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
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Popular amenities for Whitfield rentals with a pool
House rentals with a pool
Home in Sarasota
4.63 out of 5 average rating, 19 reviewsVitamin Sea: Private Pool, Downtown, and Beaches!
My family and I stayed here for 10 days and we can say it was one of the best stays. Our flight landed early and we reached out to the host to ask for an early check in, they responded back fast and were able to accommodate us. Once inside the house everything was clean and the kids went right into the pool which was also very clean. Overall we felt right at home and the whole stay was 10/10!
Home in North Port
5 out of 5 average rating, 12 reviews3bd 2th Solar Heat Pool Large home W/ big yard
Great Place to stay. If ever in the area would stay again.
Home in Seminole
4.92 out of 5 average rating, 107 reviews4 bedroom and private pool, near to Clearwater
due to Helene there was no wifi. Maria and her husband purchased a separate wifi device just so we had wifi. very responsive and helpful.
Home in Bradenton
4.87 out of 5 average rating, 289 reviewsLarge 4 bedroom pool home tiki bar close to Ami
Great stay. This place is near to beaches in Sarasota. Host is very responsive .
Home in Siesta Key
5 out of 5 average rating, 27 reviewsBeautiful House with Heated pool
Our girls trip weekend was a huge success!! We all had a wonderful stay here and we didn’t have a single complaint. Check in was super easy and went off without a hitch. The house is exactly as pictured, very open and comfortable. We did not have a single issue while staying! Highly recommend staying here, I promise we will be back!
Home in St. Petersburg
4.98 out of 5 average rating, 176 reviewsSurf’s UP! Pool, Cabana & Poolside bungalow!
~~STOP LOOKING THIS IS THE PLACE!! ~~ We came to Florida to enjoy the surroundings but ended up staying at our AirB&B the whole time because it was so PERFECT! Grocery and dining across the street, extremely comfortable beds, lounges and couches all over the property. We were in HEAVEN. Kitchen has everything you could need, and there were so many beautiful touches. This will be our first choice to stay every time we return to this area. You will not be disappointed!!
Home in Seminole
5 out of 5 average rating, 23 reviewsAffordable luxe pool home near beaches
Sue and Joe are amazing host. The pictures of the home are beautiful but its even better in person. Both Joe and Sue were very quick to respond to any questions that I had. The home had everything you could need for your vacation. My Family and I will definitely be back to their Airbnb in the future.
Home in Largo
4.95 out of 5 average rating, 133 reviewsBeautiful Heated Pool house, 10 mins to the beach!
Thanks for the wonderful hospitality! Anna was very responsive. We had a pleasant stay. Good location and lots of restaurants and things to do close by.
Condo rentals with a pool
Condo in Bradenton
5 out of 5 average rating, 5 reviewsLovely Condo, Heated Pools, AMI, IMG, Top beaches
This condo was nice for a central location. We went to downtown Bradenton to the Bishop Museum, to Anna Maria Island and to Palmetto. The kitchen had all the basics and the freezer has an ice machine which was nice. We utilized the beach towels only but they also provide beach chairs and some pool noodles. There was some siren noise from the main streets near by, but nothing awful. Lots of closet space, great to have a washer and dryer and the guest bath has been nicely redone. We would stay here again.
Condo in Osprey
4.89 out of 5 average rating, 9 reviewsLovely 2 bedroom condo with pool & tennis courts
This is our second year staying in this complex. There are many walking trails that are a short drive, close to several beaches, restaurants and grocery stores.
Condo in Saint Pete Beach
4.88 out of 5 average rating, 146 reviewsSun, Beach Views, and Smiles!!!
We hated to leave! It was perfect for our stay. Very clean and steps away from the beach, close to everything store wise/ restaurants.
Condo in St. Petersburg
4.91 out of 5 average rating, 22 reviewsLovely 2 bedrooms condo with pool in Boca Ciega
We had a great stay! The views were gorgeous from our balcony each evening and our host Matt was extremely responsive. He had great recommendations on pet-friendly beaches. Location was perfect to get between beaches and downtown St. Pete. We highly recommend this place, host and stay!
Condo in Siesta Key
4.87 out of 5 average rating, 101 reviewsSiesta Village Short Walk to Beach w heated Pool
This place was fantastic with everything we needed. It was close to everything and a short drive to some of the other local activities. Short walk to multiple beach entrances and a cart, chairs, umbrella, etc. was all available to take to the beach. There’s a local shuttle that takes you all over the island for free and a market around the corner that’s fully stocked with everything you need to cook some meals there. We did the night time LED kayaking and then did the Mangrove Eco Tour with Kayaking SRQ, ask for Kaleb for the mangrove tour, the man knew everything about the area, its history, conservation, and gave some great restaurant and attraction recommendations in the area. Or… just hang out at the beach. We were there during tropical storm Debby and Kathryne communicated with us throughout. Absolute amazing stay… even with a tropical storm! We can’t wait to come back.
Condo in Bradenton
4.87 out of 5 average rating, 71 reviewsLakeside Condo. Beaches, Restaurants, IMG nearby.
This was a great stay !! The location very convenient ! Very nice and place ! Has 2 bathrooms ! Access to the back yard with a nice pond view ! It has balls and games for the family to use ! And chairs to take to the beach ! Will be back ! Totally recommend !
Condo in Seminole
4.97 out of 5 average rating, 143 reviewsSUNNY DELIGHT! HEATED POOL 2 miles to the beach🐶
Sandra’s place is lovely! Extremely clean, comfortable, and well stocked kitchen and toiletries. She really has thought of everything. It was helpful having ziploc bags and containers for packing food on the go, spices and pantry essentials, first aid kit for a bandaid that was needed, fans for the bedrooms, etc. I stayed here for a girls weekend and the three of us would all highly recommend it!
Condo in Sarasota
4.97 out of 5 average rating, 61 reviewsPeaceful retreat, pool, hot tub, near Siesta Key!
Great place to stay! It was a very safe community with nice extras and was pretty close to the beaches. So nice to have the extra beach supplies to go shark tooth hunting at Caspersen Beach. The condo was clean and spacious.
Quick stats about vacation rentals with a pool in Whitfield
Total rentals
100 properties
Nightly prices starting at
$30 before taxes and fees
Total number of reviews
3.5K reviews
Family-friendly rentals
60 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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