Vacation rentals with outdoor seating in Osprey

Great location, clean and cute. A great size for a large or small group of people

My family and I had a great stay during our spring break. We had our 3 kids (ages 2, 7, and 12) and they absolutely loved the pool and hot tub. The house was very clean and the beds were comfortable. Several beaches nearby on Anna Maria Island. We will definitely be back and our kids already want us to plan our next vacay here. Thanks Jen and Brittany 💕

This house was perfect for our family! Clean, homey and had everything we needed. The pool was our favorite part and Carolyn went the extra mile to turn on the heater for us… thank you so much! You can tell that they take pride in having a clean house…. Spotless! We hope to stay here again!

Kathleen thought about everything! She went above and beyond to make sure we had everything we could possibly need during our stay. The property is recently renovated so a lot of things were new. The location was great and the house is located in a nice, quiet neighborhood. One thing to note is that one room has thick curtains instead of a door. It wasn’t a problem for us, but just mentioning it so people are aware. Would definitely consider booking Red Door Siesta again!

This home is perfectly located for all beach and ocean activity. It was extremely convenient to our activities. It is located in a quiet neighborhood and yet an easy walk to many activities, restaurants, shopping. The interior of the home has been freshly done and was easy to use. The pool was especially perfect for our family’s use. It was a delightful home in all regards.

Great host and house. We enjoyed the layout of the house, awesome kitchen but the most we enjoyed the outside space and pool. Very nice neighborhood for walks in the morning. Easy drive to beaches, quick drive to grocery stores and restaurants.

Absolutely perfect! So many beautiful words come to mind to describe Edward and Tatyana's exquisite home. The pictures capture only a glimpse of the true experience we had. Brimming with charming details and unique touches, the house left us yearning for more time to explore. Our family of eight reveled in the joy of shared moments and laughter. The idyllic location, surrounded by serenity, provided a peaceful retreat, while the gracious hosts radiated warmth and kindness. We can not wait for our return to this beautiful home.

We loved our stay here. Chris was super responsive and flexible with the check in time. The house was only 10 minutes from the beach and all the local restaurants. There is also a Publix less than a mile from the house. We would definitely stay again.

My husband and I had a wonderful time staying here for a week. Place was nice and clean. Had everything we needed. This place is right outside Downtown Sarasota and only about 15 minutes from Siesta Keys. Lisa was a great host. If ever back in Sarasota we would definitely stay here again.

Great location, and spacious for 2 people.

Location is always the key, and Jesse's place its just perfect. 3 Min walk to a delicious French Cafe, restaurants. Excellent parking and I really like the little work station!

Good location and host was accommodating.

Dan and Charles place was perfect in every way! We cannot say enough about their place and them! Location couldn’t have been any better. We’ve been coming to Sarasota for 3 years now and this place was at the top of our list.Don't hesitate, book it now!

I stayed two nights at this beautiful oasis and it was fantastic. I’m a local but I wanted a little staycation and this is perfect.

We loved staying in Peter and Pearl's unique and artsy home! They have thought of everything anyone could possibly need for a short or extended stay in one of our favorite places - Sarasota. Their home exceeds above and beyond all expectations of what an Airbnb/VRBO should be. My husband and I would definitely stay here again!

My family enjoyed a week long Spring Break trip and felt very comfortable with the location primarily. This is our fourth year at Siesta Key and it is a safe and family friendly environment. I feel secure in allowing the kids to walk to the village and they know their way around as well. The beach is right across the street which is wonderful. The pool was private and not overly crowded with other guests. The den that is converted to the third bedroom is not very private, however we brought an extension curtain rod and long black out curtains to close off the room. It worked perfectly. My biggest complaint would be the temperature of the condo. The thermostat will not go below 73 degrees and to be honest it tended to get pretty stuffy in the condo. It would have been ideal if the temperature was cooler for our comfort level. Overall, we had a fantastic trip.

The location - right on the beach - is superb. Great covered porch looking right out on the beach. The unit has some of the things to help spend a day on the beach - chairs, umbrella, etc. the kitchen is small but entirely sufficient and well stocked with kitchen/dining things. Comfortable bed. Plenty of closet and drawer space. Really enjoyed my stay at the unit and in Englewood.

This lovely condo was as described and pictured. Comfortable furniture, clean, well decorated to encourage relaxing. Maureen was friendly and kind. Was a super peaceful and relaxing visit to beach!

Perfect stay for my family! It had everything we needed and more. The beach chairs, mats & cooler made our beach days more enjoyable. Washer and dryer worked great and kitchen had everything we needed. We didn’t have time to use the paddleboard but it’s an awesome bonus. We would definitely stay again!

We just had a perfect five night stay and couldn't recommend this place more. The location was beautiful with a peaceful, private balcony but also close proximity to the pool. The condo was stocked with everything we could possibly need. We were traveling with a three year old and were delighted to find all of the things to make a beach day safe and comfortable already there (chairs, toys, puddle jumpers, etc.). We were so comfortable and relaxed and felt right at home. The condo complex felt clean and safe and everyone we met was super nice and friendly. The pool area was clean and never crowded and we spent a ton of time swimming and relaxing in the hot tub and e joying the beautiful atmosphere and views. We hope to go back soon and absolutely would recommend Summer's place!

great place to stay...room was clean, very short walk to the beach, many items in the room available to use (numerous beach chairs, beach umbrellas, life jackets, ect) would definitely stay again!

Was only able to book a short stay, but I couldn’t say enough good things about the experience. Great area, perfect beach front location, clean & tidy space & wonderful host. 10/10 would recommend to anyone looking for a place on the gulf!

We are already looking to see when we can come back to Florida and stay in Daniel's rental again! It has everything you need, it is well-kept, and it is close to everything you want/need (the beach, Detwiler's, Publix, stores, restaurants). It is in a safe location. The Shorewalk ammenities (pools and hot tubs) are nice as well. Even though one pool's heater was broken, there was another pool to choose from and two hot tubs. He checked-in with us to make sure check-in went well and to make sure that our stay was going well. Daniel provided thorough instructions and recommendations for everything you could possibly need. He was a great host with a great home away from home!

Our stay was very relaxing & enjoyable. Beautiful views, great location for walking ( nice walking/biking path), appreciated the pickle ball equipment so we could use the pickle ball courts on site. The pool was very nice, great being able to use a grill too. Condo is absolutely beautiful and comfortable. Had everything thing we needed. Other than getting a little warm at night, we were very comfortable. Loved the access key system to enter Condo, by far the best we've ever experienced. It was so nice having beach towels, beach chairs, all of the little supplies you need that often times you don't have at other places. Thank you so much for our stay!