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Family-friendly holiday rentals in Longboat Key

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Longboat 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, 140 reviews

Gorgeous Home / Heated Pool and Spa

svitlanaRating, 5 stars2 weeks ago
Another great stay at this house! Love the location, very clean throughout, has everything you would need and more. We spent most of our time in covered outdoor area which has lots of seating options, the pool/hot tub is perfect! The only small issue we had was the door to the pool does not lock securely, therefore adding a safety risk if you have young children. It needs to have an added safety lock on top or something to that nature.
Top guest favourite
Home in Clearwater Beach
4.98 out of 5 average rating, 120 reviews

THE HOUSE - 32 Steps to the Beach - Beautiful Clearwater Beach Home just across from the Beach - Drive to your door.

LaurenRating, 5 stars5 days ago
We had a great time staying here in Clearwater. SO close to the beach. Their place was clean and was ready for a family to stay. We look forward to coming back.
Top guest favourite
Home in Tarpon Springs
4.96 out of 5 average rating, 363 reviews

Tarpon Fun'n Sun-Pool, Beaches + Backyard Chickens

DavidRating, 5 stars5 days ago
Beautiful house and pool area. The back is private with plenty of space. Jeff was always responsive and everything was as described. The girls being able to get eggs every morning was an added touch of experience for them. The house was clean and we had everything we needed for the ten day stay. Tarpon Springs is an annual tradition and we weren't disappointed.
Top guest favourite
Apartment in St. Petersburg
4.98 out of 5 average rating, 269 reviews

PRICELESS VIEW Boca Ciega Bay Condo 1/1 #209

KathrynRating, 5 stars1 day ago
Cozy little place, well decorated and clean. Bed was comfy. The pull out bed was good enough for my 6 yr old, but would recommend bringing a pillow for it if you’re going to use it. There isn’t one in the room for it unless you use the main bedroom pillows. We beached most of the time and didn’t watch TV, but if we wanted to the couch wasn’t comfy for lounging around. We loved the balcony though! The only “complaint” would be all the coffee supplied was decaf and it was a shock the first morning after getting in super late. So, bring your own coffee just in case. Host was super helpful when there was any other issues. Very kind and accommodating! Plus they supplied plenty of TP and PT, beach towels and towels. Can’t wait to come back!
Top guest favourite
Townhouse in Clearwater Beach
5 out of 5 average rating, 122 reviews

Waterfront Beach House Steps Away from #1 Beach!

MariannaRating, 5 stars3 weeks ago
We absolutely loved this space! We do an annual girls trip to Florida and we were so incredibly happy with the house, layout, amenities, cleanliness and location. Instructions were clear and posting is exactly as described. Can walk to everything in Clearwater from here. We cannot wait to go back!!
Guest favourite
Apartment in Indian Shores
4.94 out of 5 average rating, 105 reviews

Bay Shores Yacht & Tennis Club Indian Shores FL

AndreaRating, 5 stars3 weeks ago
Great location! Easy walk to the beach. Property has desired amenities. Inside had everything we needed.
Superhost
Apartment in St. Petersburg
4.86 out of 5 average rating, 465 reviews

Waterfront condo on top floor @ Boca Ciega Resort

AileenRating, 5 stars2 weeks ago
The condo was just what we were looking for. The kitchen was equipped with the basics and the view was wonderful. Tamara was friendly, responsive, and a great host. Would stay at her place again!
Top guest favourite
Flat in Dunedin
4.99 out of 5 average rating, 244 reviews

Tropical Paradise

NancyRating, 5 stars2 weeks ago
Perfect oasis for a tropical getaway! Everything was just as described. Really enjoyed the use of bikes and Honeymoon Island is absolute paradise! Lori ands Gary were very attentive and quickly handled anything we needed!

Family- and pet-friendly home rentals

Guest favourite
Flat in Bradenton Beach
4.9 out of 5 average rating, 126 reviews

Newly Remodeled Beachfront Studio - On the sand!

