Family-friendly holiday rentals in Siesta Key

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Siesta Key family-friendly rentals

Family-friendly home rentals with a hot tub

Top guest favourite
Home in Sarasota
4.98 out of 5 average rating, 135 reviews

Gorgeous Home / Heated Pool and Spa

CristianRating, 5 stars4 days ago
Kayla’s listing exceeded all my expectations. From the moment I booked, communication was seamless and welcoming. The space itself is beautifully decorated, spotless, and thoughtfully equipped with everything you might need for a comfortable stay. The highlight was definitely the pool — it’s great! Perfectly maintained and a fantastic spot to relax and unwind. The heated jacuzzi is also awesome — it’s perfectly functional, warm, and incredibly relaxing, making it a true standout feature of the property. The location is superb — just a few minutes’ drive to the most amazing beach in the USA! It’s the perfect base for exploring and enjoying the beautiful surroundings. Kayla was a wonderful host—friendly, attentive, and genuinely eager to ensure we had a great experience. She provided helpful local tips and made us feel right at home. I highly recommend Kayla’s listing to anyone looking for a cozy, convenient, and memorable stay with fantastic amenities. I can't wait to return!
Superhost
Apartment in St. Pete Beach
4.88 out of 5 average rating, 147 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 favourite
Flat in Pass-a-Grille Beach
4.94 out of 5 average rating, 104 reviews

Traders' Haven - Historic 8th Ave Mega Beach Condo

JohnRating, 5 stars1 week ago
We all had an amazing time staying at Transfer's Haven. The AirBnB was super easy to locate, get inside, and matched the description. The space itself was super clean and accommodating, and the area was perfect. I would absolutely stay again.
Guest favourite
Apartment
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, 112 reviews

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

TiffanyRating, 5 stars2 weeks ago
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!
Top guest favourite
Apartment in St. Petersburg
4.98 out of 5 average rating, 262 reviews

PRICELESS VIEW Boca Ciega Bay Condo 1/1 #209

MarieRating, 5 stars1 week ago
Valeries place was AMAZING! Words and pictures don't do the view from the balcony justice. The condo was cozy and very clean. It had everything I needed for a five week stay. I enjoyed coffee every morning on the balcony, watching dolphins and boats go by. The sunsets were spectacular, a perfect view from the balcony. I had an excellent experience renting from Valerie. It was exactly as depicted. I would highly recommend staying at Boca Ciega Resort in Valerie's condo. You will not be disappointed!
Guest favourite
Apartment in Bradenton
4.86 out of 5 average rating, 112 reviews

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

LeahRating, 5 stars3 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 favourite
Home in Treasure Island
4.83 out of 5 average rating, 161 reviews

Eiko Beach House 4BR/3BA Heatd Pool*Hot Tub* Pets

HeatherRating, 5 stars1 week ago
Literally the perfect house in Treasure Island. Beautiful beach, the house had everything we needed and John’s pass was walkable. We flew in, Ubered to the house and walked everywhere. Went out for dinner every night, walking to John’s Pass. You can walk everywhere from this house. Used Instacart to get delivery from Costco, Aldi, and Publix. Everything was super perfect and we barely had to pack a thing because the house is so well stocked. Cannot wait to come back!

Family- and pet-friendly home rentals

Superhost
Bungalow in Gulfport
4.9 out of 5 average rating, 133 reviews

Shady Paradise Close to All!

PatriciaRating, 5 stars18 months ago
We stayed a month and it felt like being at a real home; the house was very well equipped and full of character. On a daily basis, we had everything we needed, and the very few times we needed assistance/solving, Edie was very diligent to make sure we were happy. Extra points to the shaded parking space and the firmness of the mattress. We truly enjoyed our stay, as well as the location, the private fenced patio for our kitty, and our little casual encounters with Matt in the shared backyard/laundry area :)
Top guest favourite
Home in Bradenton
4.95 out of 5 average rating, 246 reviews

Paradise Cove

SydneyRating, 5 stars3 months ago
Clean and neat, friendly and when we wanted to extend was quick and easy to enjoy our stay longer. Thank you again
Superhost
Villa in Sarasota
4.75 out of 5 average rating, 126 reviews

Aloha Villa Pet Friendly 3 miles to Siesta Key #2

AwildaRating, 5 stars2 weeks ago
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.
Guest favourite
Bungalow in Rosemary District
4.88 out of 5 average rating, 127 reviews

2BR, 2BA home in the heart of downtown Sarasota

MattRating, 5 stars1 week ago
Such a lovely stay! Very homey and well decorated without feeling cluttered. Loads of room to spread out and terrific natural light. The beds were extremely comfortable. We were delighted by how walkable the neighborhood was and the street is super charming and quiet.
Guest favourite
Home in Sarasota
4.95 out of 5 average rating, 206 reviews

