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

Retreat by the Bay-Heated Saltwater Pool
Will's place was amazing! Super clean, comfortable, and exactly as described. The location was perfect - there was so much to do nearby, from the beach, great restaurants and shops. Will was also a fantastic host: responsive and helpful. Highly recommend staying here if you're looking for a spot that's both relaxing and close to all the action!

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

Canal-Front Retreat w/ Pool, Dock & Beach Access
This place was great! Would stay here again. Easy walking distance to the beach. Would recommend this place to anyone.

Bean Pt. Bungalow - Half duplex w/private pool
I’ve stayed at a lot of places and Joey’s place was the best of the best. Joey is a great host who takes care of his guests. The home was clean and well maintained. It was comfortable and cozy. It had everything we needed. I can’t say enough about how relaxing the space was. It was a very low stress experience and I would happily visit again.

One Level Large Home 2 Minute Walk to the Beach!
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.

Cozy & Beautiful Pool Villa in Sarasota County, FL
I stayed at Vera’s house for a week and had an amazing experience from start to finish. The place was exactly as described—clean, spacious, and well-equipped with everything I needed for a comfortable stay. The neighborhood was peaceful and safe, with easy access to shops and local attractions. The host was incredibly responsive and helpful, making check-in and check-out smooth and stress-free. I especially appreciated the thoughtful touches around the home. Highly recommend this host to anyone looking for a relaxing and hassle-free stay. I’d definitely book again!

STEPs to BEACH! /Heated Salt Pool/Sunsets/5 STAR!
We had a great stay! The home was perfect and beach access was perfect! We very much appreciated having all of the beach necessities available, beach chairs and beach carts to get them there. We will definitely be staying here in the future!

Beach House w/Private Pool & Hot Tub by Bean Point
This was a beautiful trip with our family. Ammey was astonishingly attentive to our needs and was quick to provide guidance. We are thankful for the time we had.
Apartment rentals with a pool

INCREDIBLE SUNSET BEACH OCEANFRONT TOP FLOOR CONDO
Beautiful view of the Gulf of America to watch dolphins, shipping carriers and cruise ships coming and going. The beach area is mostly crushed shells until you get to the water. Nice seeing the beach was patrolled by police regularly even in a gated area. Was able to see Manatee in the canal and watch fishing boats coming and going. Parking was easy. Condo is very clean and well decorated with that comfortable relaxing feeling - we enjoyed the balcony for awesome sunsets and star gazing or our morning coffee. The restaurant/bars are not within walking distance but were only a short drive (all of them had good food). You pay by card for parking at most locations. We would definitely stay at this beautiful location again - one of my most relaxing trips.

Breathtaking Beachfront Views in Siesta Key
this was by far our favorite vacation ever! the place was very clean, cozy, and perfect for our week. the hosts were very kind and responsive. can’t recommend this enough! siesta key was a beautiful place to stay, as well. so many good restaurants and little shops with lots to do! our favorite restaurant was spearfish 10/10 recommend. we will definitely be coming back again to this airbnb!

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

Siesta Key Beach Front Condo
Our stay was exactly what we wanted. Our host, Evan, was great and quick with any questions we had. The condo was located very close to Siesta Key Beach, and we didn't have to drive more than 20 minutes to get to anything that we wanted to around that area, some things even within walking distance. Everything we could have possibly wanted was provided in our home, which really made the week stress-free. We would definitely stay here again!

1145 Sqft! - 2 Bedroom 2 Bath (GULF FACING!) Condo
This condo was hands down one of the best places I’ve ever stayed! It was clean, spacious, and beautiful. Best of all, the view of the ocean was absolutely amazing. We enjoyed sunsets over the ocean right from our balcony every night. We are thrilled to have found this gem by our favorite beach spot and plan to return each time we visit St. Pete!

Modern Waterfront Condo - Captivating Sunset Views
Rosana was an excellent host- very responsive, kind, and accommodating. Fun location on the bay with a great view, pool with towel service, and bar/grill with great burgers. Fire pit on the little beach at night with great view of sunset. The unit is in a quiet location within the complex with a view of the beach and bay. The trade-off is that the unit is a bit far from the elevator (though close to stairs). Great experience overall.

Lido-Key- Tiny, Yet Charming Studio-B
Once again we had an amazing stay in lido! This year we visited for the week as a mini honeymoon, and it was perfect! We love visiting the area and this bnb is perfect for the two of us! We look forward to coming back next year. We enjoyed walking St. Armand’s and nice dinners in longboat!

Shorewalk full condo IMG Beaches Anna Maria
I've stayed in Shorewalk 4 different times now, but you're place has been the best, by far. Super clean and accommodating. Great communication and always quick to respond. Thank you!
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😉

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!

Comfy Home W/ Heated Pool Near Siesta Key Beach
Quick stats about holiday rentals with a pool in Longboat Key
Total rentals
740 properties
Nightly prices starting at
₹3,462 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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- 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
- Cortez Beach
- Lido Key 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