Vacation rentals with outdoor seating in Downtown, Sarasota

Fantastic Airbnb! Seaglass Management and Joy are great to work with. Very responsive! Great location, very safe, amazing pool and jacuzzi, close to downtown, restaurants and the Legacy bike trail. Will definitely book again in the near future.

This spot was perfect! We traveled with our two young children and parents. Having the two separate spaces made the whole vacation a breeze. The pool and outside area was beautiful. Any questions we had were quickly answered and we will definitely book this spot again when we come back. Close to everything but very private!

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.

Our stay at Wanda’s listing was wonderful! It was a very nice home with lovely decor, and we felt right at home! Very comfy beds and well-appointed bathrooms. Thank you, Wanda!!

Stayed in many places in Sarasota and this one takes the lead!!! Will definitely stay again!

This home is Beautiful! Well taken care of and spacious. The pool and the esthetics are so nice. Just as the pictures. The home is well equipped in the kitchen with utensils and seasonings as well as the bathrooms. James was very responsive and accommodating to our needs before booking. Very kind host. So glad we went with his home. Don’t hesitate. Book this home. You will love it.

My husband, son and I loved staying at this gorgeous property. The interior is adorably decorated and very clean and the outdoor space was perfect too. The pool was such a great addition to this house, my 4yo son has been asking to go back to the “pool house” since we left. We’re already checking schedules to see when we can come back for another visit. The location is great too- very close to siesta key beach, the village and all of the local amenities that Sarasota has to offer. I cannot rave about this property enough. I can’t wait to come back for another visit!

It was a great experience. We were there for the rowing national competition. It is an easy drive to the park, and a nice residential neighborhood. The apartment is well equipped and very clean. I highly recommend!

This was our second time staying at your condo. Once again, we really enjoyed ourselves. We really appreciated the fact that you had two regular beach chairs for us to use. We had a wonderful time once again. Everything was just perfect.

This location is halfway between coastal attractions (beach and downtown) and inland attractions (golf, Lakewood Ranch, I-75). It's also near 2-3 east-west roads in Sarasota. Excellent. Listing is realistic, not exaggerated. It's a well-equipped kitchen with a two-burner induction stove and a large enough fridge and freezer for nearly any purpose. Good counter space and many helpful supplies and "tools" Bedroom area is large, bathroom is huge, shower is enormous, access is ez. I've stayed in tiny units and i've had faux kitchens. This is neither and with a strong host nearby. I'm tiring of long-distance hosts and corporate hosts. As a host Mariele offers proximity, professionalism, and personality too. Within reason she's on the side of the guest. Recommended listing.

This was a very cute little place with a beachy chic charm. Ed and Bunny were really welcoming and checked in via the app to make sure we had everything we needed during our stay. Ed even brought us delicious mangos from their tree! Even though the place was connected to their house it felt private and quiet. Im addition, the beautiful tropical plants and lizards scurrying along the path made it feel like a little exotic oasis in the city. We really enjoyed the stay and would love to visit again.

Great location in Sarasota! The apartment was comfortable and very clean, and just a few minutes' drive to beautiful beaches and restaurants. Vanessa and Nicole were very responsive and gave us helpful instructions. We would definitely stay here again!

Peter and Pearl are awesome hosts! The Peaceful Retreat feels welcoming and cheerful, with very comfortable furnishings. These hosts have thought of everything! The location is great too, whether you walk or drive. We were in Sarasota to attend graduation at RCAD and the location was perfect!

Great stay, responsive host, clean stay, quiet with no disturbing neighbors, lots of activities to do local.

My husband, 2 ur old twins, and I stayed at this cute little studio and it was perfect!! The place was super clean and inviting and really close to a lot of stores and restaurants. The beach isn’t a far drive at all either! We absolutely loved this stay and will definitely be back!! The hosts were so sweet and made sure to give clear instructions and check on us through out our stay!! If you’re looking for a cozy getaway that’s close to the beach and has an abundant variety of restaurants this is it!! Thank you Vanessa & Nicole!!

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.

thank you so much for allowing us the pleasure of staying in your beautiful condo. You have thought of every amenity any one could want!

We loooved it here! The space was perfect for our family. I cooked several meals and the kitchen had everything I needed. The location was convenient to grocery stores and walking distance to local restaurants and ice cream shops. The trolley stop is right at the resort so very convenient free rides to downtown Siesta Key was one of the highlights of our trip. We also grilled in the back of the resort by the bay which was nice! Oak trees all around. The pool was perfect temp. The fob didn’t work for one of the gates but there were three others we were able to get in without issue. The beds and pillows were soooo comfy. The ONLY issue we had was from the pics on the original post it appeared the walk to the closest public beach access was 2 min but it was actually 15. In the Florida heat that was rough but we pushed through! Oh and last thing, the scooters were a hit with everyone in our family. So much fun! 😆 Thank you so much for giving us an amazing stay!!

Highly recommended. Everything was clean, very quiet, and safe. Clara was very friendly, and we loved our stay.

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!!!!

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!

Exactly what we wanted. Great Location, clean and comfortable condo. Super close to the beach.