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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 Tampa
4.89 out of 5 average rating, 149 reviews

Pool Oasis | Karaoke | 5G | Theater 135" | Grill

NiaghaRating, 5 stars1 week ago
Everything was just like the listing stated. Easy access to everything and plenty to do in the house itself. Its funny but they have notes posted around the house with different instructions or just to let you what light switches you are using. Only problem I had, I couldnt beat PAC MAN!!!!!! WOULD definitely recommend!!
Guest favourite
Home in Largo
5 out of 5 average rating, 5 reviews

Oasis in Largo. Beautiful pool house, hot tub.

PeggyRating, 5 stars1 week ago
We loved staying at Nga’s place. Sophia who we had to contact with any issues was amazing. We ran into a few problems in the beginning but she was quick to respond and take care of it. The pool was very nice. The canal really behind the house was my husband’s favorite place to relax. A lot of wildlife which he really enjoyed. The neighborhood was quiet and neighbors were very friendly. I loved the screen in porch with a tv. We definitely would stay again if we came back in this area. I can’t say enough about how great Sophia was. You can’t go wrong renting this place.
Superhost
Home in Venice
4.56 out of 5 average rating, 16 reviews

Lovely pool house 5 minutes from the beach

LindaRating, 5 stars12 months ago
Had a lovely stay here. Communication with Carmen was fantastic. Decorating in home was tasteful and lovely and we felt right at home.
Superhost
Home in Tampa
4.83 out of 5 average rating, 78 reviews

Dream Villa

DavidRating, 5 stars2 weeks ago
Lovely accommodations. Pool was fantastic. Quiet surroundings. Screened in patio and very spacious. We lucked out with beautiful weather.
Guest favourite
Home in Largo
4.81 out of 5 average rating, 80 reviews

Tranquil Home. 2 minutes to Indian Rock Beach...

TerrenceRating, 5 stars4 weeks ago
Gisele's place was clean and just like the pictures showed. The pool area was nice with a large Weber grill and lots of chairs . There were plenty of pool rafts in the garage for our use. Grocery stores, liquor stores, and restaurants all within a short drive and some within walking distance. The neighborhood was friendly and quiet and had a Catholic church within a 2 minute walk. We would definitely consider staying again!
Guest favourite
Home in Clearwater
4.88 out of 5 average rating, 173 reviews

Poolside Bliss in Clearwater! Heated-pool/Spa

CarmenRating, 5 stars3 weeks ago
This was a great place for me and my family. She was very kind ! Definitely would stay here again …..
Superhost
Home in Brandon
4.92 out of 5 average rating, 12 reviews

Spacious House w/ Pool & Hot Tub near Tampa

AmandaRating, 5 stars3 weeks ago
Enjoyed our stay, we used the pool and hot tub. It worked out great. Plenty of space to hang out and enjoy yourself when you’re not out doing. All the dishes and pans were easily found to cook at the house, that was excellent for us
Guest favourite
Home in Sarasota
4.93 out of 5 average rating, 30 reviews

Beautiful, Spacious Heated Pool Home

KristenRating, 5 stars3 days ago
We booked with Alice last minute after our previous rental didn’t work out and we are so glad because this home was perfect! Immaculate, great kitchen, pool was great, master shower was amazing! Lots of fluffy beach towels, nice assortment of beach toys and floats for the pool, fold up bag chairs, cooler, large washer and dryer… it had everything our small family needed and more. We will be back!

Condo rentals with a pool

Guest favourite
Condo in Bradenton
5 out of 5 average rating, 10 reviews

Lovely Condo, Heated Pools, AMI, IMG, Top beaches

Luis AlbertoRating, 5 stars2 weeks ago
Perfect service, very friendly, comfortable and well-located area
Superhost
Condo in Indian Shores
4.9 out of 5 average rating, 20 reviews

POOL SIDE right on the BEACH 2 bdrm condo

CaseyRating, 5 stars3 months ago
This condo was perfect for our family vacation! We had everything we could have needed and our host made everything so easy.
Guest favourite
Condo in Tampa
4.92 out of 5 average rating, 78 reviews

*Waterfront *2 Bedroom Condo *Amazing Sunsets*Pool

KatrenaRating, 5 stars3 weeks ago
Our family had a wonderful time at this condo! We enjoyed waking to see the ocean every day and also had enough space to relax on our vacation. Helena provides a beach bag with towels and sand toys that were a very nice touch for our beach day. The staff at the bar/restaurant were great and we also felt safe with the 24 hour security guards on duty. This place really made our trip extra special!
Top Guest favourite
Condo in Tampa
4.97 out of 5 average rating, 148 reviews

Tiki Themed Waterfront Condo on Tampa Bay

PatriceRating, 5 stars1 day ago
Chris was very helpful and proactive through messages and short videos. Made everything easy. Would definitely stay again.
Guest favourite
Condo in St. Petersburg
4.91 out of 5 average rating, 23 reviews

Lovely 2 bedrooms condo with pool in Boca Ciega

JohnRating, 5 stars9 months ago
Matt was the best at explaining everything and. Was so quick. To respond and answer and questions I had as well as give me great info around the area. Would rent from him again for sure and recommend him to anyone looking for a great place and helpful with any questions you might have.
Top Guest favourite
Condo in Seminole
4.97 out of 5 average rating, 145 reviews

SUNNY DELIGHT! HEATED POOL 2 miles to the beach🐶

DonaRating, 5 stars1 month ago
Sandra's Place was EVERYTHING thats in the posting. She has everything there for you in case u missed something while packing. The place feels like its urs, furnished well, felt like home. Thanks Sandra
Guest favourite
Condo in Sarasota
4.97 out of 5 average rating, 63 reviews

Peaceful retreat, pool, hot tub, near Siesta Key!

DavidRating, 5 stars1 week ago
Suzanne was very responsive, the residence was clean, spacious and well equipped. Will definitely stay again.
Guest favourite
Condo in Clearwater
4.94 out of 5 average rating, 116 reviews

POOL VIEW IN A MODERN CONDO - Feel at Home

SusanRating, 5 stars3 months ago
The condo was great. Impeccably clean and provided everything you might need during your stay. It was excellent value for the rate. It was also a very short and simple drive to get to Clearwater beach. I would definitely go back.

Quick stats about holiday rentals with a pool in Longboat Key

  • Total rentals

    740 properties

  • Nightly prices starting at

    $63 AUD 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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