
Holiday rentals with a pool in Longboat Key
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Longboat Key
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Longboat Key rentals with a pool
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!

Sea AMI
We loved Amy’s place . Walkable to so many fun things , including the boat ramp if you do any excursions. We rented a golf cart and it was awesome and a short ride to Bean Point. The place is equipped with everything you need and more - the beach Chairs and umbrella really were nice to have. We loved the spa pool and it was so nice to dip in that after a long day at the beach. We loved AMI and hope to come back again. If your looking for a great place to- you have found it .

Wk of 6/29 now avail at last minute SALE rate!
Wonderful home in Anna Maria! Very close to the beach, pool was a nice break from the sun and many beach and pool supplies! Mark was gracious and allowed us to check in earlier as well- this was a life saver with the kids and heat! Would stay again!

༄ 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!

True Island Living House/beach/water views
This was among the most beautiful and well-appointed Airbnbs that we’ve had the pleasure of staying in! Our trip was centered around a family 60th birthday celebration and this was such a lovely backdrop for our gathering. Our primary plans were to enjoy the sunrises and gorgeous outdoor area, cooking meals on the grill and enjoying them by the pool with a view of the intercoastal waterway. As such, when we arrived to find that the grill wasn’t working properly, we were disappointed. We communicated with our host about the grill the day after our arrival, and received an immediate response. However, it ultimately required back and forth texts (some at our initiation due to not receiving an update) and three days until the handyman graciously brought over his grill to loan us. Something we learned from this trip is the importance of communicating to your hosts what it is about their place that is most important to your stay—and perhaps we should have checked on the grill specifically.

'Walk on the Beach" heated pool North End AMI
The house was walking distance to the beach, which was very nice. Rasa was very responsive.

Bayfront Gem Pool, Spa & walk to Anna Maria Beach
This was our first time to AMI , and This place was the ideal place for a family! It was central to anywhere. The kids loved the pool while my husband loved having the ability to get in the boat and go fish any time of day. The house was absolutely beautiful, master bedroom had the best view of everything and gorgeous sunrise windows to drink coffee every morning. It was hard to get me to leave. We can’t wait to come back here , Christy was beyond helpful and always very responsive when I had questions. Thank you for such a great week to unwind and enjoy our family .

Location! Beach Access + Restaurants + Trolley!
I cannot adequately put into words how perfect this air bnb was for our family. We traveled with 4 kids under 7, a teenager, 4 parents, and a grandpa. We went for a week in early June and stayed from a Saturday to Thursday. This house had everything a family might need. High chair, pack n play, baby gate, etc. I wasn’t too worried about the pool in the backyard, but the door handles were up high out of reach from the littles. And a little vacuum for all of our little messes. We walked in to a spotless paradise. You look out the big kitchen windows to see the beach! My kids were up swimming at 8 am any given morning and were happy until we made it to the beach which was just a short walk for a little family. Literally right across the road. Bridge street was a short walk as well. We enjoyed the Daquiri deck within walking distance. The grown ups enjoyed the pool after littles were in bed. The pool lights, porch lights and tv made it a vibe for all. We will be back!!!!
Apartment rentals with a pool

On the Beach; Siesta Key SunBum Studio
This wasn’t our first time at the Sun Bum … it’s the perfect get away spot. As close to the beach as you can get, has everything you need, and the hosts are BEYOND accommodating. We came for our birthday and they had a birthday banner hung on the wall waiting with a bottle of prosecco. They really make you feel special! If you’re looking for a wonderful spot for you and your spouse, this is the place!!

A&A's Paradise near IMG & Anna Maria beaches
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!!!!

Luxury 2 bedroom Beachfront Condo by FVC
Amazing place!! Loved the location, the unit and the experience!! Fantastic service with Florida Rentals!! I love forward to being a return client again! Thanks so much for making it a great trip!!

Spectacular beach to bay views from this resort.
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

Sea Side Sunsets Unit C
Great place on the beach, walking distance to restaurants. Great vibes and awesome sunsets!!

Siesta Key Beach Front Condo
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!

