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Beach house holiday rentals in Longboat Key

Find and book unique beach houses on Airbnb

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Popular amenities for Longboat Key beach house rentals

Beachfront house rentals

Top guest favourite
Home in Sarasota
4.97 out of 5 average rating, 68 reviews

Your DreamOasisAwaits: SiestaKeyEscape with Pool!

GabriellaRating, 5 stars1 week ago
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.
Top guest favourite
Home in Holmes Beach
5 out of 5 average rating, 35 reviews

Wk of 6/29 now avail at last minute SALE rate!

TinaRating, 5 stars1 week ago
The listing says it is just a few steps from the beach and that is true! It was so easy to go back and forth and with 4 kids and beach items that was very important. The house was beautiful and spotless. We felt right at home and we loved every second of our stay! Thanks Mark for helping us make a special family vacation!
Guest favourite
Home in Longboat Key
4.89 out of 5 average rating, 9 reviews

Beautiful Island Beach House

LoriRating, 5 stars9 months ago
My family had a wonderful vacation at Danielle 's house. It was everything and more than we expected. The house is beautifuly appointed with all you would need to thoroughly enjoy your stay. The kitchen is loaded with everything you could ever want to cook any meal. It is spacious & inviting for the family to gather together while we cooked. The house itself is majestic. The great room when you 1st walk in is so incredible. The house is inviting and makes you feel right at home. The beds are incredibly comfortable, bathrooms are big & roomy and the showers... oh my, full body shower heads make taking a shower a luxury. The lenai with the pool and hot tub is the perfect gathering place and oh so nice to take a swim after a long day at the beach. The dock out back is perfect for a morning coffee or evening beverage. We rented a kayak for the week & had a blast paddling out to the sound. The beach is private & so nice to enjoy the day at. Thank you Danielle for our great memories.
Guest favourite
Home in Siesta Key
5 out of 5 average rating, 8 reviews

Toes In The Sand | Private Pool, Walk to Beach!

AmyRating, 5 stars2 weeks ago
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!
Top guest favourite
Home in Holmes Beach
5 out of 5 average rating, 45 reviews

Perfect Hideaway- Post Storms Better Than Ever!

PixyRating, 5 stars2 weeks ago
Rebecca’s place was perfect for our family vacation of two young children, two parents and two grandparents. Her house sits on a dead end street just a few blocks from the beach. We found everything we needed for a few meals at home, and having a washer and dryer was convenient. The kicker was the outdoor pool, which we loved. We would easily recommend her place to anyone who wants a beautiful place to spend vacation.
Top guest favourite
Home in Lido Key
5 out of 5 average rating, 24 reviews

Walk to Lido Beach &St. Armands -grill/HEATED POOL

AnnieRating, 5 stars1 week ago
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!
Superhost
Home in Bradenton Beach
5 out of 5 average rating, 4 reviews

Casa Bonita

SonyaRating, 5 stars1 week ago
Our stay at Casa Bonita was truly a five star experience. The location was great, just steps from the beach access crossing and bridge street where we enjoyed, shops, dining and drinks. No ubers needed! The actual space itself exceeded our expectations. There is plenty of space for lounging inside and out. The pool area offered shading and full sun areas, with games and a bathroom/shower located outside for easy rinsing off. The garage had everything we needed for the perfect beach trip including towels, floats and a wagon. Kitchen and bedrooms were very clean with all of the essentials. And our host Kelly was very responsive with anything we needed. We will certainly be back to Casa Bonita!
Guest favourite
Home in Holmes Beach
5 out of 5 average rating, 15 reviews

One Level Large Home 2 Minute Walk to the Beach!

JoannaRating, 5 stars1 month ago
From the minute you get there the grounds are beautifully kept, crisp and lush. Inside was immaculate and the fenced, private backyard with pool did not disappoint. Tropical landscape, a variety of comfy options for relaxing or dining and the pool was perfect! We paid extra to have it heated and it was totally worth it…especially for my young children(3 and 7) to swim and not shiver:-). This place has a nice light, airy, relaxed, indoor outdoor vibe! My parents traveled with us as well and also loved it! The very short walk to the beach was perfect and opened up to this beautiful, seemingly private beach. You could see the public beach down a bit where there were quite a few umbrellas, but no one around where we were. Very nice! The neighborhood was beautiful and quiet as well. Communicating with the host was very easy and she always responded. We had a great vacation and will definitely be back.

Beach house rentals with a pool

Top guest favourite
Home in Anna Maria
5 out of 5 average rating, 36 reviews

Veselka - Canal front w private heated pool & dock

CarrieRating, 5 stars1 week ago
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!
Top guest favourite
Home in Bradenton
5 out of 5 average rating, 9 reviews

100 yr Old Stone Home by Beaches

EmilyRating, 5 stars1 day ago
Their rental was our favorite so far! very clean and comfy. We felt very comfortable and enjoyed grilling out by the pool. Location was great. we enjoyed our nightly walks in their neighborhood on the water. Plan to come back!
Top guest favourite
Home in Bradenton
5 out of 5 average rating, 69 reviews

NEW saltwater pool/spa! Amazing outdoor space!

