Family-friendly holiday rentals in Osprey

This is a great house. Immaculately clean. Thoughtful furnishings you dont often see in other rental homes in this area that make staying easier and more enjoyable (e.g., spices, oil, laundry detergent, sunscreen, extra TP, etc,). Just the right balance of furniture - zero clutter but it doesnt feel sterile. Bed in primary bedroom is very comfortable! Lanai is huge and positioned beautifully on a large canal. You could easily never leave the house and just enjoy the amazing pool and lanai. But when you do leave the house, its very easy to get to shops and restaurants. Hosts were incredibly responsive. Thanks for a great stay.

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.

Absolutely loved our stay! The place was spotless, beautifully decorated, and had everything we needed for a relaxing getaway. The location was perfect—just steps from the beach with stunning views and peaceful surroundings. Cindy was incredibly responsive and welcoming. We’ll definitely be back—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!

Roy’s place was comfortable, had good amenities, good location ( multiple beaches and restaurants in a close radius). The house was beautiful and just as described. The pool/hot tub, and outdoor seating was private and well maintained. Chairs, umbrella, and cooler were available to use which was a nice plus. We would definitely love to stay at this place again. Roy was quick to respond to any questions we had.

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.

Loved our stay - the house came with everything you might need and having access to the pool, tennis courts, etc was amazing! Feels like a private resort. Highly recommend!

amazing! would repeat again 🤩🤩

A beautiful place on the gulf with everything you need for a relaxing beach getaway. Really enjoyed it

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 place to stay, very clean, spacious, nice pool area and lovely trees/flowers surrounding the pool.. fully equipped kitchen with all and more that is needed during a stay…would recommend.

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

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.

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

We had an absolutely wonderful stay at Sheila's place! The location was perfect, close to everything. Sheila was incredibly responsive and helpful throughout our stay, answering all our questions promptly. We highly recommend staying here!

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 home was a good distance to all places me and my group ventured off to. The home was clean and Sheron was amazing at responding. Would absolutely recommend to stay here :) Thank you Sheron !!

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.

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!

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.

Great home, close to the beach and had a ton of fun.

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