
Holiday rentals with a pool in Whitfield
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Top-rated rentals with a pool in Whitfield
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.
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Popular amenities for Whitfield rentals with a pool
House rentals with a pool

Golf Course Front Oasis! Pool! Spa! Games!
We had a great stay! The location was perfect—just a short 15-minute drive to all the main attractions in Sarasota like St. Armands Circle, Lido Beach, and downtown. Having a car definitely made things more convenient than relying on Uber. The home was clean and comfortable, and we really enjoyed relaxing by the pool. It’s in a private community, which added a nice sense of security and quiet. Would definitely recommend for anyone looking to explore Sarasota! The hosts were always extremely responsive and were able to accommodate all of our requests.

“Enfuego!”
Such a perfect escape for a family or a group of friends! The backyard feels like you’re in a private tropical paradise. There are so many amenities in this home you barely need to leave! On days you want to hit the beach, it’s only about 10-15 minutes to get to Anna Maria Island - very convenient location. This was one of our favorite rentals which is well documented by all the photos we took throughout the home - swimming in the pristine pool with the waterfall and fire features glowing, playing golf, watching movies in the theatre, sun bathing on the real sand beach with tiki hut, beautiful loungers and so much more! We already have ideas about the different groups of friends we want to share this property with! Such a score and the hosts are delightful too!!

Backyard Oasis, Dual Master suite, Pool home!
We had a fantastic stay at Kara’s place. So much room to hang out for the 4 of us. The outdoor patio and pool area were a great place to hang out at the end of the day. We had access to the grill which worked out great. There was a washer AND dryer for laundry. Living room and kitchen was a great hang out place. We had such a great time !

Bayshore Gardens / free heated pool/ near beaches
We had a great stay at this Airbnb! The host was very responsive and helpful whenever we had questions. The house was clean, comfortable, and stocked with thoughtful extras like shampoo, spices, beach toys, and chairs, which made our vacation even easier. The heated pool, while a bit dated, worked well and kept us happy all week. The location was excellent — close to beautiful beaches and plenty of restaurants. The neighborhood felt safe and overall was very nice. There were a few minor issues: the pool light was broken, one chair was too damaged to use, and we didn’t have a rulebook, which made understanding the trash schedule and checkout routine a little tricky. Still, none of these small things took away from our experience. We truly enjoyed our time there and would definitely stay again!

The Sea Hut
From the moment I arrived, the home was spotless and thoughtfully prepared. The kitchen is fully equipped with a coffee maker, air fryer, refrigerator, stove, cooking pots, dishes, utensils, and dish soap. The bathrooms had hand soap and toilet paper, and the laundry area included a washer, dryer, and detergent. Beach gear such as chairs and an umbrella were also provided. As a Doctor of Pharmacy student, I truly appreciated that the university is only about 12 minutes away. I spent many days studying, but also took time to enjoy the warm Florida weather and relaxing atmosphere. The host was incredibly responsive and helpful—always quick to reply whenever I had a question. I also had the chance to play pickleball and enjoy some fun outdoor moments with my husband. The neighborhood is quiet, the house is in a gated community, and I felt very safe from the day I arrived. The cleanliness throughout the home was impeccable, and I’m genuinely grateful for the entire experience.

Bradenton Coastal Bungalow New Heated Pool!
My family and I had a great vacation at Alaura’s place. The house was not only close to the Sarasota Airport but also only 30mins to two of our favorite beaches (Siesta and Coquina beach). Alaura was very responsive, attentive, and flexible. 10/10 recommend and would also consider renting the home for future vacations.

Sara Bay Retreat
It was a great location! Nice view outback. The pool and hot tub were wonderful! The grandkids loved the pool and hot tub! The inside was spacious! We had a great time!

