Family-friendly vacation rentals in Siesta Key

Find and book unique family-friendly homes on Airbnb

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Top guest favorite
Home in Bradenton
4.98 out of 5 average rating, 173 reviews

Sunshine Retreat with heated saltwater pool

SallyannRating, 5 stars3 months ago
Christmas at Chris’ was a lovely stay! The pool area was amazing and the pool lovely and warm, we spent almost everyday out there even in December. We made great use of the 4 sun loungers. The house is situated in a quiet area, with plenty of space for several cars on the driveway. With great access to Manatee avenue and not far from Holmes Beach. Don’t forget to stop in at Wawas only a short walk away for one of their coffees, it competes with Starbucks in my opinion lol. The house was stocked with all the essential amenities, including towels (beach ones too), washing up liquid, washing powder, dishwasher tablets, water in the fridge, body wash and shampoo. The house comfortably hosted my party of 5, 2 children, an 84 year old grandmother, myself and my husband. A great family vacation rental, hope to be back soon!

Popular amenities for Siesta Key family-friendly rentals

Family-friendly home rentals with a pool

Top guest favorite
Home in Sarasota
4.98 out of 5 average rating, 133 reviews

Gorgeous Home / Heated Pool and Spa

DawidRating, 5 stars1 week ago
A great house for two families with kids! Very clean and spacious. The heated hot tub and pool was amazing! The host was very friendly and responsive. The drive to Siesta Key beach was short ever with traffic. We would definitely come back!
Guest favorite
Home in Bradenton
4.95 out of 5 average rating, 246 reviews

Paradise Cove

SusanaRating, 5 stars2 months ago
This place was perfect! Beautiful and peaceful backyard with a pool, we didn’t get to enjoy it but overall this place was beautiful.
Guest favorite
Home in Holmes Beach
4.97 out of 5 average rating, 130 reviews

Twin Palms: Big House Steps to Beach w/Lush Pool

ElisabethRating, 5 stars2 weeks ago
Stay was wonderful. house was perfect, hosts were incredibly thoughtful and responsive. My family of 8 travels together so the two bathrooms was a little tight. Would have loved an extra bathroom or two for the price but the heated pool more than made up for it. The heated pool kept my grandson entertained and enthralled all week as did the toys made available to him. in addition, the childproof amenities were amazing and made the trip easy and relaxing. Kuddos to the hosts
Superhost
Home in Port Charlotte
4.84 out of 5 average rating, 156 reviews

Waterfront Pool and Dock! Great Family Retreat

IsaacRating, 5 stars15 months ago
Beautiful spot, not far from numerous restaurants and things to do. Not far from the Charlotte Event Center. Good amenities, stocked cupboards (coffee filters, seasonings, etc). Definitely would stay here again if we visit.
Guest favorite
Home in Bradenton
4.9 out of 5 average rating, 99 reviews

Large Sparkling Clean Pool Home West Bradenton

MargotRating, 5 stars1 month ago
The house was perfect and just as described. Terrie and her husband were so helpful with me having a late arrival. Directions on what to do when leaving were very clear. Yard was great for being fenced in for my service dog and the area was perfect for walking. Grocery store very close as well as some specialty coffee shops. Lots of separate spaces to relax in which was great.
Guest favorite
Home in Sarasota
4.95 out of 5 average rating, 206 reviews

2bed/2bath with POOL house, close by SIESTA KEY!!!

