
Family-friendly holiday rentals in Whitfield
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Whitfield
Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.
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Popular amenities for Whitfield family-friendly rentals
Family-friendly home rentals with a hot tub

Gorgeous Home / Heated Pool and Spa
Just returned from another great stay at Kayla’s place. Everything was fantastic, the backyard pool and jacuzzi were amazing. We also really appreciate Kayla’s responsiveness. Looking forward to returning next year!

Spacious Home Solar-Heated Pool and Spa
Great value!! We loved the pool area and very quiet neighborhood!

Now NEW AUG Openings! Sarasota #1 Lux BEACH Villa
We had a fantastic stay! The beach was just a short walk away and so easy to access, which made our days relaxing and stress-free. The private pool was a huge hit—our kids were entertained for hours, and it gave us plenty of time to unwind. Christopher was incredibly friendly and went above and beyond to make sure we had everything we needed. You can tell he truly cares about his guests’ experience. We would absolutely stay here again!

PRICELESS VIEW Boca Ciega Bay Condo 1/1 #209
Just like the photos! Beautiful and comfortable for our stay… Love the location, close to everywhere we wanted to go! Comfortable bed, the couch could use some updating. The pool is very warm, but a nice spot to hang out. Didn’t get to see any dolphins 😞 Overall, enjoyed our stay, will definitely be back!

The Oasis
Russell’s place was just as described. The bay of the bay was beautiful! This condo was within short driving distances of many great local beaches and restaurants. It had all the amenities, linens, and other items needed to make our stay perfect. Russell checked in with us prior to our stay, during and after.

Waterfront condo on top floor @ Boca Ciega Resort
good place. easy free parking. elevator .check. pool and hot tub very nice. only negative was how close it was to noisy road. otherwise, no complaints.

The Guest House at Riverbend Retreat Fla.
She was an amazing host, and the place was super nice and peaceful

Private Pool, Jacuzzi, Walk to Beach.
Robert was a great host! Lots of great local recommendations. His place was extremely clean and had everything you could need. Well stocked with essentials. Close to Indian Shores Beach and Clearwater Beach. Had chairs, umbrella and cooler to use at the beach, great amenity!! You won’t be disappointed!! Highly recommend to stay at Roberts place and we plan to be back soon!!
Family- and pet-friendly home rentals

Open Water Home Bring your boat! No storm issues.
Beautiful home with an amazing view. My boyfriend had a blast fishing all weekend. We caught some catfish and even saw dolphins swimming. 10/10!

The Pineapple Suite.Teal tropical home in Sarasota
We really enjoyed our stay and Tim was a great host. Highly recommend this property! It’s super cute and comfortable. I would stay here again.

Sarasota Pool House
This was our second time staying at Lubos pool house. We really enjoyed our stay and are already looking far time to escape back. Great location near restaurants, stores and beaches. Back yard and pool are a dream and very peaceful.

Historic Home with Boat parking 0.6M of Boat Ramp
We were in town for a family members wedding. This house was a relaxing calm home for the hectic fun wedding wkend. Loved the coastal FL decor and vibes. Definitely felt like I was home. Very spacious for my husband and I and our 2 teenagers. Location was great! Close to all our family and friends in Palmetto and Bradenton, as well as the ceremony hall in Bradenton and just minutes away from the reception hall in Palmetto. Great communication with the hosts. Would definitely recommend and look them up when were are back down.

Sarasota Sandpiper: 4 Bed/3 bath + Pool
We had 3 adult dads and 3 teenage sons stay for 5 nights to compete at the US Rowing Youth Nationals at Nathan Benderson Park and the house was perfect. Yvonne was very attentive to our last minute booking. Bedrooms were perfect for the amount of people, kitchen was well stocked to handle 6 people plus more. We grilled out one night and the propane grill was perfect. We hit the pool once and was the perfect size. Bathrooms were very clean and neighborhood was quiet at night. House was in close proximity to the park as well as other restaurants so worked out for the back and forth daily driving that we did. Highly recommend Yvonne’s home for future groups/families

Duplex - just mins to Siesta Beach - Pet Friendly
We had an absolutely wonderful stay at Sheila's place! The location was perfect, close to everything. Sheila was incredibly responsive and helpful throughout our stay, answering all our questions promptly. We highly recommend staying here!

"Chill Time” Great Location in Sarasota
Perfect place for our stay. The location is very quiet and peaceful. There are parks and shops within walking distance or a quick drive away. The house was very clean and had everything we needed for a comfortable stay, for cooking and for grilling. The host was very nice and responsive and made us feel welcome and comfortable. Thank you for being a great host!

The Cottage, very close to Siesta Beach!
Fair price. Great Location. Awesome / quick communication.
Family-friendly home rentals with a pool

Crows Nest at Spinnakers Vacation Cottages
We stayed for one week and were very pleased with our visit. The house, grounds, and pool were very clean. The house had everything we needed, was super close to the beach, and we had the pool to ourselves most of the time. We loved our stay at Spinnaker's Cottage and had a very relaxing and enjoyable time. We would definitely stay here again!

Twin Palms: Big House Steps to Beach w/Lush Pool
Staying a this Airbnb on Anna Maria island was nothing short of amazing. From the moment we arrived, everything exceeded our expectations. The location was unbeatable, just a short stroll to the beach, where we spent our mornings. The home itself was spotless, beautifully maintained, and had everything we needed. The private pol was a dream-crystal clear and perfect for relaxing after a day at the beach. It truly felt like our own personal oasis. What really made the experience stand out was the host. Communication was prompt, friendly, and thoughtful from start to finish. They went above and beyond to make sure we felt welcome and had everything we needed to enjoy our stay. If you're looking for a peaceful, beachside retreat with all the comforts at home- and then some- this is the place. Anytime we travel to this island this is the first place I will check to see if it is available.

Near Downtown/Beach | Tropical Villas Venice Beach
Honestly, one of our best trips. The location, price, amenities, ease. Couldn't have asked for a better place. Martin and his staff were amazing. Even had a lavender candle gift left for our anniversary. Would love to go back. Between my wife and I, I can say this was one of our best Florida vacations.

Hansen- Gorgeous 3BR/2BA Villa near Siesta Key
Great home, close to the beach and had a ton of fun.

TropicalPOOL Oasis- 5 Minutes to Beach-Fun Decor!
My stay at Stephanie's property was very pleasant. I never had to call her. Everything at her property is excellent. The house is spectacular, the pool was GREAT!!!, and the fire pit was the best. I have no hesitation in recommending her property. Thank you, Stephanie!

SIESTA BEACH HOUSE HEATED POOL☀️🌴3 MIN TO BEACH!!
Great place, very clean and had everything we needed. Instructions very clear and the pie waiting for us in the fridge was much appreciated! The beach gear was a nice touch, just a pity the weather wasn’t kind to us.

Relaxing Condo Retreat Minutes from Siesta Key
I enjoyed my stay. David is very responsive and gives detailed instructions on how to get into the house. The area is convenient, the neighborhood is peaceful, and the unit is clean. I recommend booking this place!

The Key to a Great Vacation!
The place was great! Very well stocked kitchen, bathroom and even had beach stuff available for use. Location was perfect, a short walk to the beach and close to restaurants.
Quick stats about holiday rentals that are family-friendly in Whitfield
Total rentals
90 properties
Nightly prices starting at
$83 NZD before taxes and fees
Total number of reviews
3.2K reviews
Pet-friendly rentals
40 properties allow pets
Rentals with a pool
70 properties have a pool
Rentals with dedicated workspaces
60 properties have a dedicated workspace
Destinations to explore
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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