Private Pool Home. Close to Beaches. Pet Friendly
Todo genial de verdad muy cogedor el lugar recomendado 5 estrellas
Condo rentals with a pool

LIDO KEY 1 BR/1Bath Heated Pool 16
Had a great stay and everything was as listed. Clean and convient, quiet location, 5 minute walk to the beach. Was located right across from both pool and laundry room (quarters only) which was great. William also provided beach chairs and umbrella as well as small cooler which was exactly what I needed

A&A's Paradise near IMG & Anna Maria beaches
This was the most clean, most relaxing, most safe feeling place we've ever stayed in through Airbnb!! Thank you so much for such a wonderful experience. We would recommend 10/10 to anyone!!!!

6 min to Siesta Beach | Heated Pool | Lake View
Doris's AirBnB was exactly as listed. It was very clean. The neighborhood was quiet. It was in the perfect location. We had no problems at all. I would definitely book again.

Cozy 2 bed/2.5 bath townhome
Emily went above and beyond what I expected. I needed a cooler to go to the beach, and she also provided us with beach chairs. The house has everything you could need. There are board games. The Wi-Fi works great. I didn't use the kitchen, but it's fully equipped. I'll be back soon. Thank you so much, Emily, for your kindness and prompt response 😊

Charming and Updated 1 Bedroom in Runaway Bay
My fiancé and I really enjoyed our stay at David’s place in Bradenton! The space was super clean and had everything I needed for a comfortable stay. Communication was excellent throughout; the host was responsive, helpful, and always timely with their messages. One of the best parts was the beach access—super convenient, and the place was stocked with everything from a beach cart, umbrellas, chairs, and beach towels etc. which made days at the beach so easy. There were also a few great local tips provided, which I definitely took advantage of. Honestly, I wouldn’t change a thing. I’d absolutely stay here again and highly recommend it to anyone visiting the area. Thank you for a wonderful stay!

The Seabreeze Cottage with peaceful water views
Dear Angela, Thank you so much for hosting us! We absolutely love your decor every detail was so thoughtfully done and made the space feel cozy and "beachy". We truly enjoyed our stay and appreciated how comfortable and well-kept everything was. Hope to visit again someday. All the best. Jianfeng & Yangqing

Siesta Key Beach Front Condo
Another wonderful trip to Siesta! This is our third stay in one of Evan’s places, and we were not disappointed. This unit had a great view of the Gulf (this particular building has the most direct view, without the parking lot!), and the screened in lanai was amazing! As always, the unit was clean, well-stocked, and a perfect home away from home. Already counting down the days till we return!

Condo with a View 1: Beachfront!
This condo was everything I needed and more! The location? Absolutely perfect—the beach is literally your backyard. Waking up to that ocean view the next morning was a dream. Restaurants and activities were just minutes away, which made everything so easy and fun. Heidi, the host, went above and beyond. Her communication was fast, kind, and incredibly thoughtful. She even surprised us with a delicious key lime pie and orange juice waiting for us after jet skiing—such a sweet and personal touch! I truly have no complaints. Everything about this stay was peaceful, beautiful, and seamless. I’d absolutely recommend this spot to anyone looking for a relaxing and magical beach getaway. 🌴🌊💛
Quick stats about holiday rentals with a pool in Whitfield
Total rentals
110 properties
Nightly prices starting at
$50 NZD before taxes and fees
Total number of reviews
4K reviews
Family-friendly rentals
70 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with dedicated workspaces
80 properties have a dedicated workspace
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- Anna Maria Island
- Siesta Beach
- Anna Maria Public Beach
- Dunedin Beach
- Crescent Beach
- John's Pass
- Turtle Beach
- Caspersen Beach
- Bean Point Beach
- Raymond James Stadium
- Busch Gardens Tampa Bay
- Cortez Beach
- Lido Key Beach
- Amalie Arena
- Coquina Beach
- Gulfport Beach Recreation Area
- North Beach
- Fort De Soto Park
- Manasota Key Beach
- Vinoy Park
- Jannus Live
- Streamsong Resort
- Tampa Theatre
- ZooTampa at Lowry Park