JoelRating, 5 stars1 week ago
Romualda’s home was very clean, beautiful, and modern. She was very communicated from the time we booked the AirBnb, to the time we checked in, and the time we checked out. We felt right at home as she had many ameneties that were offered and more. We will definately book again next time we are in town.
Guest favorite
Home in Bradenton
4.76 out of 5 average rating, 245 reviews

Tropical Paradise - Private Pool - Close Beaches

PatriciaRating, 5 stars2 weeks ago
Karin is a wonderful host and responds quickly to any questions. She is conscientious and was sure to keep us informed when the dishwasher needed to be replaced. The house is clean and comfortable, the pool and patio area is spectacular. We would stay here again. The location was perfect for our stay in Bradenton.
Guest favorite
Bungalow in Sarasota
4.82 out of 5 average rating, 151 reviews

Pink Flamingo: 4 Beds/3 Baths Screened Pool Oasis

MiriamRating, 5 stars3 months ago
We enjoyed our stay at the Pink Flamingo house. The house was well supplied, and clean. I would definitely recommend this house for any one that has a bigger family to accommodate for. The children enjoyed the heated swimming pool. Yvonne was very easy to work with and always responded when we had questions.

Family-friendly home rentals with air conditioning

Guest favorite
Home in Anna Maria
4.84 out of 5 average rating, 32 reviews

A Wave From It All - PETS! Oasis Near Gulf Beaches

RobertRating, 5 stars6 months ago
Thanks again for hosting my family and I. It was the perfect staycation for us. The backyard is the best part of the house. It was a great set up to hang in the pool and be able to watch the football games.
Superhost
Bungalow in Bradenton
4.69 out of 5 average rating, 35 reviews

3/2 Home Heated Pool/close to Anna M. Beaches/ IMG

JoAnneRating, 5 stars14 months ago
Great place and excellent host. Loved the pool and watching the egrets by the lake. Thank you Tomas!
Superhost
Villa in Sarasota
4.75 out of 5 average rating, 124 reviews

Aloha Villa Pet Friendly 3 miles to Siesta Key #2

GrantRating, 5 stars11 months ago
Great clean place to stay at and they were very fair on price
Guest favorite
Home in Indian Beach-Sapphire Shores
4.93 out of 5 average rating, 68 reviews

The Happy House - Seeing is Believing!

AmberRating, 5 stars1 week ago
Very nice home. Cozy space and beds. Nice pool. Our electric went out for about 12 hours so we couldn’t see anything the last night, but they were very attentive. It wasn’t their fault at all. Other than that, wonderful stay.
Top guest favorite
Home in Sarasota
5 out of 5 average rating, 30 reviews

Family friendly with large pool

JacklynRating, 5 stars7 months ago
I had a large party of 4 adults and 6 children and there was plenty of space for everyone. The house itself was stunning. We all enjoyed the pool and hot tub. Definitely would recommend others to stay here.
Guest favorite
Home in Sarasota
4.98 out of 5 average rating, 63 reviews

FAMILY-FRIENDLY HOME CLOSE TO EVERYTHING

SalRating, 5 stars1 month ago
Niconle was a wonderful host. She communicated frequently and made us feel at home. The location is peaceful. The lanai faces a pond with frequent visits by many different shore birds. The kitchen is well equipped. We would stay at this location again.
Guest favorite
Home in Bradenton Beach
4.77 out of 5 average rating, 43 reviews

AMI Sunset Beach - Pool Side Retreat w/ Pool +Deck

AshtonRating, 5 stars2 months ago
Very nice place. Very clean, and sticked with everything you need. With an amazing rooftop view of the ocean. Pool was heated. Loved this area and the beach was only literally across the street. We are from this area. And we enjoyed our stay very much Rex was a wonderful host.
Superhost
Apartment in Sarasota
4.86 out of 5 average rating, 29 reviews

LUX VILLAs close to sparkling Siesta Beach.

MarciaRating, 5 stars5 months ago
My two boys and I truly enjoyed the condo. It was clean, tidy, roomy, well-equipped, and conveniently located. The community was quiet and peaceful. My boys loved the pool and I loved the hot tub. We were extremely pleased. While we were given a unit that differed from our original request, we understood the reason given and we were in no way disappointed with the new arrangement. The unit was perfect for us and we would definitely return. Bea and her assistant were quick to respond to my questions prior to arrival. We had no issues during our stay, so we never needed to communicate while we were there. Check-in and check-out were both extremely easy.

