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!
12–19 Jan
Home in Sag Harbor
4.94 out of 5 average rating, 101 reviewsSag Harbor Village Cottage with Pool
12–19 Jun
Home in Southampton
4.96 out of 5 average rating, 130 reviewsWaterview, PoolOpenNow! DogsFree+Kayaks+PingPong
12–19 Mar
Home in Patchogue
4.94 out of 5 average rating, 67 reviewsJoyful Beach House, viewing The Great South Bay
27 Dec – 3 Jan
Home in Cutchogue
4.96 out of 5 average rating, 74 reviewsSecluded Farmhouse - Studio Apartment Style Unit
29 Oct – 5 Nov
Home in Mattituck
4.98 out of 5 average rating, 41 reviewsModern farmhouse w/ pool, beach, horses and winery
22–29 Mar
Home in Hampton Bays
4.97 out of 5 average rating, 29 reviews3 bedroom house with heated, salt water pool
18–25 Apr
Home in Southold
5.0 out of 5 average rating, 10 reviewsGorgeous home with heated gunnite pool!
14–21 Apr
Apartment rentals with a pool
Apartment in Greenport
4.91 out of 5 average rating, 107 reviewsBeachside Waterview 2Br Condo w/ Pool in Greenport
8–15 Oct
Apartment in Vernon Township
4.97 out of 5 average rating, 144 reviewsComfy Studio at Mountain Creek Resort
16–23 Dec
Apartment in Montauk
4.99 out of 5 average rating, 181 reviewsMontauk Waterfront Condo w/ Sunset Views
17–24 Mar
Apartment in Montauk
4.95 out of 5 average rating, 107 reviewsDeluxe Studio Apt@The Montauk Manor
30 Mar – 6 Apr
Apartment in Greenport
4.92 out of 5 average rating, 125 reviewsBeautiful Waterview Condo on the North Fork of LI
10–17 Nov
Apartment in Vernon Township
4.95 out of 5 average rating, 238 reviewsNYC Escape 1 hr away
30 Jun – 5 Jul
Apartment in Greenport
4.83 out of 5 average rating, 145 reviewsSound front condominium
30 May – 6 Jun
Apartment in Vernon Township
4.95 out of 5 average rating, 727 reviewsAppalachian Lodge Top Floor w/views
13–20 Oct
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
21–28 Dec
Home in East Hampton
5.0 out of 5 average rating, 13 reviewsSaltbox with Separate Poolhouse in Northwest Woods
4–11 Apr
Home in Southampton
4.94 out of 5 average rating, 16 reviewsPerfect Getaway at Sunny Modern Shampton Lake House
14–21 Jan
Home in East Hampton
4.79 out of 5 average rating, 39 reviewsEnchanting Home with Large Decks and Heated Pool
2–9 Apr
Bungalow in East Hampton
4.93 out of 5 average rating, 99 reviewsEast Hampton Ranch with Access to Clearwater Private Beach
15–22 May
Home in Remsenburg
4.95 out of 5 average rating, 64 reviewsExperience a Quiet Hamptons Getaway
24–31 Jan
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
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- Yurt Rentals United States
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