Beachfront - 2BR - Spectacular Beach Setting
Ryan’s place was awesome! Very easy to get to and walkable to great food and entertainment. The view of the ocean was beautiful and the walk to the beach super easy. I have never been in an Airbnb with as many towels, beach equipment and kitchen supplies. Ryan was also so very friendly and helpful. The condo was also very clean. Would stay again😊

NEW listing on AMI! Walk to fabulous beach front!
We had a great stay at Laura’s place! The beach is so close and you have a beautiful balcony lookout! It was the perfect place for our first trip with our baby
Home rentals with a private pool

New! Beautiful Pool Home Near Siesta Key Beach
It was a short stay for us, but it was exactly what we needed! The house was fully stocked with necessities. Instructions were very clear, not overwhelming. The neighborhood is nice, very close to supermarkets, shopping, restaurants, coffe shops, beach, and local areas whether you want a casual night out or a party night out! Great location😉

Comfy Home W/ Heated Pool Near Siesta Key Beach
Extremely responsive host. Even allowed us to check in early. Minimal pet fee for our two frenchies to stay. The condo has everything you need, towels, cleaning supplies, plenty of blankets and pillows. Thanks for a nice relaxing stay!

Great 6br for All Ages/heated Pool 5 Min to Beach
Place was amazing! I would give 6 stars if I could! Check in and check out were easy and host always responded very quickly to any messages! Will definitely stay here again and recommend it to anyone else! The house is also a lot bigger in person! Thanks again guys, I loved your place!

Sunny Palmetto Oasis: 4br Home with Private Pool
Thank you RedAwning Rental for the stay in Palmetto!
Quick stats about holiday rentals with a pool in Longboat Key
Total rentals
740 properties
Nightly prices starting at
$51 SGD before taxes and fees
Total number of reviews
6.9K reviews
Family-friendly rentals
600 properties are a good fit for families
Pet-friendly rentals
90 properties allow pets
Rentals with dedicated workspaces
220 properties have a dedicated workspace
Destinations to explore
- St Petersburg Holiday rentals
- Tampa Bay Holiday rentals
- Seminole Holiday rentals
- Tampa Holiday rentals
- Central Florida Holiday rentals
- Four Corners Holiday rentals
- Kissimmee Holiday rentals
- Orlando Holiday rentals
- Saint Johns River Holiday rentals
- Fort Lauderdale Holiday rentals
- Gold Coast Holiday rentals
- Miami Holiday rentals
- Rentals with a fireplace Longboat Key
- Rentals with a washing machine and dryer Longboat Key
- Beach house rentals Longboat Key
- Waterfront rentals Longboat Key
- Pet-friendly rentals Longboat Key
- Rentals with lake access Longboat Key
- Rentals with a patio Longboat Key
- Fitness-friendly rentals Longboat Key
- Flat rentals Longboat Key
- Rentals with beach access Longboat Key
- Rentals with a kayak Longboat Key
- Villa rentals Longboat Key
- Rentals with an EV charger Longboat Key
- Family-friendly rentals Longboat Key
- Townhouse rentals Longboat Key
- Family-friendly rentals Longboat Key
- Apartment rentals Longboat Key
- House rentals Longboat Key
- Rentals with a hot tub Longboat Key
- Rentals with outdoor seating Longboat Key
- Cottage rentals Longboat Key
- Rentals with a firepit Longboat Key
- Beach apartment rentals Longboat Key
- Beachfront rentals Longboat Key
- Rentals with pools Manatee County
- Rentals with pools Florida
- Rentals with pools United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Anna Maria Island
- Siesta Beach
- Anna Maria Public Beach
- Dunedin Beach
- Crescent Beach
- John's Pass
- Turtle Beach
- Caspersen Beach
- Bean Point Beach
- Raymond James Stadium
- Busch Gardens Tampa Bay
- Lido Key Beach
- Cortez Beach
- Amalie Arena
- Coquina Beach
- Gulfport Beach Recreation Area
- North Beach
- Fort De Soto Park
- Manasota Key Beach
- Vinoy Park
- Jannus Live
- Streamsong Resort
- Tampa Theatre
- ZooTampa at Lowry Park