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

JoelRating, 5 stars1 month 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 favourite
Guest house in St. Petersburg
4.85 out of 5 average rating, 476 reviews

Cute home in historic neighborhood

MeganRating, 5 stars6 days ago
Fantastic and highly walkable location! A great place to stay!
Top guest favourite
Home in Siesta Key
4.91 out of 5 average rating, 117 reviews

Siesta Key, FL - Casa Berano

JulieRating, 5 stars3 weeks ago
We REALLY enjoyed our stay here! The house was super clean and very well stocked. The pool was very clean and a quiet area back there to relax and enjoy. They had more than enough pool/beach towels and chairs. We loved the location and walkable to beach or a 5 minute drive! The owners are very thorough with directions and information and although we never needed anything, I know they would respond within minutes! Thank you for the warm, spring break at your place! We would definitely stay here again 😎
Guest favourite
Home in Venice
4.89 out of 5 average rating, 182 reviews

Venice Pool Villa with Bikes Kayaks & fun!

LauraRating, 5 stars2 weeks ago
We had a very nice stay here. The house is in a quiet neighborhood, but only 5 minutes from really nice shopping & restaurants, 8 minutes to downtown Venice, and about 15 minutes to the pier on Venice Beach. Host was very responsive and had great suggestions on things to do. Pool and pool area was very clean. Great value.

Family-friendly home rentals with a pool

Guest favourite
Home in Holmes Beach
4.97 out of 5 average rating, 131 reviews

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

MeganRating, 5 stars3 weeks ago
We enjoyed our stay at Kathleen’s home. This was our first time coming to AMI since the hurricane. Kathleen was sure to send updated photos of the interior following repairs. There were still some repairs needed on the exterior (various exposed construction and holes in soffits). However this did not significantly impact our stay. The home was clean and the kitchen was well equipped. We appreciated the natural shower gels, shampoo and abundance of sunscreen. There were numerous beach toys as described and the beach wagon came in handy. The space felt a little tight with two families (with somewhat older children) but would be perfect for young kids given the quantity of toys and activities. We had an issue with the interior locks at one point but this was handled well by the host. Overall we had a nice experience. Thank you!
Superhost
Home in Port Charlotte
4.84 out of 5 average rating, 156 reviews

Waterfront Pool and Dock! Great Family Retreat

IsaacRating, 5 stars16 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 favourite
Home in Bradenton
4.9 out of 5 average rating, 101 reviews

Large Sparkling Clean Pool Home West Bradenton

JesseRating, 5 stars4 days ago
What a wonderful place! I would like to thank the host for providing an exceptional and comforting stay for me and my family. I definitely recommend this place and would return in the future. Thanks for everything!
Guest favourite
Home
4.77 out of 5 average rating, 248 reviews

Tropical Paradise - Private Pool - Close Beaches

PatrickRating, 5 stars3 weeks ago
My family of 5 had a great stay! We loved the home and pool and enjoyed the easy access to AMI either by driving or a short distance to the water ferry! Karin was very helpful with her responses, we would highly recommend!
Guest favourite
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.
Superhost
Home in North Port
4.81 out of 5 average rating, 105 reviews

Well Appointed and relaxing Pool Home

DonnaRating, 5 stars3 months ago
Paul’s house is in a very quiet neighborhood. We found the house clean, the kitchen was well stocked, there were nice beach chairs and beach towels to use and the pool was well heated. The beds were comfortable with nice linens. Paul was quick to respond to our question we had. It’s definitely a place we will stay again.
Top guest favourite
Home in Sarasota
5 out of 5 average rating, 31 reviews

Family friendly with large pool

LauraRating, 5 stars3 weeks ago
Overall, this is a wonderful place to stay. The house provided plenty of room for our family of six adults and two kids. There are several nice features in the home including multiple deck spaces to relax in and a large pool and hot tub. The house was very well equipped and organized. Also, the location was away from traffic noise and advantageously situated on the north end of the Key avoiding the heavy traffic that occurs on the south end. Better advanced communication and more prompt responses to a few issues we discovered upon arrival would have made the experience more enjoyable. In the course of our month long stay we were able to address most of the issues and the host accommodated our concerns. We are planning on staying again next year.
Guest favourite
Home in Bradenton
4.9 out of 5 average rating, 20 reviews

Heated Pool_Hot Tub/Spa_Close To Beaches_Remodeled

DominicRating, 5 stars1 week ago
Great stay! Everything was neat, clean and ready for our stay! Would stay again!

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

  • Total rentals

    1.5K properties

  • Nightly prices starting at

    £45 before taxes and fees

  • Total number of reviews

    21K reviews

  • Pet-friendly rentals

    270 properties allow pets

  • Rentals with a pool

    1.2K properties have a pool

  • Rentals with dedicated workspaces

    690 properties have a dedicated workspace

Destinations to explore