Family-friendly home rentals with a hot tub

Guest favorite
Home in Bradenton
4.93 out of 5 average rating, 68 reviews

Heated Pool_Hot Tub/Spa_Close To Beaches_Remodeled

ValerieRating, 5 stars5 days ago
Casey was a friendly and responsive host! The house was the perfect space for our family and friends to stay together but have our own privacy! Any help or concern we had, Casey jumped right on it to solve our problems.
Superhost
Condo in St. Pete Beach
4.88 out of 5 average rating, 146 reviews

Sun, Beach Views, and Smiles!!!

KendraRating, 5 stars3 months ago
We hated to leave! It was perfect for our stay. Very clean and steps away from the beach, close to everything store wise/ restaurants.
Guest favorite
Apartment in Pass-a-Grille Beach
4.94 out of 5 average rating, 103 reviews

Traders' Haven - Historic 8th Ave Mega Beach Condo

ColleenRating, 5 stars6 months ago
Our group had such a great stay. The location was great and it was the perfect spot for a beach weekend. Daniel was super helpful and responsive to any messages sent during our stay. We loved the spacious quirky layout of the apartment and would definitely stay here again!
Guest favorite
Condo in Bradenton
4.84 out of 5 average rating, 126 reviews

Shorewalk upgraded condo upstairs unit 4415

BrianRating, 5 stars2 months ago
Enjoyed our stay. Very quiet location and convenient to everything
Superhost
Home in Sarasota
4.76 out of 5 average rating, 111 reviews

5min to Siesta, Heated Pool & Jacuzzi, Grill, WiFi

BarbaraRating, 5 stars3 weeks ago
House was great, we really enjoyed our stay and would definitely book again if available whenever we’re in the area. The host was super responsive and helpful when needed.
Guest favorite
Home in Anna Maria
4.98 out of 5 average rating, 64 reviews

4 Bed 4.5 Bath Family Friendly, 3 Blocks to Gulf

NicoleRating, 5 stars3 months ago
Stayed here with the whole crew and it was perfect. Flow of the house is great for extended family and guests. Patrick is super responsive and helpful. I couldn't find something and he literally brought it over. Would totally stay here again.
Superhost
Condo in Bradenton
4.86 out of 5 average rating, 110 reviews

Florida Bella Rosa-2 spas & pools near IMG/beaches

LeahRating, 5 stars2 months ago
We are already looking to see when we can come back to Florida and stay in Daniel's rental again! It has everything you need, it is well-kept, and it is close to everything you want/need (the beach, Detwiler's, Publix, stores, restaurants). It is in a safe location. The Shorewalk ammenities (pools and hot tubs) are nice as well. Even though one pool's heater was broken, there was another pool to choose from and two hot tubs. He checked-in with us to make sure check-in went well and to make sure that our stay was going well. Daniel provided thorough instructions and recommendations for everything you could possibly need. He was a great host with a great home away from home!
Guest favorite
Home in Port Charlotte
5 out of 5 average rating, 82 reviews

Myakka River Retreat In Port Charlotte

ShelleyRating, 5 stars2 weeks ago
We had a wonderful stay at Paul and Nanci’s place! The space was clean, comfortable, and beautifully decorated, making it feel like a home away from home. Paul and Nanci were excellent host, providing clear instructions and thoughtful touches throughout our stay. The highlight was definitely the breathtaking view from the observation deck – it was absolutely stunning, especially at sunset! And as for the fishing, the fish definitely bite – we had a great time casting a line and even caught a few! The location was perfect, with easy access to local attractions and restaurants. I highly recommend staying here and would definitely return on my next trip! Thank you, Paul and Nanci, for such a great experience!

Quick stats about vacation rentals that are family-friendly in Siesta Key

  • Total rentals

    1.5K properties

  • Nightly prices starting at

    ﺩ.ﺇ220 before taxes and fees

  • Total number of reviews

    21K reviews

  • Pet-friendly rentals

    260 properties allow pets

  • Rentals with a pool

    1.2K properties have a pool

  • Rentals with dedicated workspaces

    620 properties have a dedicated workspace

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