Family-friendly holiday rentals in Longboat Key

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.

Great value!! We loved the pool area and very quiet neighborhood!

This home was the perfect place to stay for our family vacation. Charlie was responsive and provide incredible recommendations anytime we asked. The yard was private and secure and the neighborhood was quiet. The home has everything we needed! We didn't have to travel more than 30 minutes to beaches, delicious restaurants and ice cream. I would absolutely stay here again!

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.

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!

We had an amazing stay at the Bombshell Beach House! The home was spotless, beautifully decorated, and stocked with everything we could need, plenty of towels, linens, and even luxury toiletries. The beds were incredibly comfortable (I bought the same pillows after sleeping so well!). The views were stunning, perfect for morning coffee or watching dolphins. It was a short, easy walk to the beach, restaurants, coffee shops, and boutiques. The pool and hot tub were a hit with our whole family, from our toddler to teens. What made this place truly special was the thoughtful checkout, we didn’t have to take out trash or do dishes, which made it feel like a real vacation. We still tidied up a bit, but it was so refreshing not to have a chore list at the end. Everything about our stay was relaxing, thoughtful, and easy. We didn’t want to leave and are already planning our return. Highly recommend!

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!

Robert was a great host! Lots of great local recommendations. His place was extremely clean and had everything you could need. Well stocked with essentials. Close to Indian Shores Beach and Clearwater Beach. Had chairs, umbrella and cooler to use at the beach, great amenity!! You won’t be disappointed!! Highly recommend to stay at Roberts place and we plan to be back soon!!

Lisa was a great host, and paradise by the beach is an awesome place to stay. My family of 4 (2 adults and our older teens) just loved being able to have a lot of space (compared to the hotel rooms on st Pete beach) and a full kitchen and a close walk to the beach. The kids loved riding the bikes to get an ice cream at night, and it was so easy and convenient to pack up the chairs and umbrella and walk over to the beach. The walk is actually shorter than the resorts we have stayed at on spb. It was kind of like settling into our home by the beach—very comfy and convenient with everything we needed. Lots of tvs, lots of space, easy to get around. I also liked having a fully equipped kitchen—only made dinner one night, but everything we needed was there! We’d definitely again and prefer it to the other resorts we have stayed at. It’s less expensive, more convenient, and a lot more space. Thank you so much, Lisa! We hope your space is available next time we come down!

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.

We loved our stay! The home was just as described. It was very clean and had everything we needed for a comfortable stay. The property is a short drive from first class Siesta Key and other beaches. Romualda was an amazing host. She responded quickly to our questions and went out of her way to make us feel at home. I highly recommend!!

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!!

Beautiful home, lovely host, very close to the beach. Home was very clean and welcoming. Would come back

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!

Great house to stay in and chill by the pool. Location is convenient to restaurants and beach. Ideal for a small vacation getaway. After a long day at the beach it felt good to come into a clean and nice and cold home. Pool was a great after beach treat!

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!

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!

being 7 months pregnant this place was perfect for a quick baby moon! the beach is just a walk across the street, plenty of restaurants less than a 5 minute drive and had everything we needed for the beach as well.

Location nice and private pool/tub perfect for kids

The tropical villas were a great place to stay! Very cozy, clean and my favorite part was how accessible it was to everything. They had bikes for us to use which was amazing, we rode them to the beach each day and then to the town for lunch and dinners and shopping. We also made good use of the beach supplies in the closet. The sand sifter helped us find the most amazing shells and shark teeth! We want to come back here asap, loved it here.

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!

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.

We had a wonderful stay at Ammey’s place. The location was perfect. It was close to all of the restaurants and shops on Bridge Street, it was an easy walk down the beach to other restaurants located right on the beach. It wasn’t far to Coquina Beacb and my husband enjoyed the walking/running path there. The condo was well appointed for our group of 4 people and would easily fit three couples. The extra beach umbrellas you can rent from Ammey were so convenient. There were plenty of chairs and beach toys. I would definitely stay here again on my next trip to AMi.

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.