Vacation rentals with a pool in Oldsmar

An outdoor space features a heated pool enclosed by a screen. Lounge chairs are positioned nearby, surrounded by a fenced backyard with landscaping elements, including palm trees and a hammock. Sunlight reflects off the clear water, enhancing the inviting setting.

4.93 out of 5 average rating, 100 reviews

Cozy Tampa Home with Large Heated Pool

“No Cleaning Fee, No Chores” Your family will be close to everything when you stay at this centrally-located home. This home is located 5-10 mins from shopping centers, restaurants, gyms, pet and child daycares, community sport courts, local parks and hospitals. 20-30 mins from Bush Gardens, Downtown, ZooTampa, Tampa Airport, Cruise Port, Ben T Davis Beach, Raymond James Stadium, Hard Rock Casino, Hillsborough State Park and more. Only 1hr 30min from Disney, Universal, Sea World, Lego Park

A screened-in lanai features a heated saltwater pool surrounded by colorful outdoor furniture. Children’s toys and pool floats are placed nearby, alongside a small bike. The serene space is perfect for relaxation and play, with trees visible beyond the enclosure.

5 out of 5 average rating, 102 reviews

Coastal Escape: heated saltwater pool & beaches

★ Close to beaches - Honeymoon Island: just 6 miles away. - Clearwater Beach: 15 miles away - crowned the nation's #1 beach Trip Advisor in 2018 ★ Heated saltwater pool ★ Screened-in lanai ★ BBQ grill ★ Large backyard w/ playground ★ Outdoor dining area ★ 3 bedrooms New Mattresses - California king size bed - Queen size bed - Kid-friendly room w/ two bunk beds ★ Renovated kitchen and bathrooms ★ Open living space - great for family gatherings, movie nights ★ Children toys and games

Guesthouse in Palm Harbor

A private screened pool area features an oval-shaped swimming pool surrounded by a brick patio. Lounge chairs are positioned along the edge, with two bright blue chairs situated nearby. The area is illuminated by natural light filtering through the mesh enclosure.

4.97 out of 5 average rating, 309 reviews

Private Suite, 1 bedroom, 1 bathroom, pool, patio

Private suite attached to Large house located in Palm Harbor with king-size bed, Split unit A/C Amenities include: Large Bathroom with Jacuzzi, Walk-in Shower. Access to shared pool and patio, backyard and Sundeck. Room includes refrigerator/freezer, Microwave, Coffee maker, Iron and kitchenette. Bistro set in room. Private entrances to room and patio/backyard. No shared space. Cable TV, Streaming and Wi-Fi . Centrally located to Restaurants and shopping. 10 mins. to the beach/Pinellas Trail.

Guesthouse in Palm Harbor

A modern bathroom is shown featuring a sleek vanity with a rectangular sink and black fixtures. A round mirror is illuminated by three overhead lights. Storage is provided by wooden drawers beneath the sink, and towels are neatly arranged on shelves.

4.9 out of 5 average rating, 141 reviews

Home away from home

Private unit has designated parking, pool access, its own water heater, water softener, filtration system, 2 ceiling fans, heater, air purifier & a/c. Featuring a queen bed, dresser, 42” tv & fire stick w/ streaming accounts, wifi, full length mirror, recliner, eating table & chairs. The bathroom has a walk-in shower, large vanity mirror, & all the needed bathroom accessories. Full kitchenette w/ microwave, dual burner, air fryer, tea kettle, coffee maker, & more. Owner lives on property.

4.93 out of 5 average rating, 213 reviews

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.

Home in Tampa Heights

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).

4.9 out of 5 average rating, 166 reviews

The sleeping area features a cozy bed adorned with neutral-toned linens and decorative pillows. Three framed botanical prints are displayed on the wall above the bed. A bedside table with a lamp and a small potted plant is positioned next to the bed.

Apartment in Tampa

Private 1 Bed Apt with Pool and water front.

Enjoy the use of the onsite pool and Private 1-bedroom apartment in a peaceful waterfront community! Equipped with your own kitchenette and separate living area. Enjoy the serenity of swimming in your own pool on your vacation or relaxing work stay. Lounge chairs will make your stay even more relaxing. Close to the Veterans expressway and easy access to local restaurants, beaches, 10 minutes from the airport, 20 minutes from the river walk, and entertainment. This apartment is 300 square feet

The outdoor area features a heated pool with crystal-clear water, surrounded by a screened lanai. Comfortable lounge chairs are placed nearby, providing ideal spots for relaxation. Tropical plants enhance the space, framing a serene environment perfect for swimming and sunbathing.

