Family-friendly holiday rentals in Sarasota County

Marc and Dave were incredible. They were responsive and proactive! I will definitely be back. We had a family of 7 and even though it was small, we were comfortable. The bikes were an added bonus and amazing to use for our trips to the Daiquiri Deck! Although the weather didn’t cooperate we still had an amazing time and would 10000% recommend this place. Traveling with 5 kids can be stressful and they made accommodations seamless!

Just returned from another great stay at Kayla’s place. Everything was fantastic, the backyard pool and jacuzzi were amazing. We also really appreciate Kayla’s responsiveness. Looking forward to returning next year!

Super clean, quiet, comfy bed. We enjoyed the bayside pool. Nice views. Palm Bay club nice benefit as after a short walk over to the beach we enjoyed the chaises delivered and set up close to the water and hole drilled for our beach umbrella. Amazing sand is not over rated. Warm gulf waters and easy entry and exit. Breeze Trolley with their app made getting around without driving convenient . Lots of fun food and shops minutes away. This bayside spot a was a delight.

This was our second stay in this stunning home. Jennifer and Amy were excellent to work with. They respond to communication promptly and authentically cared that we had the perfect stay. The home is beautiful and had everything we needed. My husband and I are already talking about returning. Highly recommend!!!

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!

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.

From the moment we arrived at this top-rated “Quaint Cottage,” we knew we’d found something special. This charming retreat sets the bar for excellent stays. Inside, every detail felt outstanding—from the freshly laundered linens and plush towels to the fully equipped kitchen that made cooking a breeze. Madeline’s communication was first-class, offering clear check-in instructions and local recommendations that turned our weekend into a seamless escape. Every little touch—from the high-speed Wi-Fi to the thoughtful supply of beach chairs and umbrellas—was superior… the gold standard of hospitality. Location-wise, you couldn’t ask for more: just a quick four-minute stroll to Crescent Beach’s powdery white sands, turquoise blue water and deep red, yellow and orange sunsets. Within steps you’ll find a lineup of dining options—fresh seafood at waterfront restaurants, laid-back bars serving sunset cocktails, and cozy cafés perfect for post-beach coffee. In every way, our stay was awesome!

I had the pleasure of staying here with my family and dog, this beautiful home was very well supplied from kitchen to the bathroom, living room the decor in the home is beautiful the welcome flowers and note, in Awe! . My kids loved to play the putt putt and go in the jacuzzi, they were not brave enough to do the cold plunge but I was able to conquer it and it was great! The rooms and beds were comfortable, I loved that this home was pet friendly and had a doggie bowl out and ready the house was GREAT! We love that it was 15 minutes away from everything we did and the beautiful beaches. All in all it was an amazingly beautifully put together home that left my family and I with ideas of decor to backyard ideas. Erinn was a wonderful host and is quick to respond when you need her. Thank you and we plan to hopefully come back again in the summer.

It was a pleasure through the entire process.Unfortunately we had an emergency and weren’t able to stay,but the check in and communication was fantastic.Would definitely rent again

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.

What a beautiful home! It had all the comforts and convenience of being home. Jane was very responsive to any questions we had.

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!!

Great area and lovely room. I ended up getting sick my first day of vacation and spending a lot of time inside and in bed but thankfully the bed was comfy and the apartment was cozy and clean. Would highly recommend!

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

We thoroughly enjoyed our stay. The house was a private and calm place to come home to after our long beach days. We enjoyed spending our nights out by the pool. The pool lights we a nice touch. Would recommend to those who enjoy being in a quiet area.

Excellent host! Would stay again! Great location and great home!!

We had a very good time at Siesta Key and enjoyed our time at Maureen's place. The building is older, the amenities are well maintained and the condo itself is well cared for. I did find some mystery stains on the mattress and the decorative pillows in my room, but I'm guessing they are just spills that were difficult to get out. More importantly, the boat dock is usable, albeit with some difficulty if the boat is larger than 22 feet or so. We figured out on the second day that the best way to dock was parallel to the intracoastal between the posts and to tie off with lines on either side of the stern and with a single line on the bow. I would check ahead to make sure the dock is available, but we had no other boats docked there on a holiday weekend. The private beach access was a lifesaver on a holiday weekend, despite the short walk required to get there. Having both intracoastal and beach access is the biggest value of the place in my opinion.

Absolutely love Sea Club. This was our second stay there. Will always come back. Walk to the beach is not bad at all. Condo is next to the road but still quiet. Really enjoyed our stay!

Fantastic location! Easy to walk to restaurants and there is also a free trolley if you do not have a car. The room was very clean, well equipped, and perfect for our five day stay in Siesta Key. The designated parking spot was a plus because parking is at a premium. I only needed to talk to Bernadette once and she was very quick to respond. We will definitely be coming back! My only complaint is we couldn’t stay longer.

It was lovely! Perfect distance from downtown as well as the beach! Beverly was super helpful and flexible. She responded to everything and immediately looked to accommodate us! Would definitely recommend.

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.

Can’t say enough great things about heather &Steve’s place. House was beautiful and perfect for our family. Short drive to the beach and tons of restaurants and shopping. We had a great time and hope to be back!

nice place to stay close to beach and right across from trolley pickup

Our family just spent an amazing 4 days at this wonderful place, and let me tell you, the location is simply unbeatable! It's a charming, no-frills home just a stone's throw away from the beach, making it perfect for sun-soaked days and seaside adventures. Just a heads-up for those sensitive to noise: it’s close to a lively street, so light sleepers might want to keep that in mind! Also, while the property doesn’t provide essential items like bathing soap or shampoo, it does include hand soap and dishwashing soap, which is super convenient. Plus, with a supermarket and a Seven-Eleven right across the street, you can easily stock up on anything you might need. And let’s not forget about our host, Thomas! He’s incredibly responsive and an absolute superstar. I would jump at the chance to return to this fantastic property if it’s available again. Don’t miss out on this gem!