AnnetteRating, 5 stars1 week ago
Jeffery’s rental was perfect. He has such an eye for detail and it’s beautifully decorated. Our view of the ocean from the sitting area outside the rental was spectacular! The space contained everything you would possibly need and was extremely comfortable. This is our second stay at Shell Cove 1 and we highly recommend it to others.
Guest favourite
Home in Sarasota
4.95 out of 5 average rating, 212 reviews

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

YanyRating, 5 stars1 week ago
La casa estuvo muy acogedora, limpia y cómoda. Había todo lo necesario para ir a la playa, sillas, toldo, toallas, cava… Estaba a muy poca distancia de la playa y de otros lugares de interés. En la cocina tuvimos incluso más de lo que se pudiera esperar para este tipo de alojamientos, por lo que, te podías sentir como en casa. La piscina estaba realmente limpia. En cuanto a este último punto, les recomiendo que sean más claros en cuanto al horario de uso de la piscina y de la BBQ. Entendemos que es un vecindario tranquilo, sin embargo, también deben considerar que no todos los huéspedes son personas ruidosas, también viajamos familias y personas decentes que respetamos las reglas, pero el anuncio debe ser claro y honesto para que uno pueda decidir correctamente. Dicen que las luces encienden y apagan automáticamente PERO NO DICEN QUE UNO NO TIENE CONTROL SOBRE ELLAS. Llegamos de la playa luego de ver el ocaso 8:30PM a hacer BBQ y de repente todo quedó oscuro ESO ESTUVO MUY MAL.
Guest favourite
Bungalow in Rosemary District
4.87 out of 5 average rating, 131 reviews

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

JacquelineRating, 5 stars1 month ago
This place was a great home away from home for the week! It was clean, comfy, and cozy. It was in a great location, being about a 10 minute walk from some of the best local restaurants, and about 15 from downtown! We found a great breakfast spot I would highly recommend, called The Breakfast Company. Would definitely stay there again!! Great price and Erin was a great host with prompt and helpful responses when needed!!
Top guest favourite
Home in Seminole
4.97 out of 5 average rating, 194 reviews

4BR/3BA Pool Home 7mins to Madeira Beach-Sleeps 14

BenjaminRating, 5 stars4 weeks ago
For those traveling to the area, this is the perfect spot! My family and I had a wonderful time and Stephanie and team were always there if we needed anything! Home is very close to the beach, plenty of places to sleep, beautifully designed, and in a great neighborhood. Would definitely plan to stay here again!
Superhost
Home in Sarasota
4.83 out of 5 average rating, 260 reviews

Private Siesta Beach House Oasis with Heated Pool.

AlfredoRating, 5 stars4 days ago
Great place, we enjoyed the house so much, my wife and I really enjoyed it but our 15 yr old dog got a post vacation depression after being at this house. He was so happy and so were we. Great location, the house has everything you need to disconnect and enjoy few days by the pool. Andrew is a very quick responsive host. Perfect place, perfect days!
Guest favourite
Bungalow in Indian Shores
4.9 out of 5 average rating, 205 reviews

Private Beach Bungalow 1BR *Heated POOL**PETS ok

Josh and Sarah Rating, 5 stars3 weeks ago
We recently wrapped up an AMAZING stay at The Lobster Beach Bungalow. Everything was as described- charming ‘old Florida’ feel and close proximity to the beach (50 steps). It felt like a miniature resort. We got to meet other vacationers staying at the other bungalows, which was pretty cool. We were even able to enjoy the pool on a day where the gulf waters were a little rougher. There are a lot of eateries within walking distance. We tried a different coffee shop every morning- yum! The bungalow itself was comfortable and had everything we needed for a great stay. The kitchen had we could have desired should we have decided to eat in. Too many yummy local eateries for that for us though! We also loved being able to have our fur babies with us, as no vacation is complete without our whole family. We look forward to returning next year with some extended family to experience this peaceful paradise. Thank you, Liz, for creating a place that feels like home away from home!
Top guest favourite
Home in Sarasota
4.97 out of 5 average rating, 100 reviews

"Chill Time” Great Location in Sarasota

AlexRating, 5 stars3 weeks ago
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!
Top guest favourite
Guest house in Sarasota
4.87 out of 5 average rating, 415 reviews

The Cottage, very close to Siesta Beach!

