
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

Designer Home w/ Heated, Salt-Water Pool

Private Oasis W/Stunning Vinyard and Pool Views

Long Island Getaway w/ Heated Pool & Lake

Luxury Hamptons Poolside Paradise w/ Outdoor Sauna

Port Jefferson Convenient, Cozy and Chic!

Renovated Southampton Home+Pool

Summer Getaway in the Hamptons. Mins from Beaches

Extravagant Eastport Retrieve
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

Beautiful Waterview Condo on the North Fork of LI

Condo on the ocean in Montauk

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
Walk to Water. Stunning Home with Gorgeous Pool & Grounds.

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
- Jersey City Holiday rentals
- Washington Holiday rentals
- Philadelphia Holiday rentals
- Pocono Mountains Holiday rentals
- South Jersey Holiday rentals
- Jersey Shore Holiday rentals
- New York Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Plainview Holiday rentals
- The Hamptons Holiday rentals
- Boston Holiday rentals
- Rentals with breakfast Long Island
- Chalet rentals Long Island
- Cottage rentals Long Island
- Rentals with a home theatre Long Island
- Serviced apartment rentals Long Island
- Bed and breakfasts Long Island
- Waterfront rentals Long Island
- Ski-in/ski-out rentals Long Island
- Private suite rentals Long Island
- Kid-friendly rentals Long Island
- Rentals with beach access Long Island
- Pet-friendly rentals Long Island
- Rentals with an accessible height toilet Long Island
- Rentals with a sauna Long Island
- Rentals with a kayak Long Island
- Condo rentals Long Island
- Bungalow rentals Long Island
- Mansion rentals Long Island
- Guesthouse rentals Long Island
- Rentals with a washing machine and dryer Long Island
- Rentals with lake access Long Island
- Rentals with a patio Long Island
- Tiny house rentals Long Island
- Rentals with a fireplace Long Island
- Rentals with an EV charger Long Island
- Loft rentals Long Island
- Rentals with outdoor seating Long Island
- Rentals with a hot tub Long Island
- Apartment rentals Long Island
- Luxury rentals Long Island
- Boutique hotel rentals Long Island
- Smoking-friendly rentals Long Island
- Townhouse rentals Long Island
- Rentals with a fire pit Long Island
- Beach house rentals Long Island
- Farmstay rentals Long Island
- Rentals with an accessible height bed Long Island
- Hotel rentals Long Island
- House rentals Long Island
- Family-friendly rentals Long Island
- Fitness-friendly rentals Long Island
- Villa rentals Long Island
- Beachfront rentals Long Island
- Rentals with pools New York
- Rentals with pools United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- 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
- Art and culture Long Island
- Tours Long Island
- Sightseeing Long Island
- Nature and outdoors Long Island
- Sports activities Long Island
- Food and drink Long Island
- Entertainment Long Island
- Things to do New York
- Art and culture New York
- Wellness New York
- Sightseeing New York
- Entertainment New York
- Food and drink New York
- Tours New York
- Sports activities New York
- Nature and outdoors New York
- Things to do United States
- Tours United States
- Food and drink United States
- Wellness United States
- Sightseeing United States
- Art and culture United States
- Sports activities United States
- Entertainment United States
- Nature and outdoors United States