
Holiday rentals with a pool in Long Island
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Long Island
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 Long Island rentals with a pool
House rentals with a pool

North Fork paradise between beaches and vineyards

Private Oasis W/Stunning Vinyard and Pool Views

Spectacular Southampton Retreat!

Luxury Hamptons Poolside Paradise w/ Outdoor Sauna

Curated Artist Home with New Pool

Coastal Retreat|Heated Saltwater Pool|5 MinToBeach

Monkey Puzzle - Renovated Cottage in Bellport

Summer Getaway in the Hamptons. Mins from Beaches
Condo rentals with a pool

1 BR Loft Apt- Montauk Manor- Pools, Tennis & Gym!

Seaside Summer Escape: 2BR Waterfront Condo w/Pool

Montauk Waterfront Condo w/ Sunset Views

Waterfront Elevated Bungalow - Spectacular Views

Beautiful Waterview Condo on the North Fork of LI

1856 Trading House close to water

Beachside Waterview 2Br Condo w/ Pool in Greenport

Deluxe Studio Apt@The Montauk Manor
Home rentals with a private pool

Explore the Water & Woods at a Relaxing Retreat
East Hampton Ranch with Access to Clearwater Private Beach
Enchanting Home with Large Decks and Heated Pool
Perfect Getaway at Sunny Modern Shampton Lake House
Saltbox with Separate Poolhouse in Northwest Woods
Destinations to explore
- Plainview Holiday rentals
- East River Holiday rentals
- The Hamptons Holiday rentals
- New York Holiday rentals
- Jersey Shore Holiday rentals
- Hudson Valley Holiday rentals
- South Jersey Holiday rentals
- Philadelphia Holiday rentals
- Pocono Mountains Holiday rentals
- Boston Holiday rentals
- Ocean City Holiday rentals
- Washington Holiday rentals
- Rentals with an accessible height bed Long Island
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- Times Square
- Beach
- Bryant Park
- Madison Square Garden
- Grand Central Terminal
- Empire State Building
- Columbia University
- Barclays Center
- Jones Beach
- Fairfield Beach
- Yale University
- Southampton Beach
- MetLife Stadium
- Citi Field
- Rye Beach
- Yankee Stadium
- Gilgo Beach
- United Nations Headquarters
- Central Park Zoo
- USTA Billie Jean King National Tennis Center
- Statue of Liberty
- Cooper's Beach, Southampton
- Rockefeller Center
- Radio City Music Hall
- Things to do Long Island
- Sports activities Long Island
- Nature and outdoors Long Island
- Food and drink Long Island
- Entertainment Long Island
- Tours Long Island
- Art and culture Long Island
- Sightseeing Long Island
- Things to do New York
- Art and culture New York
- Nature and outdoors New York
- Wellness New York
- Sports activities New York
- Entertainment New York
- Sightseeing New York
- Food and drink New York
- Tours New York
- Things to do United States
- Tours United States
- Food and drink United States
- Art and culture United States
- Entertainment United States
- Sightseeing United States
- Nature and outdoors United States
- Wellness United States
- Sports activities United States