
House holiday rentals in Longboat Key
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Top-rated house rentals in Longboat Key
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Popular amenities for house rentals in Longboat Key
House rentals with a pool

Wk of 6/29 now avail at last minute SALE rate!
We had an absolutely fantastic time. The home was delightful. The ease of getting to and from the beach plus all the beach chairs and amenities Mark provided for the beach really made it all so easy. Our kids loved the pool and the set up. Beds were very comfortable. Everything was easy to find. Thank you so much for letting us enjoy your home!!!

Waterfall | Spa | Saltwater Pool | Private Oasis B
The house is located in a great location! The beach is not a far drive and there is plenty to do in the area! The house is also beautiful and the backyard with the pool and hot tub are amazing !

HeatPool~Pickleball~Mini-Golf~4 Kings+Kids Suite!
Excellent place, thank you Patrick for your help anytime!!! I recommend it

La Hacienda / heated pool, hot tub, 6 mi to beach
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.

Becker's Beach Bungalow by A Shore Thing Vacations
Excellent accommodations super close to the beach and many places to eat. The home felt like a second home with all needs met. The backyard was an oasis and the pool was delightful! The host was quick to respond and I would highly recommend.

Discount 33% June 3-Day and July 4-Day w/Dock-Pool
My family and I absolutely loved our experience!! The hosts were attentive and quick to respond with clear instructions. House was cleaned and amply stocked with everything you need for a family of five. The pool was amazing and we definitely saved some money by having a fully functioning kitchen and grill for dinner and lunch. Very close to the beach. Two scoops ice cream is amazing with quick service as it is very busy and the general store was only a quick drive to get anything else we needed or forgot to pack. Bean Point beach is where you want to be if you don’t like overcrowded beaches, however, parking is limited so I recommend getting there early!! Also recommend renting a golf cart for extended stays and if you have kids like I did. Plenty of options around the island. I would recommend 100% and we definitely will be back!!

Walk to Lido Beach &St. Armands -grill/HEATED POOL
Book this immediately! This house is a beautiful, peaceful, tropical oasis that is close to the beach and restaurants. After a day at the beach, the private pool is a great escape. Claudia was very responsive and kind, she answered any questions we had. We were provided with a great starter pack of house items so we could start relaxing right away!

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

Your DreamOasisAwaits: SiestaKeyEscape with Pool!
This Airbnb exceeded every expectation! The property was beautiful, spotless, and incredibly well-maintained. The pool was a highlight—clean, peaceful, and the perfect spot to relax every day. The host was friendly, responsive, and made sure we had everything we needed for a comfortable stay.

Luxury 3/3 with Heated Pool, Spa, & Putting Green!
My wife and I had a great time at this stay. Lots to do at the house along with great beaches and restaurants within a 15-20 minute drive. The house was clean and had everything that you might need. We were able to drive to Disney in just over an hour and a half which provided a different experience to go along with the daily beach/pool trips. Cool AC inside to combat the humid 88 degree weather in June 2025.

Island in the Sun, luxury beach house,private pool
Had the absolute best stay here! Everything was perfect, from the interior design to the location. The pool was great with lots of privacy in the backyard. The house was spacious, each bedroom having a king and its own bathroom. My son loved that. We would love to stay here again!

Coastal Retreat near Siesta Key Beach and Downtown
We had the most perfect stay at Aubrey’s! We loved everything about it! Great location, so comfortable and nice, close to great restaurants and close to beach as well. The design features of the house and everything in it is very well curated and a house you want to spend time in and enjoy the beauty. The beach chairs and umbrella were perfect for the beach. We highly recommend Aubrey’s place and will definitely stay here when we come back! Melissa and John

Boutique Rental Near AMI Beaches+IMG • Renovated
This was one of our favorite stays!! Such a beautiful home, clean and cozy. The hosts are so friendly and responsive! Close by to so many amazing beaches and restaurants and fun things to do. Thank you so much for an amazing stay!

Loggerhead - AMI Oasis w/ Private Pool + Golf Cart
Ross and Hannah’s place was great for our family if 5! The pool with tv set up was amazing for our kiddos many movies in the pool during the week made it so much fun! We also loved the convenience of using the golf cart, was so close to shops and restaurants (we only used our rental car once to go to Cortez)! Hannah was also very quick to respond and s gracious host. We would recommend to families coming to ami- a good value!!

