Family-friendly holiday rentals in Sarasota County

It was a nice clean place. I would definitely stay at Robert's place again. It right around the corner from St. Armands Circle and close to beach. They had everything you need for your stay houseware and beach stuff.

Can’t say enough good things about the house and Steven. The house was beautiful, it was everything we could’ve wanted and to have the additional beach supplies readily available was amazing! Steven answered so quickly and was happy to help however he could. 10/10 for us!!

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!!!

Our stay was amazing, Ven was a great host, unfortunately there are always minor issue that come about when staying in properties but their communication was so great it over shadowed all of our concerns! Thank you for the stay!

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 love love this place. What a beautiful peaceful house. I rented the house for me and my daughters, we had an amazing time there. The house comes with everything you need for a getaway. It’s close to so many beaches, restaurants, shopping and grocery stores. Only 15 min away from my favorite beach which is Lido Beach. Erinn is a lovely host, communicating immediately and extremely friendly. I would definitely stay here again :).

This cottage was perfect for me, my husband, and our baby girl. We had the pool to ourselves the whole time, which isn’t guaranteed but was great. Weather was perfect. The beach is so close and so nice. The area has beautiful, large homes, which made for nice scenery when we walked. I really liked the location of this place vs the north end of Siesta Key. It was less crowded and very easy to navigate places. Dave, the property manager, was amazing. He was very informative, friendly, responsive, and helpful.

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

This is our second stay at this beautiful home. It is in a wonderful neighborhood and is very quiet and just a great place to unwind. I highly recommend staying here the home was very clean and has everything you need just bring your clothes and food and enjoy the pool! Darcy is wonderful and will definitely be booking 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.

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!

We had a wonderful time in Sarasota. Maureen and Patrick are clearly hosting pros. The kitchen was well-stocked, so we cooked most of our meals, made coffee/tea in the mornings, and kept groceries from the nearby Publix in the fridge. We enjoyed making dinner and sitting out on the screened in porch. The neighborhood was very residential and safe. The bathrooms and bedrooms were well-stocked and comfortable. Five college girls slept comfortably across the three rooms and I would say one more could definitely have fit as well. The house had a carport with a washer and dryer with detergent, beach chairs, umbrellas, and puzzles. Even when it rained, we enjoyed sitting in the house and reading because the space was relaxing and comfortable If you’re planning on going to the beach, download the Bayrunner/Breeze Rider apps to catch the free trolley. The trolley was a short walk away through the neighborhood and we enjoyed riding to the beach every morning.

This was our second time staying at Lubos pool house. We really enjoyed our stay and are already looking far time to escape back. Great location near restaurants, stores and beaches. Back yard and pool are a dream and very peaceful.

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.

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.

This place was perfect for two couples and close to the beach etc The beds were comfortable and check in and check out easy. We would stay here again

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!

The house was really great as were the hostesses. There were a few things like the air having to be set to 73 and no lower that seemed a bit odd for a summer day in Florida, but there were a ton of ceiling fans that helped keep things cool. The back yard and pool were a perfect little escape and it was a quick uber ride to some nice restaurants. If you want to be walking distance to the beach/water this may not be what you are looking for but Siesta Key is still less than a 20 minute car ride. Overall I would definitely stay with this group again. Instructions were clear and responsiveness/attentiveness was on point!

I enjoyed my stay. David is very responsive and gives detailed instructions on how to get into the house. The area is convenient, the neighborhood is peaceful, and the unit is clean. I recommend booking this place!

We really enjoyed the Drift Inn Unit B! Our family of 4 felt right at home and comfortable, with enough room for all of us. The condo looked like the pictures and had all the listed amenities. We utilized the washer and dryer, and the included beach gear was a great plus! The shared pool was very nice and clean, and the location of the house was just perfect! It felt safe and secure and was quiet and private, even though it was on the main drag of the little community. It was awesome having the beautiful beach a 3-minute walk in one direction; and little shops, stores, restaurants, and bars just a few minutes walk in the opposite direction. We did not have to contact the host during our stay, but he sent very clear and helpful check-in/check-out instructions with plenty of time before our check-in. There was even a little book at the condo with additional information. I can’t say enough good things about we really enjoyed our time here and we hope to come back!

I had a few questions at the beginning and Gregg responded promptly. The house was neat and tidy, loved the quietness of the neighborhood. We enjoyed the wildlife I even brought my binoculars lol, The kids & I got to see a baby gator. We enjoyed the pool and the weather was great. Definitely will be back… Thank you

We greatly enjoyed our stay at Chip and Miao’s place! It was comfy, spotless, and had everything we needed! The beach cart with the chairs and umbrellas were so nice to have, and it was a short walk across the street to the beach! The bed was super comfy and everything just felt clean and new. We had to change our dates a few times and Chip was super lenient with us and quick to respond. One of the chairs broke on our last day and he was super quick to respond then also and even offered to bring us a new one! We will definitely be back!