Vacation 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.
Vacation rentals for every style
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Popular amenities for Long Island rentals with a pool
House rentals with a pool
Home in Cold Spring
4.95 out of 5 average rating, 152 reviewsCozy, Modern Retreat in the Woods of Cold Spring
Oct 19 – 26
Home in Sag Harbor
4.85 out of 5 average rating, 250 reviewsExclusive Sag Harbor Compound
Oct 28 – Nov 4
Home in Southampton
4.87 out of 5 average rating, 237 reviewsSecluded Southampton Luxury Estate with tennis 288
Oct 27 – Nov 3
Home in Mattituck
4.98 out of 5 average rating, 40 reviewsModern farmhouse w/ pool, beach, horses and winery
Feb 14 – 21
Home in Cutchogue
4.96 out of 5 average rating, 74 reviewsSecluded Farmhouse - Studio Apartment Style Unit
Oct 18 – 25
Home in Southold
5.0 out of 5 average rating, 10 reviewsGorgeous home with heated gunnite pool!
Feb 23 – Mar 2
Home in Hampton Bays
4.97 out of 5 average rating, 29 reviews3 bedroom house with heated, salt water pool
Jan 16 – 23
Home in Southampton
5.0 out of 5 average rating, 34 reviewsLuxury Hamptons Poolside Paradise w/ Outdoor Sauna
Feb 13 – 20
Condo rentals with a pool
Condo in Greenport
4.91 out of 5 average rating, 107 reviewsBeachside Waterview 2Br Condo w/ Pool in Greenport
Oct 8 – 15
Condo in Vernon Township
4.97 out of 5 average rating, 144 reviewsComfy Studio at Mountain Creek Resort
Jan 27 – Feb 3
Condo in Montauk
4.99 out of 5 average rating, 181 reviewsMontauk Waterfront Condo w/ Sunset Views
Feb 27 – Mar 6
Condo in Montauk
4.95 out of 5 average rating, 107 reviewsDeluxe Studio Apt@The Montauk Manor
Apr 12 – 19
Condo in Greenport
4.93 out of 5 average rating, 124 reviewsBeautiful Waterview Condo on the North Fork of LI
Nov 29 – Dec 6
Condo in Vernon Township
4.97 out of 5 average rating, 215 reviewsRustic Chic at Mountain Creek! Pool|Hot Tub|Sauna!
Apr 12 – 19
Condo in Vernon Township
4.95 out of 5 average rating, 727 reviewsAppalachian Lodge Top Floor w/views
Oct 14 – 21
Condo in Greenport
4.83 out of 5 average rating, 144 reviewsSound front condominium
Jul 23 – 30
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
Dec 18 – 25
Home in East Hampton
4.79 out of 5 average rating, 39 reviewsEnchanting Home with Large Decks and Heated Pool
Sep 25 – Oct 2
Home in Southampton
4.94 out of 5 average rating, 16 reviewsPerfect Getaway at Sunny Modern Shampton Lake House
Jan 11 – 18
Home in East Hampton
5.0 out of 5 average rating, 13 reviewsSaltbox with Separate Poolhouse in Northwest Woods
Apr 1 – 8
Bungalow in East Hampton
4.93 out of 5 average rating, 99 reviewsEast Hampton Ranch with Access to Clearwater Private Beach
May 31 – Jun 7
Home in Remsenburg
4.95 out of 5 average rating, 64 reviewsExperience a Quiet Hamptons Getaway
Jan 21 – 28
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