KobeRating, 5 stars4 days ago
House was very clean and spacious. The outdoor space was great, and the house has lots of amenities that came in handy
Guest favourite
Home in Bradenton
4.93 out of 5 average rating, 145 reviews

2.5mi 2 beach+Pets OK+Pvt Pool+Grill+Tropical Yard

AdrianaRating, 5 stars1 week ago
We had an amazing time at 200 Palms! The home is exactly as pictured with spacious bedrooms and living areas stocked with many comforts that make you feel at home. The backyard truly felt like an oasis with room to swim, grill, and play as a family. We traveled with our three children, who spent countless hours in the pool when we weren't exploring AMI. We really appreciated having pool toys and beach equipment in the shed because it made for easy beach excursions and saved us time from shopping for additional gear. If you have kids, they will love the lofted bedroom and the outdoor tree house area. The location of the home is extremely convenient as there is a grocery store less than two miles away, excursions in Bradenton are close, and getting to AMI is a breeze. The backyard makes you feel like you have a private space to enjoy. Brian is extremely responsive and all communication was prompt and clear. Overall, we would absolutely stay here again!
Guest favourite
Home in Venice
4.95 out of 5 average rating, 106 reviews

Spacious 2 Bedroom Home | Near Beach | Heated Pool

BilliRating, 5 stars1 week ago
Beautiful home in Venice! Perfect for families, the kids loved the pool. The house was clean, and organized. We loved the location and felt safe. Would definitely stay again. If you stay here make the drive to Sarasota & eat at WALTS! We went 3x! The best seafood around 🐡🐟🐠
Top guest favourite
Home in Anna Maria
5 out of 5 average rating, 11 reviews

Becker's Beach Bungalow by A Shore Thing Vacations

BernabeRating, 5 stars1 week ago
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.
Guest favourite
Home in Anna Maria
5 out of 5 average rating, 14 reviews

Our Great Escape by Duncan Real Estate

John And LizRating, 5 stars2 months ago
We had an amazing stay at Duncan's home. Everything was perfect. The only thing that was a slight issue was that the elevator wasn't working, but it wasn't really a big deal for us. We just weren't told before we checked in and it would've been nice to know in case we did have somebody that was unable to use the stairs since the elevator is the only access from the entry level besides the stairs but it was because of the recent hurricane so there was nothing they could really do about it otherwise, everything was perfect!
Top guest favourite
Home in Holmes Beach
4.97 out of 5 average rating, 30 reviews

Loggerhead - AMI Oasis w/ Private Pool + Golf Cart

AmandaRating, 5 stars6 days ago
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!!

Private beach house rentals

Guest favourite
Home in Siesta Key
4.77 out of 5 average rating, 512 reviews

Beachfront Getaway in Siesta Key

AdairRating, 5 stars2 weeks ago
Our stay was so easy and enjoyable! Dior’s place is so cute and very clean. We were able to walk to multiple shops, bars, and restaurants. It was so nice to have our private beach access right down the sidewalk, and right beside the pool! We were also so glad that she was able to accommodate us on such short notice. Everything was perfect! This will definitely be our go-to place to stay when we visit Siesta!
Top guest favourite
Home in Indian Beach-Sapphire Shores
5 out of 5 average rating, 83 reviews

Magical Secluded Retreat

KellyRating, 5 stars1 month ago
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.
Guest favourite
Home in Sarasota
4.96 out of 5 average rating, 46 reviews

New! 3 Bed/3 Bath Pool Home Oasis! Great Location

AnnaRating, 5 stars1 week ago
⭐️⭐️⭐️⭐️⭐️ 5/5 – A Perfect Getaway! We had an incredible stay at Mario’s villa in Sarasota! The home was spotless, beautifully decorated, and had everything we needed for a relaxing and comfortable trip. The pool was absolutely amazing—clean, private, and perfect for soaking up the Florida sun. The location was great too—close to the beach, restaurants, and local markets. Mario was an outstanding host—responsive, friendly, and genuinely thoughtful. He made sure we felt welcomed and had everything we needed from start to finish. You can tell he truly cares about his guests having a great experience. Highly recommend staying here if you’re visiting Sarasota. We’re already looking forward to coming back. Thank you, Mario!
Guest favourite
Home in Downtown Sarasota
5 out of 5 average rating, 20 reviews

Historic Downtown Sarasota - Gem I

JackieRating, 5 stars2 weeks ago
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.
Guest favourite
Home in Indian Beach-Sapphire Shores
4.93 out of 5 average rating, 71 reviews

The Happy House - Seeing is Believing!

EmilyRating, 5 stars1 week ago
We had an amazing time at Happy Home. The pool and screened in patio were highlights for our family. The backyard was a little oasis. We appreciated how organized the house was with labels on lighting, kitchen draws, and cabinets. The binder with house reminders and local recommendations was helpful. The kitchen is well stocked with spices and pots, pans, dishes. The dedicated office space was helpful since my husband was working remotely. I also loved all the original artwork and beautiful lighting. Happy Home is walking distance to a few local restaurants and a super cute cafe/used book store, Shelf Indulgence. The little beach in the bay is a super close walk and made going to watch the sunset and see boats easy and relaxing. We would definitely recommend and would stay again.
Guest favourite
Home in Sarasota
4.92 out of 5 average rating, 75 reviews

Downtown Sarasota | Casa de Zara

LeeAnnRating, 5 stars4 days ago
Fantastic. Five stars. Lots of space both inside and outside. Quality house, wonderful furnishings and details. Comfortable beds with nice sheets. Nice art- no home goods prints. Faith was extremely responsive. Neighborhood was quiet and the place felt safe and secure. They thought of all the details that makes a short term rental a pleasant experience. Could not have been more pleased. Highly recommend.
Guest favourite
Home in Holmes Beach
5 out of 5 average rating, 6 reviews

Rollin' wth the Waves by Beach Boutique Rentals

StephanieRating, 5 stars1 month ago
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!
Top guest favourite
Home in Sarasota
5 out of 5 average rating, 89 reviews

The Mango House Beach Cottage

SavannahRating, 5 stars1 day ago
Had an amazing time staying at the mango! It was the perfect private spot about 10 minutes from the beach that couldn’t have been any better for my husband and I. We did have a slight AC problem during the middle of the week but Whitney responded so quickly and was able to get it fixed so fast while we enjoyed our day at the beach.

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