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
Home in Mastic Beach
4.93 out of 5 average rating, 107 reviewsGorgeous Waterfront and Indoor Pool Family Oasis!
Home in Cold Spring
4.95 out of 5 average rating, 153 reviewsCozy, Modern Retreat in the Woods of Cold Spring
Home in Southampton
4.95 out of 5 average rating, 133 reviewsWaterview, Pool, DogsStayFree! Kayaks, PingPong
Home in Cutchogue
4.96 out of 5 average rating, 191 reviewsPrivate Oasis W/Stunning Vinyard And Pool Views
Home in Bellport
4.9 out of 5 average rating, 10 reviewsBellport Abode
Home in Cutchogue
5.0 out of 5 average rating, 26 reviewsNorth Fork paradise between beaches and vineyards
Home in Southampton
5.0 out of 5 average rating, 22 reviewsModern Southampton home, heated pool, pickleball
Home in Southampton
5.0 out of 5 average rating, 59 reviewsDream home in SH with spectacular Heated Pool
Apartment rentals with a pool
Apartment in Greenport
4.9 out of 5 average rating, 111 reviewsBeachside Waterview 2Br Condo w/ Pool in Greenport
Apartment in Greenport
4.91 out of 5 average rating, 126 reviewsBeautiful Waterview Condo on the North Fork of LI
Apartment in Montauk
4.99 out of 5 average rating, 184 reviewsMontauk Waterfront Condo w/ Sunset Views
Apartment in Vernon Township
4.97 out of 5 average rating, 147 reviewsComfy Studio at Mountain Creek Resort
Apartment in Montauk
4.95 out of 5 average rating, 111 reviewsDeluxe Studio Apt@The Montauk Manor
Apartment in Vernon Township
4.95 out of 5 average rating, 738 reviewsAppalachian Lodge Top Floor w/views
Apartment in Vernon Township
4.97 out of 5 average rating, 220 reviewsRustic Chic at Mountain Creek! Pool Open All Year!
Apartment in Greenport
4.83 out of 5 average rating, 150 reviewsSound front condominium
Home rentals with a private pool
Home in East Hampton
4.97 out of 5 average rating, 116 reviewsExplore the Water & Woods at a Relaxing Retreat
Home in East Hampton
4.77 out of 5 average rating, 13 reviewsHistorical Estate Home with Backyard Pool
Home in East Hampton
5.0 out of 5 average rating, 13 reviewsSaltbox with Separate Poolhouse in Northwest Woods
Home in East Hampton
4.8 out of 5 average rating, 41 reviewsEnchanting Home with Large Decks and Heated Pool
Home in Southampton
4.94 out of 5 average rating, 16 reviewsPerfect Getaway at Sunny Modern Shampton Lake House
Destinations to explore
- New City Holiday rentals
- Newark Holiday rentals
- Montauk Holiday rentals
- Hoboken Holiday rentals
- New Haven Holiday rentals
- Jersey Shore Holiday rentals
- Washington Holiday rentals
- Philadelphia Holiday rentals
- Jersey City Holiday rentals
- New York Holiday rentals
- The Hamptons Holiday rentals
- Boston Holiday rentals
- Rentals with pools New York
- Rentals with pools United States
- Rentals with pools Manhattan
- Rentals with pools Brooklyn
- Bungalow rentals Long Island
- Rentals with a firepit Long Island
- Private suite rentals Long Island
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- Rentals with an accessible-height bed Long Island
- Serviced apartment rentals Long Island
- Rentals with a fireplace Long Island
- Bed and breakfasts Long Island
- Rentals with a kayak Long Island
- Villa rentals Long Island
- Wheelchair-accessible rentals Long Island
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- Rentals with a sauna Long Island
- Rentals with an EV charger Long Island
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- Cabin rentals Long Island
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- Rentals with beach access Long Island
- Rentals with a cinema Long Island
- Mansion rentals Long Island
- Guest house rentals Long Island
- Ski-in/ski-out rentals Long Island
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- Rentals with a hot tub Long Island
- Smoking-friendly rentals Long Island
- Townhouse rentals Long Island
- Rentals with breakfast Long Island
- Rentals with lake access Long Island
- Family-friendly rentals Long Island
- Hotel rentals Long Island
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- Rentals with a patio Long Island
- Rentals with a washing machine and dryer Long Island
- Rentals with an accessible-height toilet Long Island
- Boutique hotel rentals Long Island
- Holiday home rentals Long Island
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- Farm stay rentals Long Island
- Apartment rentals Long Island
- House rentals Long Island
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- Tiny house rentals Long Island
- Flat rentals Long Island
- Rentals with pools New York
- 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
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- 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
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- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
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- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom