
Vacation rentals with a pool in Whitfield
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Whitfield
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
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.

"Oasis Villa Retreat" Near Beaches and IMG Academy
This home was a good distance to all places me and my group ventured off to. The home was clean and Sheron was amazing at responding. Would absolutely recommend to stay here :) Thank you Sheron !!

Waterfront/Kayak with Manatees/Pool/Fish
Beautiful home with so many extras. Kayaks, coffee, shampoo. All the little things you may have forgotten until you can get to the store just a few minutes away. The canal was the best part of our stay! We saw jumping fish and manatees from the kitchen window! Host was extremely responsive and the Ripley Museum near by was perfect for a rain day and free on Mondays.

Luxury Family House - Near Coast - Sleeps 14
Highly recommended! Our stay was pleasant! Everything was perfect Thanks

Beautiful heated pool home, minutes from beaches
Starting from the kindness and cordiality of Carolina, she has quick attention to the guessed and the place is quiet, fast access, cozy, spacious, pleasant. you feel at home. I would definitely come back. Thank you Carolina.

Settle Down in Sarasota
I stayed at Pam's home with my 82 year old father whose mobility is not the greatest!! Pam bent over backwards to make our experience at her home more comfortable and relaxing!!! Not only a beautiful home, but excellent service from the owner!!!

Backyard Oasis, Dual Master suite, Pool home!
We had a wonderful time at Kara’s place! Kara was prompt and super helpful when we encountered a random beeping upon arrival and was soon fixed. The house was great and very comfortable but our favorite part was the lanai and pool! Everything was clean, spacious, and the pool was the perfect temperature for a daily dip! During our stay landscaping, pest control, and pool cleaners came! This showed us even more the effort they place in maintaining the home. It was a perfect way to celebrate my 40th! With just a short 15-20 min drive to the beach we went multiple times but mostly enjoyed our stay at the house, lounging in the lanai and swimming in the pool. We will definitely keep it in mind for future vacations!

Gorgeous Peaceful Cottage
Eliana was wonderful! Her place was very clean and comfortable. The space looked just like the pictures. I would recommend this place to anyone staying in the area. Great location and easy access to major roads. The location is quiet and peaceful. Eliana was very responsive and super friendly!
Condo rentals with a pool

Beach Escape & Pool, steps to Beach & restaurants
Cyndi and Colin - Thank you so much for having us! We truly enjoyed the weekend to the fullest thanks to this wonderful condo. Super close to the beach, restaurants, bars, and activities. Our favorites were Island Time (drinks), Daiquiri Deck (HH 3-7 Daily), Shore on LBK, and Drift Inn (drinks, cash only). Had an incredibly scenic dinner at Waterfront Beach House on the final night, about a 1 minute walk and you can enjoy a delicious dinner right on the beach! The condo had pretty much everything you could ever need for a beach trip, with Publix accessible nearby for anything additional we needed. Colin was so incredibly accommodating by letting us check in early and check out late. The condo was perfect size for us as a couple, and could certainly accommodate a couple small kids as well. We will absolutely be back in the area soon and will be booking with Colin and Cyndi again!

A&A's Paradise near IMG & Anna Maria beaches
We truly loved staying at this beautiful condo! It was super-super clean, modern-designed, had everything we needed, and even much more! Full spectrum of laundry/cleaning/bathroom supplies in abundance. The space is very cozy, stylish, and the location was really convenient - walking distance to Publix, good restaurants, and other useful places. Andrew and Angel are great hosts and kindest people! Responded immediately and positively to all our questions. Can’t wait to get back and stay here again! We feel lucky to find this place! Thank you Angel and Andrew!

6 min to Siesta Beach | Heated Pool | Lake View
We had a lovely stay at Doris's place! When we got there it was easy check in and a very nice/clean place. There was little to no confusion the entire stay. Overall, it was a lovely place to stay!

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 😊

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

Condo with a View 1: Beachfront!
This was our second stay here. You can’t beat the location and view! Nice and clean. Comfortable with all the amenities you need. Heidi is consistently friendly, responsive and helpful. Always checks in on us to make sure everything is going well. She had a birthday treat delivered for my husband’s birthday during our stay. Just an above and beyond hostess! We will definitely be back again.

Modern Waterfront Condo - Captivating Sunset Views
Rosana was an excellent host- very responsive, kind, and accommodating. Fun location on the bay with a great view, pool with towel service, and bar/grill with great burgers. Fire pit on the little beach at night with great view of sunset. The unit is in a quiet location within the complex with a view of the beach and bay. The trade-off is that the unit is a bit far from the elevator (though close to stairs). Great experience overall.

Near beach. Daily rentals. Pool. king bed
Great location with an easy walk to the beach. Quiet neighborhood and clean area!
Home rentals with a private pool

New! Beautiful Pool Home Near Siesta Key Beach
It was a short stay for us, but it was exactly what we needed! The house was fully stocked with necessities. Instructions were very clear, not overwhelming. The neighborhood is nice, very close to supermarkets, shopping, restaurants, coffe shops, beach, and local areas whether you want a casual night out or a party night out! Great location😉

Great 6br for All Ages/heated Pool 5 Min to Beach
Place was amazing! I would give 6 stars if I could! Check in and check out were easy and host always responded very quickly to any messages! Will definitely stay here again and recommend it to anyone else! The house is also a lot bigger in person! Thanks again guys, I loved your place!

Sunny Palmetto Oasis: 4br Home with Private Pool
Thank you RedAwning Rental for the stay in Palmetto!

Comfy Home W/ Heated Pool Near Siesta Key Beach
Quick stats about vacation rentals with a pool in Whitfield
Total rentals
110 properties
Nightly prices starting at
ﺩ.ﺇ110 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
Destinations to explore
- Tampa Bay Vacation rentals
- St Petersburg Vacation rentals
- Seminole Vacation rentals
- Tampa Vacation rentals
- Central Florida Vacation rentals
- Four Corners Vacation rentals
- Kissimmee Vacation rentals
- Orlando Vacation rentals
- Saint Johns River Vacation rentals
- Fort Lauderdale Vacation rentals
- Gold Coast Vacation rentals
- Miami Vacation rentals
- Kid-friendly rentals Whitfield
- Rentals with a fireplace Whitfield
- House rentals Whitfield
- Fitness-friendly rentals Whitfield
- Pet-friendly rentals Whitfield
- Rentals with outdoor seating Whitfield
- Family-friendly rentals Whitfield
- Waterfront rentals Whitfield
- Rentals with a washer and dryer Whitfield
- Rentals with a patio Whitfield
- Rentals with a fire pit Whitfield
- Rentals with pools Manatee County
- Rentals with pools Florida
- Rentals with pools United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Anna Maria Island
- Siesta Beach
- Dunedin Beach
- Anna Maria Public Beach
- Crescent Beach
- John's Pass
- Turtle Beach
- Caspersen Beach
- Bean Point Beach
- Busch Gardens Tampa Bay
- Raymond James Stadium
- Cortez Beach
- Lido Key Beach
- Amalie Arena
- Coquina Beach
- Gulfport Beach Recreation Area
- Vinoy Park
- North Beach
- Fort De Soto Park
- Manasota Key Beach
- Streamsong Resort
- Tampa Theatre
- Jannus Live
- Curtis Hixon Waterfront Park