
Family-friendly holiday rentals in Whitfield
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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!

Longboat Key-OCEAN FRONT- on the beach
Absolutely loved our stay! The place was spotless, beautifully decorated, and had everything we needed for a relaxing getaway. The location was perfect—just steps from the beach with stunning views and peaceful surroundings. Cindy was incredibly responsive and welcoming. We’ll definitely be back—highly recommend

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.

Florida Bella Rosa-2 spas & pools near IMG/beaches
Our family really enjoyed our stay at Daniel’s condo in Bradenton. It was very clean, updated, quiet,and spacious with great amenities in the complex. We highly recommend this rental to couples or families. Daniel also provided perfect communication and local recommendations. Very convenient area with great access to grocery and 15 minutes to beaches at Anna Maria Island.
Family- and pet-friendly home rentals

Charming Mid-Century Retreat by Arlington Park
We had an amazing stay at this adorable mid-century retreat! The decor was stylish and nostalgic, and the amenities were top-notch. The location was perfect for exploring our favorite beach spot. Our hosts were great about communicating and made sure we had everything we needed. Can't wait to come back.

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!

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.

"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.

pet friendly on an equestrian farm
As a solo 74 year old gal with an English cocker, safety is most important. I was very comfortable and felt safe. there. Just a lovely place and nice people

Las Palmas Beach Rentals unit 2
cute little beach apartment. clean and comfortable. We loved being super close to the beach. and the outdoor hose and shower was handy. nice of them to provide some beach items too like chairs, a boogie board and beach towels. AC gets very cold, which my husband was happy about. We will definitely be back to Ana Maria Island! its an amazing beach.
Family-friendly home rentals with a pool

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.

5 minutes to private Siesta Key Beach + 2 pools
Solen was an amazing host—very responsive, friendly, and helpful throughout our stay. She even brought us a brand-new can opener when we needed one! The house was spotless, cozy, and located in a great area. We had a wonderful time and would definitely stay again!

Discount 33% June 3-Day and July 4-Day w/Dock-Pool
My family and I absolutely loved our experience!! The hosts were attentive and quick to respond with clear instructions. House was cleaned and amply stocked with everything you need for a family of five. The pool was amazing and we definitely saved some money by having a fully functioning kitchen and grill for dinner and lunch. Very close to the beach. Two scoops ice cream is amazing with quick service as it is very busy and the general store was only a quick drive to get anything else we needed or forgot to pack. Bean Point beach is where you want to be if you don’t like overcrowded beaches, however, parking is limited so I recommend getting there early!! Also recommend renting a golf cart for extended stays and if you have kids like I did. Plenty of options around the island. I would recommend 100% and we definitely will be back!!

Sparkling Clean Pool Home near Gulf Beaches
We spent a relaxing weekend at this lovely Airbnb and couldn’t be happier with the experience. The place was exactly as described—clean, cozy, and thoughtfully decorated. The host was friendly and responsive, providing clear instructions for check-in and great recommendations for nearby restaurants and activities. We especially enjoyed the peaceful backyard patio—it was the perfect spot for morning coffee and evening wine. The location was ideal—quiet and private, but still just a short drive to everything we wanted to see and do. It made a great home base for our weekend adventures. We’d definitely stay here again. Highly recommend it for anyone looking for a stress-free and enjoyable escape!

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!

Relaxing Condo Retreat Minutes from Siesta Key
Place is perfect for a family. David and Betsy provided all the things we needed for our little ones (pack and plays, baby gates, baby beach tent, etc.) Communication from host was also quick. Loved having access to a pool too. Less than 10 minutes from the beach. Would likely stay here again if we came back to Sarasota!

Drift Inn B Heated Pool & Private Beach Access!
We really enjoyed the Drift Inn Unit B! Our family of 4 felt right at home and comfortable, with enough room for all of us. The condo looked like the pictures and had all the listed amenities. We utilized the washer and dryer, and the included beach gear was a great plus! The shared pool was very nice and clean, and the location of the house was just perfect! It felt safe and secure and was quiet and private, even though it was on the main drag of the little community. It was awesome having the beautiful beach a 3-minute walk in one direction; and little shops, stores, restaurants, and bars just a few minutes walk in the opposite direction. We did not have to contact the host during our stay, but he sent very clear and helpful check-in/check-out instructions with plenty of time before our check-in. There was even a little book at the condo with additional information. I can’t say enough good things about we really enjoyed our time here and we hope to come back!
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
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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