Vacation rentals with a pool in Greater Carrollwood

4.96 out of 5 average rating, 177 reviews

The expansive saltwater pool is enclosed by a screen, presenting a clear view of the inviting water. Comfortable lounge chairs are arranged around the pool, and a cozy seating area is visible in the background, providing options for relaxation under the blue sky.

Home in St. Petersburg

Fabulous 5BR/3BA home HUGE POOL & Poolside Cabana

JamieRating, 5 stars1 week ago

We had the perfect stay at this Airbnb for our bachelorette weekend! The location was ideal—just a short drive to the beach, and close enough to uber downtown. The home was nicely decorated, clean, spacious, and had everything we needed to feel comfortable and relaxed. The pool was an added bonus that we enjoyed. The hosts were incredibly responsive and helpful from start to finish, which made the whole experience perfect. Couldn’t have asked for a better place—highly recommend!

4.98 out of 5 average rating, 114 reviews

Home in Largo

Sunny Family Paradise, Heated Pool, Hot Tub & King

JillianRating, 5 stars1 week ago

Home is beautiful just like the photos! Pool & backyard definitely the highlight of the house! We could hang there all day. Location was perfect for everything that we wanted to do. Park behind the house we all had a great time at, nice added amenity. We loved our time here and hope to be back! ☀️☀️

4.83 out of 5 average rating, 115 reviews

A spacious pool area is enclosed by a screened setting, illuminated by gentle lighting that casts a soft glow on the water. Lounge chairs frame the pool, with a blue umbrella positioned nearby. Tropical plants can be seen beyond the enclosure, providing a serene backdrop.

Home in Beach Park

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

SebastianRating, 5 stars5 days ago

This house was exactly what we were looking for to celebrate a birthday with a group of 12. The house has plenty of room and plenty of places for a big crowd to sleep. The area is absolutely stunning. Would certainly book again.

4.94 out of 5 average rating, 116 reviews

A balcony view features a decorative string of shells and a sign reading 'The Beach.' In the background, well-maintained landscaping and a sparkling swimming pool are visible, with a two-story condo complex providing a pleasant backdrop under a clear blue sky.

Condo in Clearwater

POOL VIEW IN A MODERN CONDO - Feel at Home

SusanRating, 5 stars3 months ago

The condo was great. Impeccably clean and provided everything you might need during your stay. It was excellent value for the rate. It was also a very short and simple drive to get to Clearwater beach. I would definitely go back.

4.97 out of 5 average rating, 143 reviews

A screened-in private pool surrounded by a spacious deck is visible, featuring colorful floatation rings resting on the water. Comfortable seating areas are arranged nearby, with overhead lighting softly illuminating the space. Lush greenery can be seen in the background, enhancing the serene atmosphere.

Home in Palm Harbor

Tropical Getaway w/Heated Pool & King Beds

JamesRating, 5 stars1 week ago

Extremely well equipped villa in a central location with a beautiful pool area which was lovely and private. Michelle and Evan were extremely accommodating and were only a message away if we needed anything. Will definitely be returning and would highly recommend to others.

4.95 out of 5 average rating, 164 reviews

Home in Crystal Beach

*Family Paradise with Pool in Crystal Beach*

BrianRating, 5 stars3 weeks ago

We really liked the setup. Grandma and grandpa liked the privacy occupying the smaller adjacent living area. the grandkids could come over often but when it was time, we could send them back by their parents in the larger section. We liked having the swimming area on the first floor which made it easy to prevent the kids from sneaking down. If we kept them off the deck unsupervised, they would not have to worry about pool safety. The 6 grandkids had a blast playing in the pool and hot tub. The kitchen facilities allowed us to cook most of our meals in house. The families enjoyed the nearby beaches and other activities. All in all, everyone agreed that we had one of the best family vacations ever and that this Airbnb was fantastic. Brian and Jane Smith

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What guests are saying

!Heated POOL-Near BEACH/LAKE/Downtown/WATER PARK!

4.91 out of 5 average rating, 58 reviews1 month ago

The house was a perfect fit for our getaway. It was in excellent shape and very thoroughly cleaned. The hosts were extremely responsive and helpful when we reached out with any questions. The property was amazing and the pool was very nice and clean as well. The amenities were a great bonus and we appreciated all of them (beach towels, grill, pool). We will definitely be back, it was a beautiful house in a very nice area.

Home in Largo

What guests are saying

Spacious Poolside Beach Getaway

4.94 out of 5 average rating, 50 reviews2 weeks ago

The host did an excellent job with communication and responsiveness. The house was clean and for the most part, was as expected from photographs. The playground in the backyard was a huge hit for our kids and the pool was clean and great. We enjoyed the all seasons room. This was a great stay and would recommend!

