
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

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!

Breezy Harbor AMI pool retreat near the Beach
Great location. Everything was a short drive, and the beach was a short walk. The place was very clean and stocked. My family had everything we needed during our vacation. We had a great time and would return.

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

Anna Margaritas by Beach Boutique Rentals
Absolutely would stay here again! The backyard pool was a perfect set up for peace and relaxation with beautiful beaches only being a walk away. The hosts were amazing as we navigated evacuation for hurricane Helena. My friends and I will definitely be staying here again. They had everything you needed for a beach vacation!

༄ Sunset Shore on Anna Maria Island ༄
10 of us stayed at Jeff and Ingrid’s and it was perfect! The house was beautiful, plenty of linens and kitchen necessities. The location was great for walking to shops or beach! Loved the outdoor area! Perfect to unwind after the beach or dinner. We will be back!

White Sands Villa - Heated Pool/Spa - Near Beaches
We had a great stay at this property. Seaglass Management was always responsive and accommodating. The house was clean and the backyard was large and well maintained. The only downside was the bathroom situation. There is no master bathroom and one of the bathrooms for the house is really a 3/4 bath. For 8 adults and a baby the bathroom situation was a little difficult, but we made it work.

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!!

Casa Bonita
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!
Weekly house rentals

Luxury 3/3 with Heated Pool, Spa, & Putting Green!
Erinn was an amazing host - she would respond immediately to any text and was always friendly and helpful. The house is as good as it looks if not better! My husband complains about every airbnb I book but he even he had to admit this one was top notch.

Just 5 miles to Anna Maria Island Beaches + IMG!
We had an amazing stay! We had a family of 8 and the house was perfect for all of us. The house was absolutely beautiful! It was super clean. We spent a lot of time in the pool and hot tub. The outdoor table also has a fire pit which was perfect at night. There were lots of amenities provided. There’s plenty of beach supplies/ extra towels. The house was filled with lots of stuff we didn’t have to pack, because it was already there. The beach is super close, about 10 minutes away, which was a bonus. Ashley has been wonderful! She’s super responsive and even allowed us to check in an hour early. We have a great vacation! We couldn’t recommend this place more! The perfect family vacation home.

NEW saltwater pool/spa! Amazing outdoor space!
House was very clean and spacious. The outdoor space was great, and the house has lots of amenities that came in handy

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!

Tranquility on the bay.
Bettina has a lovely home and it’s close to all beaches. The neighborhood is peaceful and quiet! Very relaxing. Bettina is proactive, friendly and very responsive. She made check in and check out very easy and is always asking for help. I can see why she’s a super host! I would recommend for a peaceful getaway close to the beaches.

Oceanfront Home with Heated Pool in Fishers Haven
House is immaculate! Super clean and comfortable. Beds and linens were luxurious! Ceiling fans in entry room including the screened in porch. Nice touch! Backyard waterfront is amazing. We used pool and hot tub multiple times per day. We fished off the dock and caught a few catfish. Sergiy was a perfect host. Excellent communication and direction when needed. Highly recommend!

L'Oasis West w/Dip Pool
I absolutely loved this peaceful, pristine and beautiful vacation home on Anna Maria Island. It is centrally located amongst turquoise beaches, delicious local food, fun gift shops and fully stocked grocery stores. The home itself was very clean, well maintained and beautifully decorated, both inside and outside. The living room was comfy, and had a lovely view of the front yard. The kitchen was the perfect size and the refrigerator was huge! The master bedroom was cozy and the bed very comfortable. The bathroom was very clean and the shower quite large. I also loved that there was a washer and dryer attached to the master bedroom. The outside was just as gorgeous as the inside. The palm trees, and numerous plants really added to the whole oasis feel, and added a layer of seclusion and privacy. I loved the fact that there was an outdoor shower and the dip pool was such a great bonus! The hosts checked in regularly and were very responsive. I would absolutely recommend this home!

Tiki Bar Paradise! Heated Pool & Gaming Oasis!
All of us were so happy with this place! The location was so perfect. The house was amazing and had everything we needed. We could’ve hung out there all day and had a great time. We want to come back and spend more time at the house!!! Great stay, highly recommend!
Private house rentals

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!

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.

Heated Pool |Game Room|SmartTVs|King Beds|Sleeps14
We had a wonderful stay at this beautiful home. This home is super clean, well styled, and spacious. The backyard oasis is amazing - very private and quiet. The location is great; the home is close to all amenities as well as the beach. Communication with the host was exceptional. Dana is super responsive and very friendly and accommodating. I highly recommend booking this home!

"Lost Loon" Oceanfront Cottage by Roxy Rentals
If I could give this home 10 stars, I would! This is the only Airbnb we’ve ever returned to, and we’re already planning our next stay for our family of four. The home instantly feels welcoming: fresh flowers, snacks on the counter, even a fridge stocked with cold drinks.. little touches that make you feel like you’re visiting a friend’s house and not a rental. Janine is a wonderfully responsive and thoughtful host. The home is spotless, cozy, and stocked with all the things you might forget to pack (sunblock, toiletries, even slippers). The towels are plush and plentiful, there are extra linens and blankets, and the beds are incredibly comfortable; we slept so well after our days at the beach! Most importantly, you truly can’t beat having a beautiful, quiet beach right in your own backyard. This house is a gem.

Perfect Hideaway- Post Storms Better Than Ever!
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.

Canal front, dock, heated Pool, near AMI+IMG
Absolutely pristine place, the house is amazing, location is perfect and loaded with everything you need. Great host as well , we would love to come back to this place.

Cozy Cottage - close to Manatee River
This cottage was cozy and beautiful. It had everything you needed and more. It was in a nice, quiet neighborhood & a close drive to the beach. We loved having access to the beach gear & the backyard had everything you could dream of. The hosts were friendly and helpful.

The Mango House Beach Cottage
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.
Quick stats about house rentals in Longboat Key
Total rentals
220 properties
Nightly prices starting at
$39 SGD 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
- Siesta Beach
- Anna Maria Public Beach
- Dunedin Beach
- Crescent Beach
- John's Pass
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- Caspersen Beach
- Bean Point Beach
- Raymond James Stadium
- Busch Gardens Tampa Bay
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- Amalie Arena
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- Gulfport Beach Recreation Area
- North Beach
- Fort De Soto Park
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- Vinoy Park
- Jannus Live
- Streamsong Resort
- Tampa Theatre
- ZooTampa at Lowry Park