
Family-friendly holiday rentals in The Meadows
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Top-rated family-friendly rentals in The Meadows
Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.
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Popular amenities for The Meadows 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!

Siesta Key Serenity At The Palm Bay Club
Super clean, quiet, comfy bed. We enjoyed the bayside pool. Nice views. Palm Bay club nice benefit as after a short walk over to the beach we enjoyed the chaises delivered and set up close to the water and hole drilled for our beach umbrella. Amazing sand is not over rated. Warm gulf waters and easy entry and exit. Breeze Trolley with their app made getting around without driving convenient . Lots of fun food and shops minutes away. This bayside spot a was a delight.

Estate Living in The Meadows Golf Community
This was our second stay in this stunning home. Jennifer and Amy were excellent to work with. They respond to communication promptly and authentically cared that we had the perfect stay. The home is beautiful and had everything we needed. My husband and I are already talking about returning. Highly recommend!!!

Private View Villa/Heated Pool/Pickleball/7883
Spacious home with all the amenities you need, well equipped kitchen. We loved the lanai and had all our meals outside. Green and silent surrounding, nice neighbors. A lot of beautiful beaches within 45min (AMI) or just 15min (Siesta). Good shopping possibilities. We had a great time and will be back!

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

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!

5min to Siesta, Heated Pool & Jacuzzi, Grill, WiFi
We loved the pool and hot tub. Ben was very responsive when I asked about if there was a speaker we could use and he dropped one off at the front door within minutes. Great location and price was reasonable. We would Definately stay again!

Siesta Key Cottages Crescent 1B Beach/Pool/Hot Tub
We had a fantastic stay at this home! Our family of five (2 adults and 3 kids) absolutely loved it. The house was clean, well-maintained, and located in a perfect spot—just a five-minute walk to the beach. It had everything we could possibly need, from kitchen essentials to beach toys for the kids. What really made the stay special was Dave’s hospitality. He was incredibly responsive and provided excellent recommendations for local beaches, restaurants, and more. His tips really helped us make the most of our trip. We highly recommend this place and will definitely be back!
Family- and pet-friendly home rentals

Paradise Retreat
Maggie’s place is perfect!! So convenient to everything you need!! Everything in house that you would need and also everything you need to go to the beach!!! Maggie is very fast to responding to any questions you have!! 5 star for sure!!

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!

Aloha Villa Pet Friendly 3 miles to Siesta Key #2
I visited Sarasota with my family from the state of Rhode Island from April 4 to April 7 and we stayed at Jason’s & Laura house and it was an amazing experience. The house was very clean and organized. The house is located on a great neighborhood, super safe and great amenities. The house was stocked with beach supplies like beach chairs, beach towels, a boogie board and a beach cooler that was so nice. The house was exactly what we were expecting, I would recommended to everyone. Thank you Josh and laura.

Tropical Paradise - Private Pool - Close Beaches
Will definitely stay again if I ever come back this way. I wanted a place that had a private pool and was pet friendly. I got both. The neighborhood is peaceful. The house is very spacious and clean. One downside, there is no tv in the master bedroom but that was fine too. Don’t need to be in bed with a pool like this one. Thank you for allowing me to stay.

5 Star! Walk/Bike DTN ~ 5 mi to Lido Beach Pets Ok
We had a wonderful time in Sarasota. Maureen and Patrick are clearly hosting pros. The kitchen was well-stocked, so we cooked most of our meals, made coffee/tea in the mornings, and kept groceries from the nearby Publix in the fridge. We enjoyed making dinner and sitting out on the screened in porch. The neighborhood was very residential and safe. The bathrooms and bedrooms were well-stocked and comfortable. Five college girls slept comfortably across the three rooms and I would say one more could definitely have fit as well. The house had a carport with a washer and dryer with detergent, beach chairs, umbrellas, and puzzles. Even when it rained, we enjoyed sitting in the house and reading because the space was relaxing and comfortable If you’re planning on going to the beach, download the Bayrunner/Breeze Rider apps to catch the free trolley. The trolley was a short walk away through the neighborhood and we enjoyed riding to the beach every morning.

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.

Home away from home mins to Siesta Beach!
Excellent host! Would stay again! Great location and great home!!
Family-friendly home rentals with a pool

Best Siesta Key Condo
We had a very good time at Siesta Key and enjoyed our time at Maureen's place. The building is older, the amenities are well maintained and the condo itself is well cared for. I did find some mystery stains on the mattress and the decorative pillows in my room, but I'm guessing they are just spills that were difficult to get out. More importantly, the boat dock is usable, albeit with some difficulty if the boat is larger than 22 feet or so. We figured out on the second day that the best way to dock was parallel to the intracoastal between the posts and to tie off with lines on either side of the stern and with a single line on the bow. I would check ahead to make sure the dock is available, but we had no other boats docked there on a holiday weekend. The private beach access was a lifesaver on a holiday weekend, despite the short walk required to get there. Having both intracoastal and beach access is the biggest value of the place in my opinion.

Super Clean! 2/2 condo Walk to SKey!
This place was perfect for two couples and close to the beach etc The beds were comfortable and check in and check out easy. We would stay here again

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!

Cozy, Remodeled Studio Steps from Siesta Key Beach
Perfect spot right across from Sarasota Beach! Quiet, very clean, great pool, and very responsive host! We loved our stay and have favorited Vanessa as a host so we can check out her properties when we come back. Highly recommend this host and property for your trip to Siesta Key.

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

The Sea is Calling
This house was beautiful and we felt right at home! The pool was wonderful!! They provided everything you need for a beach/ pool vacation. We loved it, would stay again if in the area!!

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.
Quick stats about holiday rentals that are family-friendly in The Meadows
Total rentals
30 properties
Nightly prices starting at
$116 NZD before taxes and fees
Total number of reviews
160 reviews
Pet-friendly rentals
10 properties allow pets
Rentals with a pool
30 properties have a pool
Rentals with dedicated workspaces
20 properties have a dedicated workspace
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- Anna Maria Island
- Siesta Beach
- Anna Maria Public 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
- Curtis Hixon Waterfront Park