Holiday 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

Guest favourite
Home in Indian Beach-Sapphire Shores
4.98 out of 5 average rating, 87 reviews

Retreat by the Bay-Heated Saltwater Pool

AdriannaRating, 5 stars3 weeks ago
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!
Top guest favourite
Home in Bradenton Beach
5 out of 5 average rating, 19 reviews

Sunset View

AngelaRating, 5 stars1 week ago
We had a blast! The house was everything we expected and Renee was very responsive! Zero complaints! 10/10
Guest favourite
Home in Bradenton Beach
4.96 out of 5 average rating, 105 reviews

Canal-Front Retreat w/ Pool, Dock & Beach Access

BrianRating, 5 stars1 month ago
This place was great! Would stay here again. Easy walking distance to the beach. Would recommend this place to anyone.
Top guest favourite
Home in Anna Maria
5 out of 5 average rating, 69 reviews

Bean Pt. Bungalow - Half duplex w/private pool

ScottRating, 5 stars6 days ago
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.
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.
Top guest favourite
Home in North Port
4.97 out of 5 average rating, 134 reviews

Cozy & Beautiful Pool Villa in Sarasota County, FL

AnthonyRating, 5 starstoday
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!
Top guest favourite
Home in Bradenton Beach
4.97 out of 5 average rating, 170 reviews

STEPs to BEACH! /Heated Salt Pool/Sunsets/5 STAR!

JoeRating, 5 stars2 weeks ago
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!
Guest favourite
Home in Anna Maria
4.96 out of 5 average rating, 73 reviews

Beach House w/Private Pool & Hot Tub by Bean Point

NaomiRating, 5 stars3 weeks ago
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

Superhost
Apartment in Sunset Beach
4.92 out of 5 average rating, 48 reviews

INCREDIBLE SUNSET BEACH OCEANFRONT TOP FLOOR CONDO

MaryRating, 5 stars1 month ago
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.
Top guest favourite
Apartment in Sarasota
5 out of 5 average rating, 46 reviews

Breathtaking Beachfront Views in Siesta Key

AverieRating, 5 stars2 weeks ago
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!
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 stars1 week 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 Siesta Key
4.94 out of 5 average rating, 107 reviews

Siesta Key Beach Front Condo

JessicaRating, 5 stars1 month ago
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!
Guest favourite
Apartment in St. Pete Beach
4.93 out of 5 average rating, 123 reviews

1145 Sqft! - 2 Bedroom 2 Bath (GULF FACING!) Condo

JessicaRating, 5 stars2 weeks ago
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!
Top guest favourite
Apartment in Tampa
4.95 out of 5 average rating, 302 reviews

Modern Waterfront Condo - Captivating Sunset Views

KateRating, 5 stars1 week ago
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.
Guest favourite
Apartment in Lido Key
4.91 out of 5 average rating, 79 reviews

Lido-Key- Tiny, Yet Charming Studio-B

PaytonRating, 5 stars1 month ago
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!
Top guest favourite
Apartment in Bradenton
4.98 out of 5 average rating, 206 reviews

Shorewalk full condo IMG Beaches Anna Maria

FrankRating, 5 stars3 days ago
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!

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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