Family-friendly holiday rentals in Siesta Key

This beautiful, peaceful property allowed for a relaxing few days away from home. We loved our stay!

This is our second year of staying here. Our hosts were very helpful and even left us little treats to welcome us. We arrived on November 8th, 2024. Weeks prior to arrival, they kept us updated on the progress of Hurricane cleanup. Their home is the perfect location. You can enjoy the ocean just across the street or the pool and hot tub with a view of the channel. Their home is clean and includes so many items that would need on this vacation. They were always willing to answer our questions as well as suggestions to make our trip even better. We feel perfectly at home here and can't wait to return next year.

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!

We had a WONDERFUL stay at Chris and Michelle’s place. Private, peaceful, and in a beautiful area. The views from the beach were absolutely stunning and the hosts were incredibly kind and accommodating. The home was perfect for our small family — my three year old had a BLAST and everyone else felt right at home. We made incredible memories here. Much of the island continues to rebuild from hurricane damage, but that did not adversely affect our stay in any way. I was so sad when checkout time arrived! This was our first time in Casey Key but it will not be our last, and we look forward to staying at Chris and Michelle’s lovely home again and again! Thank you for sharing your slice of heaven with us!

This house was everything we wanted and more. Our family had a wonderful vacation and Ven was beyond outstanding to deal with! Communication is huge to me and he is beyond helpful in any situation. 1000000% Recommend. Thank you for a wonderful vacation home!

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.

This place was AMAZING! Beds were comfortable, the house was cleaned and spacious, the pool was definitely a highlight! Highly recommended!

Ulrike's apartment was perfect for two couples. It was very clean and well maintained. The high quality furnishings were comfortable and met out needs. The view was outstanding! Parking under the first floor was a big plus, with an elevator to our floor. We felt safe and had privacy.

This place was perfect! Beautiful and peaceful backyard with a pool, we didn’t get to enjoy it but overall this place was beautiful.

We just wrapped up a very nice one week vacation and stay. Kathleen and her husband were incredibly flexible at both check-in and check-out and they went above and beyond to help us. Throughout the trip Kathleen and her husband were very communicative and they came to the property onsite several times to assist with a few small property challenges that came up which were out of their control. The pool and patio area is the highlight of their property. It is so peaceful and cozy and the pool was the perfect temperature and very well maintained. The second highlight of their place is the kitchen which is by far the best stocked kitchen at an Airbnb we have ever experienced. Third, we very much appreciated the abundance of beach gear and baby/kid gear they have onsite. The setup of the house is slightly non-traditional with some sliding doors to shut rooms off but overall we had a great stay. 5-7 minute walk to beach is accurate. Beds were very comfy.

Great clean place to stay at and they were very fair on price

Our visit for a month with our pup was just perfect. The house was exactly as described and the location was the best. Gillespie Park was beautiful and a great place to walk our dog and there was a dog park. Would highly recommend the house and location. Communication was very good as well for any needs. Thank you for a wonderful visit.

We were new to Sarasota rental and came down for Christmas week as family of 5 (3 adult sons). The place was perfect fit. 2 baths/showers; pool and patio; 5 mins to plazas and 10 mins to key places. Roma was quick when we had questions. Will stay here again.

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.

Great place for a family vacation- privacy, pool and grill means you can relax here, although the beach and village are both quite walkable or a 2 minute drive. Debi & Cage were always very timely and proactive in communications and dealt quickly with any glitches that came up. House was well provisioned and very clean. Highly recommend a stay here.

This rental was so clean and the property owners were always very responsive and friendly. The beach was right outside the door and very clean. The best part was having the beach gear delivered and picked up by a third party so we didn’t have to worry about it. We love AMI and would definitely recommend this property.

Great place and excellent host. Loved the pool and watching the egrets by the lake. Thank you Tomas!

Karin’s place is an absolute tropical paradise! We spent most of our time outside, relaxing on the patio and by the pool. It’s completely fenced in so we enjoyed having our small dog roam around. The inside of the house was exactly as shown in the pictures and it was very clean with everything that you need. The location is fantastic! Close to downtown and many beaches, shopping and restaurants. The property is extremely quiet during the day and night. The host was extremely easy to communicate with and quickly answered any questions we had. It has been a very peaceful stay and we hope to go back someday!

Kim's place was awesome! We loved the outdoor patio and walking in the quiet neighborhood. The beds were comfortable and we had everything we needed. We would book here again.

Janet's place is a lovely place for a family or group of friends. The landscaping outside is beautifully maintained, the interior common areas and bedrooms filled with beautiful pieces of art, the kitchen fully stocked for those folks who like to cook (and the appliances upscale and new), and the bedrooms very comfortable. It is within a 5-minute drive to a Publix, 10 minutes to St. Armand's, and 15 minutes to Lido Beach (which has free parking in the public lot). Janet and Sheila were very responsive with the few things I needed to ask, and very gracious hosts. I highly recommend this home for anyone looking for a SW Florida top-notch vacation.

I cannot say enough great things about the hosts and this place. It was absolutely perfect for our girls trip. Love the patio with lights and a ceiling fan....the beds are comfortable...the kitchen has everything you need. We utilized the washer and dryer a ton and loved the beach wagon and cooler to use for our convenience. These hosts are top notch....I wish I could given them TEN starts. We will be back.......

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.

Great place! Very clean, responsive with any issues. The only huge bummer was there was nothing except towels for the beach (chairs, umbrella, softer, etc) as we’ve had in every other place we have stayed in.

Great clean place in a quiet neighborhood