Holiday rentals with a pool in Osprey

I had a wonderful stay at this beautiful home! The house was spotless, stylish, and had everything we needed for a comfortable visit. The pool was definitely a highlight — clean, well-maintained, and perfect for relaxing. The whole place felt peaceful and welcoming. I would absolutely stay here again and highly recommend it to anyone looking for a great getaway.

Marilyn was very responsive when I needed her, and the place looked exactly like the pictures posted. It’s only 8 minutes driving to Nokomis Beach and same for Downtown Historic Venice where you can find all the good local places to eat and buy gifts, as well as Venice Beach at the end of downtown . Publix is very close if you need to buy groceries. Everything was provided at the house, even things for the beach. The house was beautiful and the location was great and quiet. The pool didn’t disappoint. My grandkid loved it . We all did. I recommend 100% this place! Spacious, clean, beautiful and convenient. If it’s available in the future I will stay here again.

We had an amazing stay at this beautiful home in Venice Beach! The house was clean, stylish, and had everything we needed—and the private pool was the perfect bonus for relaxing after a day of exploring. The location was great, close to everything but still felt like a peaceful retreat. The host was incredibly kind and responsive, making sure we were comfortable and had everything we needed. We’d absolutely stay here again and highly recommend it to anyone looking for a great getaway

The hosts were very responsive and very helpful. Their home was spotless. The pool with the enclosure allowed you all the sunshine you could ask for without the bugs! The interior is very spacious and great for hosting dinner. With the turf back yard it’s the perfect hangout for adults and children! The hosts are very thoughtful with items available for the perfect beach day (beach wagon, chairs, a cooler, and lots of fun items for children! We will definitely be visiting again!

We had a great stay at this property. Seaglass Management was always responsive and accommodating. The house was clean and the backyard was large and well maintained. The only downside was the bathroom situation. There is no master bathroom and one of the bathrooms for the house is really a 3/4 bath. For 8 adults and a baby the bathroom situation was a little difficult, but we made it work.

The house was tucked into a quiet residential community. The home was clean, fresh and spacious. The guest house area with its own bathroom is perfect for a two family stay! The neighborhood was safe to walk in- I walked daily. The neighborhood was really within 15 minutes drive of anything we wanted to do. We spent most of our time at Siesta Key! Leave EARLY for the beach, if that's your day's plan! We would definitely stay again!

We had a wonderful stay at this beautiful home in Sarasota! Everything was clean, comfortable, and just as described. The house had a peaceful atmosphere, a great layout, and was well-equipped with everything we needed. One of the highlights was the amazing pool and the fantastic BBQ area — perfect for relaxing and enjoying the sunny weather. The neighborhood was quiet and safe, and shops and beaches were just a short drive away. Highly recommend this place to anyone looking for a relaxing and cozy stay. Thank you for hosting us — we’d love to come back again!

Max’s place was perfect for our vacation! The house is beautiful and the pool is a wonderful addition. The beach is just a short drive and they even had some beach accessories for you to use if needed. I would highly recommend Max’s place for your vacation!

Excellent place, unbeatable location, very cozy and comfortable. Chris let us know we could check in early without even asking. I would gladly come back!

Had a great stay and everything was as listed. Clean and convient, quiet location, 5 minute walk to the beach. Was located right across from both pool and laundry room (quarters only) which was great. William also provided beach chairs and umbrella as well as small cooler which was exactly what I needed

This is our second year staying here. It was wonderfully peaceful this last weekend, just like last year. The beach is less than two minutes walk from the door. The kitchen had everything we needed in it. Plenty of beach items for use in the closet. The bathroom had more than enough towels and TP. We also used the pullout couch for our children, and they were very comfortable. we hope to book again soon, thank you!

This was the most clean, most relaxing, most safe feeling place we've ever stayed in through Airbnb!! Thank you so much for such a wonderful experience. We would recommend 10/10 to anyone!!!!

Great stay, the location, the amenities all were wonderful. Melissa and Brandon were super responsive and the place had more essential stocked than most of the other places we have stayed, which was very thoughtful. Melissa also had a regular coffee pot sent out to us right away, since we don’t use Keurig’s which was super nice and very much appreciated. We would definitely come back!

My fiancé and I really enjoyed our stay at David’s place in Bradenton! The space was super clean and had everything I needed for a comfortable stay. Communication was excellent throughout; the host was responsive, helpful, and always timely with their messages. One of the best parts was the beach access—super convenient, and the place was stocked with everything from a beach cart, umbrellas, chairs, and beach towels etc. which made days at the beach so easy. There were also a few great local tips provided, which I definitely took advantage of. Honestly, I wouldn’t change a thing. I’d absolutely stay here again and highly recommend it to anyone visiting the area. Thank you for a wonderful stay!

This condo was everything I needed and more! The location? Absolutely perfect—the beach is literally your backyard. Waking up to that ocean view the next morning was a dream. Restaurants and activities were just minutes away, which made everything so easy and fun. Heidi, the host, went above and beyond. Her communication was fast, kind, and incredibly thoughtful. She even surprised us with a delicious key lime pie and orange juice waiting for us after jet skiing—such a sweet and personal touch! I truly have no complaints. Everything about this stay was peaceful, beautiful, and seamless. I’d absolutely recommend this spot to anyone looking for a relaxing and magical beach getaway. 🌴🌊💛

Another wonderful trip to Siesta! This is our third stay in one of Evan’s places, and we were not disappointed. This unit had a great view of the Gulf (this particular building has the most direct view, without the parking lot!), and the screened in lanai was amazing! As always, the unit was clean, well-stocked, and a perfect home away from home. Already counting down the days till we return!