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Holiday rentals with a pool in Longboat Key

Find and book unique homes with a pool on Airbnb

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Popular amenities for Longboat Key rentals with a pool

House rentals with a pool

Guest favourite
Home in Anna Maria
4.9 out of 5 average rating, 59 reviews

Island in the Sun, luxury beach house,private pool

JamieRating, 5 stars2 months ago
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!
Guest favourite
Home in Holmes Beach
4.96 out of 5 average rating, 182 reviews

Sea AMI

JessicaRating, 5 stars2 weeks ago
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 .
Top guest favourite
Home in Holmes Beach
5 out of 5 average rating, 36 reviews

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

ChristiRating, 5 stars1 week ago
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!
Top guest favourite
Home in Anna Maria
5 out of 5 average rating, 38 reviews

༄ Sunset Shore on Anna Maria Island ༄

AshleyRating, 5 stars1 week ago
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!
Guest favourite
Home in Sarasota
4.96 out of 5 average rating, 71 reviews

True Island Living House/beach/water views

CourtneyRating, 5 stars1 month ago
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.
Top guest favourite
Home in Anna Maria
5 out of 5 average rating, 27 reviews

'Walk on the Beach" heated pool North End AMI

KathrynRating, 5 stars3 days ago
The house was walking distance to the beach, which was very nice. Rasa was very responsive.
Guest favourite
Home in Holmes Beach
4.93 out of 5 average rating, 60 reviews

Bayfront Gem Pool, Spa & walk to Anna Maria Beach

LoreeRating, 5 stars4 days ago
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 .
Top guest favourite
Home in Bradenton Beach
5 out of 5 average rating, 62 reviews

Location! Beach Access + Restaurants + Trolley!

WhitneyRating, 5 stars2 weeks ago
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

Top guest favourite
Apartment in Siesta Key
4.97 out of 5 average rating, 320 reviews

On the Beach; Siesta Key SunBum Studio

AlexRating, 5 stars1 day ago
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!!
Top guest favourite
Apartment in Bradenton
4.96 out of 5 average rating, 102 reviews

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

AmyRating, 5 stars4 weeks ago
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!!!!
Guest favourite
Apartment in Longboat Key
5 out of 5 average rating, 5 reviews

Luxury 2 bedroom Beachfront Condo by FVC

JenniferRating, 5 stars1 month ago
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!!
Top guest favourite
Apartment in Treasure Island
4.99 out of 5 average rating, 188 reviews

Spectacular beach to bay views from this resort.

LaraRating, 5 stars2 weeks ago
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
Guest favourite
Apartment in Indian Rocks Beach
5 out of 5 average rating, 9 reviews

Sea Side Sunsets Unit C

AngelaRating, 5 stars1 month ago
Great place on the beach, walking distance to restaurants. Great vibes and awesome sunsets!!
Guest favourite
Apartment in Siesta Key
4.94 out of 5 average rating, 109 reviews

Siesta Key Beach Front Condo

JenniferRating, 5 stars2 weeks ago
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!
Guest favourite
Apartment in Sarasota
5 out of 5 average rating, 27 reviews

Beachfront - 2BR - Spectacular Beach Setting

ChristineRating, 5 stars2 weeks ago
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😊
Top guest favourite
Apartment in Holmes Beach
4.98 out of 5 average rating, 125 reviews

NEW listing on AMI! Walk to fabulous beach front!

EmilyRating, 5 stars2 weeks ago
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

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

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