Home in Largo

What guests are saying

Largo Home with Tropical setting and heated pool

4.92 out of 5 average rating, 52 reviews9 months ago

We had a fantastic stay! The host was incredibly communicative and flexible, making our trip smooth and stress-free. The home was fully stocked with all the necessities, including beach chairs and umbrellas, which was a plus. The beds were comfy, ensuring a good night’s rest. We spent most of our days at the beach, but it was wonderful to come back and enjoy the pool in the evenings. The location was equally convenient to Clearwater, Indian Rocks, and Madeira beaches.

Home in Largo

What guests are saying

NEW! Resort Style 5bed/2bath home with pool

4.93 out of 5 average rating, 41 reviews5 days ago

We had an awesome spring break at Ari’s place! Very responsive host, kind, and helpful! House was perfect! Pool was incredible for the kids along with the rest of the backyard! Lots of memories made playing pool and roasting marshmallows ! Looking forward to our next trip down to Florida, will definitely look for this place or another one of his properties!

Home in Thonotosassa

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Popular amenities for Greater Carrollwood rentals with a pool

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House rentals with a pool

4.89 out of 5 average rating, 149 reviews

An aerial view captures a spacious backyard featuring a rectangular pool surrounded by lounge chairs. The property is framed by green lawns and trees, with a covered patio area visible nearby. The home is situated in a quiet cul-de-sac.

Home in Tampa

Pool Oasis | Karaoke | 5G | Theater 135" | Grill

NiaghaRating, 5 stars1 week ago

Everything was just like the listing stated. Easy access to everything and plenty to do in the house itself. Its funny but they have notes posted around the house with different instructions or just to let you what light switches you are using. Only problem I had, I couldnt beat PAC MAN!!!!!! WOULD definitely recommend!!

4.96 out of 5 average rating, 50 reviews

A screened-in pool area features a clear, inviting pool surrounded by a spacious deck. Lounge chairs are positioned nearby for relaxation, with partial shade provided by an umbrella. Lush greenery is visible in the background, adding to the serene outdoor setting.

Home in Tampa

Upscale Tampa Dream Home Pool, Golf, Pool Table

JustineRating, 5 stars1 week ago

We had an awesome time at Angels place. The kids LOVED the pool and the backyard was an awesome place to hang. Everything was super clean! The one queen bed was comfortable but the other beds are pretty firm (my kids didn’t mind). Other than that, no complaints and Angel was helpful and responsive!

5 out of 5 average rating, 5 reviews

Home in Largo

Oasis in Largo. Beautiful pool house, hot tub.

PeggyRating, 5 stars2 weeks ago

We loved staying at Nga’s place. Sophia who we had to contact with any issues was amazing. We ran into a few problems in the beginning but she was quick to respond and take care of it. The pool was very nice. The canal really behind the house was my husband’s favorite place to relax. A lot of wildlife which he really enjoyed. The neighborhood was quiet and neighbors were very friendly. I loved the screen in porch with a tv. We definitely would stay again if we came back in this area. I can’t say enough about how great Sophia was. You can’t go wrong renting this place.

4.93 out of 5 average rating, 94 reviews

An outdoor area features a heated saltwater pool surrounded by sun loungers on a green lawn. The space includes various patio furniture, such as umbrellas and chairs, with potted plants in the foreground. A peaceful atmosphere invites relaxation.

Home in Clearwater

Heated pool-Hot tub-Close to Beaches-Pet Friendly

KerryRating, 5 stars1 week ago

This was our first time using airbnb. House was just as described. Loved the pool and hot tub. Location of the home was close to everything from beaches to resturants and stores. Neighborhood was very quiet . We would def stay here again.

4.93 out of 5 average rating, 102 reviews

A refreshing pool area is enclosed by a screen, featuring clear blue water and two colorful inflatable loungers. Sunlight filters through, and two lounge chairs are positioned nearby, offering an inviting space for relaxation.

Home in Brandon

Relaxing 3BR/2BA POOL Home w. Pond View & HOT TUB

EmilyRating, 5 stars3 weeks ago

My family and I had an amazing time here lots of places to drive to nearby. Even if you just want to stay in the house there is plenty to do whether it’s fishing at the nearby pond or chillin poolside and hot tub at night. We had fun playing pool and playing card games with the family at night. Hose was super friendly and responsive to any questions we had. The beds were also super comfortable which is a huge plus for me. I would definitely come back here again!

5 out of 5 average rating, 35 reviews

Home in Palm Harbor

Beautiful house with pool, fire pit, billiard room

NatalieRating, 5 stars1 month ago

It’s the little things that mean a lot. There were Kleenex boxes in each room. They provided ample storage containers for leftovers. Plenty of inflatables were available for floating. Super bonus is the Florida State park pass. It’s all in the details!

4.92 out of 5 average rating, 12 reviews

The exterior of a single-story house is visible, featuring a welcoming entrance with large windows and a landscaped front yard. Lush greenery, including palm trees and vibrant flowers, decorates the area. A two-car garage is seen on the left side, complemented by a concrete driveway.