4.91 out of 5 average rating, 112 reviews

Heated Pool, 10 min to Beach, Close to Restaurants

Welcome to Turtle House! Perfectly situated in the heart of Palm Harbor lies this gem. Enjoy a completely renovated private heated pool, and with a quick and convenient access to US19 enjoy shopping, restaurants or local beaches. Perfect for families, couples, and anyone who needs the space to spend time together or enjoy some privacy for enjoyment and relaxation. 10% discount for Military, First Responders, Teachers, friends and family - book & message me, I'll apply the discount, that's it!

A welcoming exterior view of the house, featuring a landscaped front yard with palm trees and decorative rocks. A large driveway leads to a garage, while outdoor seating is visible on a covered porch, framed by large windows and soft natural light.

4.99 out of 5 average rating, 134 reviews

Tropical Oasis Retreat w/ Heated Pool

Welcome to a Private oasis located in your very own backyard. Spend the day lounging by the heated pool, grill pit cooking your own food together with privacy fence. Master bed has ensuite bath. When you venture out, this Palm Harbor house is ideally located by Crystal Beach and bike ride to Honeymoon Island for some sparkling Gulf Coast beaches. With multiple golf spots like Innisbrook right next door and Clearwater beach just down the road, you can stay busy year-round. We are pet friendly

A shaded patio area features a seating arrangement with four black wicker chairs surrounding a low table. The table displays neatly arranged shells and a colorful beach ball is visible near the shimmering pool, surrounded by lush greenery.

4.8 out of 5 average rating, 220 reviews

3Be/2Ba Beautiful Summer House with heated pool

Welcome to your perfect getaway! Our cozy and inviting home is a haven of comfort. Enjoy modern amenities, a fully equipped kitchen, and a serene backyard with a pool – perfect for suntanning and relaxing. It's within walking distance to a great golf club, playgrounds, a sand volleyball pit, and more! Plus, it's just a 20-minute drive from top local attractions like Tampa Airport, Clearwater Beach, Tampa Zoo, and Busch Gardens. Book now and experience relaxation and adventure in one package.

4.96 out of 5 average rating, 139 reviews

Home in Dunedin

Dunedin 5 STAR! Heated POOL+10 Mins to Beach

This Modern Coastal home is the perfect vacation spot! Recently renovated 3br home located just a few minutes from downtown Dunedin and some of the best Gulf Coast beaches. Take a dip in our heated saltwater pool, or relax on the screened-in patio with a cup of coffee. The open concept design creates a relaxing atmosphere with all the necessary amenities. Conveniently located near excellent dining options, shopping, Blue Jays stadium, and the waterfront. Make unforgettable memories.

An outdoor seating area features a colorful table surrounded by white and pastel chairs. A fire pit is present nearby, with patio heaters positioned for comfort. The view overlooks a heated pool and blue umbrellas, with lounge chairs arranged around the poolside.

4.95 out of 5 average rating, 302 reviews

Modern Waterfront Condo - Captivating Sunset Views

This waterfront one bedroom condo will be your perfect place to relax and make new beautiful memories whether is for holiday or business. It has a fully equipped kitchen. Laundry and dryers are coin operated located at third floor. Guests are allowed to use resort’s common areas like heated pool, fire pit bar/ restaurant. Located near Tampa airport (TPA). Within walking distance of public beach restaurants, and Courtney Campbell trail. Resort doesn't have access to the beach.

5 out of 5 average rating, 141 reviews

The grotto pool features natural rock formations, surrounded by tropical foliage and palm trees. Two lounge chairs are positioned near the water's edge, and the pool area is framed by a white railing that complements the inviting landscape.

Home in Oldsmar

Bayside Retreat your tropical oasis

"Bayside Retreat" is a Charming Private 1~bedroom/1 bath with full living room suite, located right on the water of upper Tampa Bay. Spend a quiet day lounging in the grotto pool, kayaking the bay, or a lazy day reading in the hammock. Enjoy breath taking sunrise and sunsets from the dock. Your own Tropical Paradise away from the rest of the world....... Just 15min to Raymond James Stadium. Centrally located 15 miles from TPA Airport

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Popular amenities for Oldsmar rentals with a pool

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Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.89 out of 5 average rating, 82 reviews

An aerial view captures a spacious neighborhood with well-maintained homes and lush greenery. The property features a spacious backyard with a screened-in pool area. Surrounding trees enhance the area's natural beauty, providing a peaceful atmosphere for relaxation.