PaulRating, 5 stars3 weeks ago
Fair price. Great Location. Awesome / quick communication.

Family-friendly home rentals with a pool

Guest favourite
Home in Anna Maria
4.9 out of 5 average rating, 59 reviews

Island in the Sun, luxury beach house,private pool

JamieRating, 5 stars1 month ago
Had the absolute best stay here! Everything was perfect, from the interior design to the location. The pool was great with lots of privacy in the backyard. The house was spacious, each bedroom having a king and its own bathroom. My son loved that. We would love to stay here again!
Guest favourite
Home in Sarasota
4.88 out of 5 average rating, 156 reviews

5 minutes to private Siesta Key Beach + 2 pools

DonnaRating, 5 stars1 month ago
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!
Top guest favourite
Home in Siesta Key
5 out of 5 average rating, 144 reviews

Beach, Village, Dock & Private Pool! One-of-a-kind

ZacharyRating, 5 stars1 month ago
Marko’s family home was beautiful, charming, and spotlessly clean. The home is perfectly located, walkable to beautiful beaches and great restaurants and shops, including the market. Marko was extremely hospitable, ensured we were all set and gave wonderful recommendations. We loved this place and will be back again next year. Thank you!
Top guest favourite
Home in Bradenton
4.99 out of 5 average rating, 100 reviews

Pickleball | Heated Pool | Game Room | 4 Min to Be

OmarRating, 5 stars6 days ago
We had a great time. Super clean, beautiful home, full of extras. The property has many things to do and keep everyone entertained. Great communication, definitely one of our favorite vacation homes. Can’t wait to stay here again!!!
Guest favourite
Bungalow in Indian Rocks Beach
4.88 out of 5 average rating, 121 reviews

Tiki Bungalow | Gorgeous Htd Pool | Steps to Beach

GregRating, 5 stars1 week ago
We were looking for a quick family vacation at the Gulf of America and we found this little gem at Indian Rocks Beach. The location was perfect and only 30 min from the airport. With all equipment provided to be at the beach and only a short walk across the street, it was just what we needed. There's a cool little ice cream and sandwich shop right across the street Kooky Coconuts offering the best Cuban sandwich in Florida and great ice-cream. Sleeps 4 comfortably and has a great tiki bar in the back. If your looking for relaxation, great restaurants and beach, this is the place. Owners are awesome and where always available if we needed anything. Definitely will be back!
Superhost
Apartment in Longboat Key
4.86 out of 5 average rating, 99 reviews

Sunset and beach view from your balcony Unit 403

NickiRating, 5 stars2 months ago
This place was just what we needed for some rest and relaxation. Everything was exactly as listed. Extremely clean and well supplied with towels and all your kitchen needs. The views from our balcony and the sounds of the ocean were priceless. If you’re looking to get away from it all and disconnect, this is the place!! You will not be disappointed.
Top guest favourite
Home in Sarasota
4.98 out of 5 average rating, 105 reviews

SIESTA BEACH HOUSE HEATED POOL☀️🌴3 MIN TO BEACH!!

MattRating, 5 stars2 weeks ago
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.
Superhost
Apartment in Indian Shores
4.92 out of 5 average rating, 159 reviews

1 BR direct gulf front!

SusanRating, 5 stars6 months ago
Due to the hurricanes there was still some work going on at the Condo and on the beach. We completely understood and knew this might be the case coming in. Our goal was to relax and unwind and that is what we did! We loved the location - the ocean view from the deck and the short walk to the beach. The bed was relatively comfortable - not too hard. There were plenty of things in the kitchen to make using it easy. We walked and hung out on the beach a lot which was our plan. The pool is small but was nice. There are restaurants and stores within relatively close driving distance. When we had a question everyone was quick to get back to us. Overall a truly wonderful experience!

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

  • Total rentals

    690 properties

  • Nightly prices starting at

    ₹4,327 before taxes and fees

  • Total number of reviews

    5.8K reviews

  • Pet-friendly rentals

    110 properties allow pets

  • Rentals with a pool

    600 properties have a pool

  • Rentals with dedicated workspaces

    240 properties have a dedicated workspace

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