
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

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

Beautiful heated pool home, minutes from beaches

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

Poolside Bliss in Clearwater! Heated-pool/Spa

Spacious House w/ Pool & Hot Tub near Tampa

Beautiful House with Heated pool

Beautiful, Spacious Heated Pool Home

Spacious Heated Pool Home Near Siesta Key
Apartment rentals with a pool

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

POOL SIDE right on the BEACH 2 bdrm condo

*Waterfront *2 Bedroom Condo *Amazing Sunsets*Pool

Tiki Themed Waterfront Condo on Tampa Bay

Lovely 2 bedrooms condo with pool in Boca Ciega

SUNNY DELIGHT! HEATED POOL 2 miles to the beach🐶

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

5 *Waterfront Condo,3 Beds,2 Baths, Pool, HOT-TUB.
Quick stats about holiday rentals with a pool in Longboat Key
Total rentals
730 properties
Nightly prices starting at
€ 37 before taxes and fees
Total number of reviews
6.6K reviews
Family-friendly rentals
580 properties are a good fit for families
Pet-friendly rentals
80 properties allow pets
Rentals with dedicated workspaces
220 properties have a dedicated workspace
Destinations to explore
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- Crescent Beach
- John's Pass
- Cortez Beach
- Bean Point Beach
- Lido Key Beach
- Busch Gardens Tampa Bay
- Amalie Arena
- North Beach
- Raymond James Stadium
- Clearwater Beach
- Vinoy Park
- Coquina Beach
- Curtis Hixon Waterfront Park
- Tampa Theatre
- Fort De Soto Park
- Tropicana Field
- Manasota Key Beach
- ZooTampa at Lowry Park
- Splash Harbour Water Park
- Lakewood National Golf Club
- Streamsong Resort
- River Strand Golf and Country Club
- Sand Key Beach
- Honeymoon Island State Park