Holiday rentals with outdoor seating in Longboat Key

I came down with 2 friends for a moms getaway and we had a wonderful time. This sweet little house is perfect and we will definitely be back. Amy is so nice and accommodating. The house was very clean and convenient to everything we wanted to do. Can’t wait to visit again.

When I saw this new listing, I hesitated—no reviews and almost too-perfect photos. But the owners quickly answered my questions, were responsive, and I’m so glad we booked. The home is exactly as pictured: spotless, spacious, beautifully designed. The pool area is a dream—plenty of space for our group of 11 (with 4 kids), with waterfall features, a sauna, and even a sandy play area. The movie room and golf simulator were a hit too! Beds are comfy, rooms are big and inviting, Wi-Fi is great. Peaceful, safe neighborhood with tons of privacy. Carter and Naomi were responsive and kind to any concerns we had, and took care of everything. Amazing hosts. This home is a gem.

We had a great time. Super clean, beautiful home, full of extras. The property has many things to do and keep everyone entertained. Great communication, definitely one of our favorite vacation homes. Can’t wait to stay here again!!!

What a beautiful place. My kids and I felt like we were home and safe with surrounding area. Bettina was a gem with updates and check in’s. Just an awesome vacation for us. Can’t wait to go back!

This place is worth more than what we paid. Having the docks for fishing and the beach a block away made this place exquisite. The beach was practically empty every day, which is what we loved. Our stay was clean and comfortable. We recommend staying with Cole!

Beautiful home and surrounding area, Pristine home in brand new condition. Expertly furnished, lots to do for teenagers, they loved the ice bath! Well stocked kitchen. The host was very responsive and helpful would definitely recommend this location and home. Happy vacationing.

We had a blast! The house was everything we expected and Renee was very responsive! Zero complaints! 10/10

had a great stay! just as pictured! Location was perfect - 2 mins to the beach and restaurants!

Confession: I almost don’t want to write this review because I want this place to stay my little pre-cruise hideaway. But here we are. This Airbnb was absolutely adorable—I walked in and immediately wanted to hire the host to redecorate my entire life. Every detail was spot on: cozy but modern, clean as a whistle, and so well thought out. It made the night before our cruise feel like a vacation all on its own. If you’re debating, just book it (but maybe leave it open for when I want to come back, thanks!).

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.

Cozy guest home, with all the right amenities you need when visiting Florida. Great location near downtown Bradenton as well!

Thank you so much! It was exactly what we needed for 2 days. Wish we could’ve stayed longer.

JUST BOOK! That’s really all you need to know. If you’re thinking about booking—stop thinking and just book it. This place was everything. Nicole and her team left no stone unturned. From the moment I arrived, I felt like I had stepped into a curated sanctuary built for rest, ease, and deep healing. The beach is literally steps away, but truthfully, I barely needed to leave the property. The pool is warm and inviting, the lounge areas are serene, and the attention to detail throughout the space is unmatched. Every comfort you can imagine is thoughtfully provided—from beach wagons and umbrellas to luxurious towels and a perfectly appointed kitchen. This wasn't just a stay; it was a spiritual reset. Whether you're coming for clarity, connection, or just a beautiful break, trust me—this is the place. Thank you, Nicole, for creating a space where peace lives. I’ll be back.

My daughter and I only stayed here for 1 night but found plenty within walking distance. There are restaurants, shops, and a 7-11 across the street. The pool and beach are a short walk around the block and down the street. The sunset on the beach was beautiful. Justin was very responsive and accommodating, as I had difficulty understanding the map and needed written instructions to the pool/beach area:)

We had a wonderful stay at Mike and Wendy’s! The location is amazing, the private dock is a nice perk that we utilized every day for fishing, and the unit itself is very clean, stylish, and well maintained. We would recommend to our family/friends and would definitely stay here again!

cute little beach apartment. clean and comfortable. We loved being super close to the beach. and the outdoor hose and shower was handy. nice of them to provide some beach items too like chairs, a boogie board and beach towels. AC gets very cold, which my husband was happy about. We will definitely be back to Ana Maria Island! its an amazing beach.

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!

Excellent location! Everything you need is in the condo. Hope to come back soon!

Loved the location and the layout of the condominium! We will be coming back!

My daughter and I stayed for a mother daughter girls trip and had a blast! They made sure to take care of every little detail to make you feel comfortable and at home. Even checking in and making sure we made it ok. It was very clean and the location was amazing. Easy to get around on the trolly if we didn't want to drive and literally steps away from the beautiful white sand and clear turquoise beach. Do yourself a favor and book the trip!

Scott’s place was very nice for a weekend. The location is perfect. The accès to the beach was fast. Scott’s place was very clean and looks exactly like the pictures . Very responsive for any questions or help. Recommended

Our stay was great! The place and location were perfect! We had absolutely everything we needed. Communication was awesome! Thanks so much!! Lara and Thomas Boulder Co

We enjoyed our stay at the Island Inn. The staff was very friendly and the host was quick to respond to our questions. We liked the view from the room and that we were right on the beach. It was helpful having beach chairs and umbrellas to use so we didn't have to pay for them everyday. I think it was great for 2 adult guests, any more than that and the space might start feeling a little cramped. We used the grills outside to cook as well as the hot plates so we were able to make whatever we wanted. Great view of the sunset from the building, we watched the sun go down from the balcony and beach, very peaceful at night. Overall a great stay!

We had a lovely stay at 42 Gulf Blvd IRB! The house is comfortable, the beach area is peaceful and beautiful, and the location is perfect for a relaxing getaway. While we did experience a couple of issues during our stay, we truly appreciate how responsive and caring the management team was. They took our concerns seriously and handled the situation with professionalism and kindness. Their communication made all the difference. We would absolutely stay here again and highly recommend it to others looking for a laid-back and enjoyable beach experience!