Home in Safety Harbor

Nice Sparkling Clean Home with Pool.

KalinRating, 5 stars2 weeks ago

Stayed here two years in a row, both times me and my family enjoyed every minute of our stay!

4.99 out of 5 average rating, 235 reviews

A spacious covered screened porch features a heated pool visible nearby. Lounge chairs with cushions are arranged beside the pool. A dining table with chairs is positioned on the porch, alongside a propane gas grill, all set against a backdrop of surrounding greenery.

Home in Port Richey

Heated & Screened in Pool-All Essentials Provided

TimRating, 5 stars6 days ago

Very clean and very well equipped. House was very responsive and even checked in on us mid stay to see if we needed anything! Would definitely rent again

4.91 out of 5 average rating, 104 reviews

A private swimming pool is surrounded by a screened patio, with colorful floatation devices resting on the clear water. Lounge chairs are positioned nearby against a bright yellow wall. Natural light floods the area through glass doors, creating a refreshing atmosphere.

Home in Holiday

Private Pool 2BR/2B 3.5 mi Tarpon & Beaches

JessicaRating, 5 stars1 week ago

Clean place Prompt host Many amenities in the house

5 out of 5 average rating, 161 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

PatriciaRating, 5 stars1 week ago

This Airbnb was amazing! The house was clean and well organized. Ruta thought of everything from kitchen utensils and cookware to recreational games and equipment. There were plenty of chilled waters available to us in the refrigerator as well as extras in the garage refrigerator. The rooms are very spacious. The beds are extremely comfortable and complimented by multiple choices of pillows and blankets. The pool area is very nice with clean refreshing water and an intimate setting. There is plenty of living space to spread out as well as a game room with a pro-sized pool table. There is a variety of card games and even a poker set. Additionally a pack and play is provided by the host. I would definitely book this home again and will refer it to friends and family. Ruta really thought of everything.! 🤗🎊🥳🙌🏽

An outdoor area features a private pool surrounded by a concrete deck. Lounge chairs and a dining table are visible beneath a covered patio, while tropical landscaping adds greenery. A path of stepping stones leads toward the pool, inviting relaxation and leisure.

4.94 out of 5 average rating, 64 reviews

Private pool, Golf Cart, Completely Renovated!

JamesRating, 5 stars5 days ago

This home is beautiful decorated. Comfortable. It is our 2nd time staying in 2025. We love the location. We especially love having full access to the golf cart to go to many of our favorite restaurants. The pool is beautiful. 4 of us stay here and we will return again when we are in the area. It is central to all the places we love to go. Jarrett is a great and responsive host.

4.96 out of 5 average rating, 362 reviews

A spacious living area is furnished with a large sectional sofa and additional seating, centered around a rustic coffee table. Large windows provide natural light, while a ceiling fan adds comfort. An open layout connects to a dining area and kitchen in the background.

Home in Tarpon Springs

Tarpon Fun'n Sun-Pool, Beaches + Backyard Chickens

DavidRating, 5 stars2 weeks ago

Overall our stay was great! Jeff was very responsive, and left us a lot of recommendations for local restaurants. The house was very clean and the pictures accurately reflected how to house looked. The only downsides were the large bugs that somehow got in the home. There were 3 occasions this happend but they seemed harmless. The net around the pool had a tear in it allowing spiders and lizards inside of the pool area but they stayed around the outside of the pool so we could avoid them.

A dining area is featured with a dark wooden table surrounded by four light-colored chairs. A large artwork depicting a beach scene is mounted on the wall, complemented by ambient lighting. Doorways leading to other rooms are visible, enhancing the space's openness.

4.89 out of 5 average rating, 37 reviews

your home close to everything

KellieRating, 5 stars1 week ago

Great place, pool was very nice. Rooms were nice. We stayed with our young kids and there weren’t plastic plates/ cups, but they were careful with the glassware. Fridge was very updated and nice as well as tvs in all the rooms and living room. Great lounging couch. Overall we would stay again.

A private pool is surrounded by a spacious concrete deck, featuring several lounge chairs and tropical landscaping. The clear blue water is set against a backdrop of a blue sky and a white fence, creating an inviting outdoor retreat.

4.85 out of 5 average rating, 104 reviews

Luxurious House with private Pool.

CollinRating, 5 stars3 days ago

The house was perfect for my wife, my dad, my good friend, and myself for the Metallica weekend. I have season tickets for the Bucs, but typically make the 2hr drive back home. Now we have a place to go back to for an extended trip. The pool is great! The house was clean and as advertised. If you are heading to either Raymond James Stadium or Steinbrenner Field, it's about a 15 minute drive depending on traffic. We will definitely be back.

