treasure Island Beach. This lovely unit is on the 4th, 5th, or 6th floor and provides sweeping views of the ocean. This units has 2 bedrooms and 2 full bathrooms. The inviting open concept living area has one of the best views of the ocean, especially when the retractable sliding doors are opened. The dining table on your private balcony provides a perfect dining area, with the ocean providing a beautiful backdrop.

4.93 out of 5 average rating, 163 reviews

Swim-Out Bedrooms, Waterfall pool, Peace Place

Unique tropical oasis complete with 2 swim out bedrooms, Tiki Hut and tiki bar! LGBTQIA + welcome! Hablo Español. Pet haven. Tropical Airbnb retreat! Our unique resort-style heated PRIVATE pool with waterfalls and dual sun-shelves, / in pool loungers, surrounded by lush landscaping, is a private oasis. 3 bedrooms, with Large 3rd bedroom with 2 queen beds At night the outdoor space comes alive with pool and landscape lighting! You wont want to leave the house!

4.78 out of 5 average rating, 210 reviews

A spacious saltwater pool stretches across the backyard, bordered by a paved area featuring lounge chairs. Lush greenery, including palm trees and a nearby canal, enhances the serene outdoor setting under a clear blue sky.

Villa in St. Petersburg

Dolphin Cove Waterfront St. Pete Beach w/ Pool

THIS is the Florida life! A private oasis with a stunning tropical backyard and an oversized SALTWATER pool. Enjoy 140+ ft of waterfront on Bear Creek canal, where manatees and dolphins visit daily! Kayak just 15 minutes to nearby islands. Beaches are a quick 7-minute drive, downtown is 15 minutes away, and shops/restaurants are right across the street. The home is simple and unupdated, but the backyard is a true paradise you won’t forget!

A heated pool area is surrounded by tropical plants and palm trees. A tiki hut provides shaded seating, and lounging chairs are positioned around the pool. A textured stone deck complements the inviting water of the pool, creating a relaxed atmosphere for guests.