Chasing the Sun Lido Beach House
Excellent location. great beach down the street. Everything was exactly as expected. thank you

Cozy Cottage - close to Manatee River
Cute Airbnb ! Very well decorated and super cozy. Easy drive to Anna Maria Island
Private house rentals

100 yr Old Stone Home by Beaches
Beautiful home! The interior is stunning and beautifully decorated. The pool is AMAZING! Super close to the beach and lots of food near. 10/10!

Veselka - Canal front w private heated pool & dock
We had an amazing week at Michael and Denzel’s home! It was actually better than the pictures with enough space for everyone to feel right at home. The layout was perfect for two families. The home is spotless and extremely well stocked. The island is beautiful and we enjoyed the pool everyday! Highly recommend this home. It will exceed your expectations in every way!

Toes In The Sand | Private Pool, Walk to Beach!
The rental was very clean and had everything we needed. Kitchen was well equipped and the grill was a plus! Our toddler loved the pool and all the beach toys! We enjoyed the location and quick access to the beach and restaurants. Will definitely consider staying again!

Magical Secluded Retreat
This was, by far, my best experience at an Airbnb in all the years I’ve used the app! The house is beautiful— spacious yet cozy and filled with so many thoughtful details. You will want for nothing here: books, games, bug spray, citronella candles, towels (including wash cloths!), shampoo and body lotion for all skin and hair types, portable lights and speakers for outdoor use, and a smart TV on a cart which can be rolled anywhere in the house! I didn’t watch TV much, as I spent most of my free time in the luscious front yard enjoying bird watching and staring at the trees. The house is located a short distance to a lot of things, including a sweet little park/lake nearby. Nancy is a kind and generous host, respectful of privacy but also happy to chat, connect and make sure you have everything you need. I’m sad to leave this place, if there hadn’t been another reservation afterwards, I most certainly would have extended my stay! This is a wonderful, safe, and deeply restorative home.

Historic Downtown Sarasota - Gem I
Adorable. Cutest little house on the block. Location was perfect and walkable to everything. Quiet and safe while still being downtown. Check in was easy and parking right next to the home was so nice.

Great House / Great Location ~ with Heat Pool~
we just spent a week at Ryan's place and it was amazing! the space was very clean and organized. this was one of the better equipped airbnb homes I have stayed in. the kitchen was well organized and had many convenient items most places do not have. there were beach chairs, sand toys, and even a wagon, which with having three kids was a blessing. the pool was amazing and maintained the temp of 88. I know some previous reviews discussed jet noise, as this is super close to SRQ but the jet noise was not an issue for us, and there were maybe 10 flights a day that we heard. Ryan was great at responding and providing instructions that were essential for our stay. we had a great time and my kids had the best time and are already asking when we can be back.

Downtown Oasis: Poolside Condo, Patio & Gym
Stayed here for the national rowing competition for one week. The place is lovely - very clean, the complex is nice & the pool is great. It was a perfect location for us - halfway between the race course where we needed to be every day and close to downtown. The beach wasn’t far either and I liked the location and the complex very much. We felt safe and it was pretty quiet and peaceful. The owner is responsive and detail oriented with how to check in, get into the unit, etc. I would stay here again.

Rollin' wth the Waves by Beach Boutique Rentals
Perfect location 3 houses away from a beautiful, powder white sand, tranquil beach with lots of seashells. You do not have to cross a busy street to get to the beach which was important for our family with 3 littles. The backyard/pool area was amazing. At all times of the day there were both sunny spots, for those that like to tan, and shady spots for those that prefer to stay cool. The pool/spa was perfect for our family of 5 (2 adult, 3 kids). The pool is a little on the small side so it probably would be too cramped with any more people, or bigger kids. There is a nice outdoor shower to rinse off sandy feet/toys from the beach. We spent most of our time at the beach, in the pool, and grilling. The inside of the house was very clean and had everything as described in the listing. Publix & Dollar Tree are 5 mins drive away so we were about to get everything we needed there. We went out to eat a few times, loved The Porch restaurant, highly recommend! Would love to return!
Quick stats about house rentals in Longboat Key
Total rentals
220 properties
Nightly prices starting at
₹2,596 before taxes and fees
Total number of reviews
3.9K reviews
Family-friendly rentals
190 properties are a good fit for families
Pet-friendly rentals
90 properties allow pets
Rentals with a pool
140 properties have a pool
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- Anna Maria Island
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