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Condo rentals with a pool

4.99 out of 5 average rating, 100 reviews

A spacious heated pool is surrounded by lush palm trees and well-maintained landscaping. Comfortable lounge chairs are positioned along the poolside, providing ample relaxation spots. The pool area is framed by the community buildings, creating a welcoming atmosphere for guests.

Condo in Clearwater

Seasalt Breeze private cozy unit

KarlRating, 5 stars1 month ago

Beautiful, very clean condo, very clean pool. Great location only a short drive to Clearwater beach. Margaret was very responsive to our questions and was an excellent host. Would highly recommend staying at this location.

4.9 out of 5 average rating, 203 reviews

The pool area is surrounded by lush greenery, featuring a spacious, inviting pool accompanied by a hot tub. Sun loungers are neatly arranged along the deck, creating a relaxing atmosphere. The building's architecture is designed in a contemporary style, enhancing the serene environment.

Condo in Clearwater

Very cozy quality condo close to Clearwater Beach

KarenRating, 5 stars3 weeks ago

The condo was wonderful - spacious, spotless and super quiet which made for a relaxing stay. I liked having a washer and dryer, dishwasher and beach supplies. Marta was a thoughtful and responsive host who checked in on me during my stay, which I appreciated.

A sandy beach area features two wooden lounge chairs under a thatched roof, offering shade and comfort. In the background, the calm waters of Tampa Bay stretch towards the horizon, while a nearby swing set adds a playful touch to the serene environment.

4.9 out of 5 average rating, 168 reviews

Waterfront condo with sunset views of Tampa Bay.

JenniferRating, 5 stars3 weeks ago

We really enjoyed relaxing by the pool and having the Big Bamboo bar / restaurant on the premises made it so convenient. The bed was comfortable and shower pressure good. We also appreciated the coffee bar.

4.82 out of 5 average rating, 196 reviews

A clear blue swimming pool is surrounded by lounge chairs and palm trees, providing a sunny space for relaxation. Umbrellas are positioned nearby for shade. The pool area offers views of the surrounding greenery and the apartment complex in the background.

Condo in Palm Harbor

Lakeside 2- Bed Apartment Near Clearwater Beaches

BobbieRating, 5 stars6 days ago

Beautiful condo. Comfortable beds. Great restaurants near by. Beautiful beaches near by. The swimming pool was clean and the kids really enjoyed it. Would definitely stay again.

4.95 out of 5 average rating, 194 reviews

A refreshing pool is surrounded by palm trees, with clear blue water reflecting the sky. Paved stones create a smooth area around the pool, offering seating options nearby. The backdrop features a serene view of the waterway and distant clouds.

Condo in St. Petersburg

Sea La Vie- Studio by the bay!

AnnaRating, 5 stars1 month ago

I escaped MN to find this hidden gem! It was everything I could have asked for and more! I enjoyed the pool throughout my stay and catched a glimpse of a few dolphins. The bed was extremely comfortable and the unit was quiet. There was SPF and aloe in the bathroom cabinet which was perfect because I needed both! Walmart is a short uber away for all of your grocery needs. Doc’s next door was great to walk to for a quick dinner and drinks. The only hiccup I experienced was that pest control needed to enter the unit to spray and didn’t give Alison much notice so she could ensure I was out of the unit. I can’t wait to come back to this gem next year!

A tranquil view of a swimming pool is showcased against a vibrant sunset over the water. Poolside loungers are arranged along the edge, providing ample space for relaxation. The surrounding area is landscaped, with a fence framing the picturesque scene.

4.75 out of 5 average rating, 241 reviews

Rocky Point paradise

GlendaRating, 5 stars3 days ago

It was a very clean place and a great location. We were there to attend an event at Raymond James which was only a short drive, and close enough to the beach to enjoy that as well. The balcony was nice and private. We loved being able to just sit and enjoy the peaceful water view!

A poolside bar and restaurant is visible adjacent to a heated pool, surrounded by lounge chairs. The building features a modern design, with balconies overlooking the pool area. Palm trees provide shade in the background, enhancing the tropical ambiance.

4.85 out of 5 average rating, 108 reviews

262*NEW! 3 beds x 2 bath. Amazing Waterfront Views

MollyRating, 5 stars1 month ago

Great area. Great view. Awesome pool/ bar area!