Home in Brandon

Spacious House w/ Pool & Hot Tub near Tampa

AmandaRating, 5 stars3 weeks ago

Enjoyed our stay, we used the pool and hot tub. It worked out great. Plenty of space to hang out and enjoy yourself when you’re not out doing. All the dishes and pans were easily found to cook at the house, that was excellent for us

4.83 out of 5 average rating, 101 reviews

A screened-in area features a heated pool surrounded by a spacious deck. Lounge chairs and tables are arranged nearby for relaxation. Sunlight reflects off the clear water, creating a tranquil atmosphere. The exterior walls offer a neutral tone, enhancing the overall brightness of the space.

Home in Tampa

4BR Heated Pool Relaxation Home | Airport | Beach

KateRating, 5 stars1 week ago

The house was amazing! Very clean and a perfect location. A quiet neighborhood but not too far from anything. Communication with Mark was great and he was a great help with everything we needed. We will definitely be back should we find ourselves in Tampa again!

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Condo rentals with a pool

4.97 out of 5 average rating, 120 reviews

A spacious living area features a light beige sectional sofa paired with a glass coffee table. A large flat-screen television is positioned near a potted plant. Bright turquoise and soft yellow walls complement the cozy atmosphere, while a ceiling fan provides comfort.

Condo in Clearwater

Key West Retreat, 2 Bdrm, A+ Pool, 2.9 mi to Beach

DebraRating, 5 stars3 weeks ago

We recently spent a month in this beautiful condo. We loved the beach vibe, beautiful bright colors, and cute decor. The apartment was very clean and well equipped with everything you could possibly need. Brendan and Becky were spot on with recommendations of local attractions, restaurants, and their favorite places to visit. We definitely would stay here again!

4.81 out of 5 average rating, 110 reviews

A spacious, heated swimming pool is surrounded by palm trees and lounge chairs in a sunlit environment. Several guests enjoy the water, while the condominium buildings provide a backdrop. The area is designed for relaxation, featuring a well-maintained pool deck and scenic landscaping.

Condo in Clearwater

Seaside Paradise at Clearwater - Resort Style

StephanieRating, 5 stars1 month ago

It was a very nice place to stay, people were friendly, the pool was great! The layout of the condo was perfect and the place was clean! I definitely recommend this place to stay!

4.97 out of 5 average rating, 148 reviews

A view from the balcony reveals a refreshing pool surrounded by palm trees and umbrellas. The water glimmers under bright sunlight, with the bay visible in the background. The area features manicured landscaping and a paved parking space.

Condo in Tampa

Tiki Themed Waterfront Condo on Tampa Bay

PatriceRating, 5 stars3 days ago

Chris was very helpful and proactive through messages and short videos. Made everything easy. Would definitely stay again.

4.97 out of 5 average rating, 145 reviews

A large, heated pool is surrounded by lounge chairs and tropical palm trees. The bright yellow buildings of the complex provide a cheerful backdrop, complementing the clear blue sky. The pool area is well-maintained, offering inviting space for relaxation.

Condo in Seminole

SUNNY DELIGHT! HEATED POOL 2 miles to the beach🐶

DonaRating, 5 stars1 month ago

Sandra's Place was EVERYTHING thats in the posting. She has everything there for you in case u missed something while packing. The place feels like its urs, furnished well, felt like home. Thanks Sandra

4.8 out of 5 average rating, 114 reviews

A living room features a comfortable sectional sofa positioned beside a glass coffee table. Natural light enters through large windows, illuminating a cozy reading area with a rocking chair. The walls display a colorful piece of artwork, and a ceiling fan enhances the airy atmosphere.

Condo in New Tampa

Beautiful and spacious condo centrally located

MiguelRating, 5 stars5 days ago

Alexandra’s place was perfect—clean, cozy, and exactly as described. The location was great. Highly recommend staying here!

4.98 out of 5 average rating, 211 reviews

The pool area is illuminated under the night sky, reflecting soft light from surrounding palm trees and buildings. Features include a clear blue water surface and poolside seating. Soft lighting enhances the relaxing ambiance of the resort-style community.

Condo in Tampa

PondView/Pool/Pickleball/Dryer/Washer/Ground Floor

CarolineRating, 5 stars4 days ago

Great place to stay for our trip to watch the Tropical Sevens. Place was tidy and well equipped with everything we needed and more. Responsive host! Would stay again!

4.8 out of 5 average rating, 133 reviews

A modern living area features a light-colored sofa and dark accent chairs arranged around a central ottoman. A wall clock complements the artwork displayed above the couch, while the kitchen area is visible in the background, showcasing sleek cabinetry and appliances.

Condo in Paradise Lakes

Millers, BeOne Naturally Clothing Optional Premium

BrianaRating, 5 stars1 week ago

Small but nicely updated unit. Great for two for an extended weekend. Jimmy was a very accommodating host, making us feel very welcome. He provided a great tour of the property and checked in with us throughout our stay. Also the complimentary golf cart was a very nice touch. Will be back for sure.