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.
Home in Shelter Island
4.97 out of 5 average rating, 189 reviewsHuge Island Getaway Pool HotTub Walk To Beach
Relaxation begins on the 6 minute ferry ride to this magical island. Summerfield is a spectacular, grand compound that has it all. Huge main house great for groups, 4700ft w/ privacy for all overlooking serene nature reserve. Star gaze in the bubbling hot tub, grill outside after a swim, play in the rec room with movie theater, pool table or ping pong,or watch TV by the fire! Open plan layout, gourmet kitchen, heated gunite pool, separate guest house. Prime location close to beach + restaurants.
Dec 1 – 8
Guest suite in Redding
4.89 out of 5 average rating, 102 reviewsArtist Retreat in Beautiful Country Setting
Stay at this unique property, owned and designed by a Eu artist, and enjoy the quiet countryside and natural beauty that rural CT has to offer. A large one bedroom studio with an modern fireplace, is equipped with a comfortable king size bed, full bathroom, sauna, indoor resistance pool- available at an extra charge, kitchen, a dedicated workspace, and high-speed internet for seamless remote work. Relax in the evening at your own private outdoor seating area surrounded by the property's charm.
Sep 16 – 23
Cottage in Guilford
4.96 out of 5 average rating, 157 reviewsLuxury cottage by the sea with hot tub and pool
We built this guest cottage to provide an ultimate luxury experience for people wanting to escape from hectic life!With incredible coastal views, this home is a haven of tranquility. It sits on a special stretch of the Connecticut coast, with spectacular bird and wild life-watching year-round. Enjoy great shopping in Guilford's boutiques around the historic town green. Watch the sun set over the water and relax in the hottub for some night time star gazing year round (pool open June-beg/mid Oct)
Feb 11 – 18
Vacation 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 Cheshire
5.0 out of 5 average rating, 116 reviewsPool House
Nov 1 – 8
Home in Cutchogue
4.96 out of 5 average rating, 189 reviewsStunning Vinyard Views - Spring Special $475/Nt!
Dec 23 – 30
Home in Southampton
4.96 out of 5 average rating, 129 reviewsWaterview, PoolOpenNow! DogsFree+Kayaks+PingPong
Mar 15 – 22
Home in Cold Spring
4.95 out of 5 average rating, 152 reviewsCozy, Modern Retreat in the Woods of Cold Spring
Jan 17 – 24
Home in Patchogue
4.94 out of 5 average rating, 64 reviewsJoyful Beach House, viewing The Great South Bay
Oct 28 – Nov 4
Home in Cutchogue
4.96 out of 5 average rating, 72 reviewsSecluded Farmhouse - Studio Apartment Style Unit
Dec 23 – 30
Home in Hampton Bays
4.97 out of 5 average rating, 29 reviews3 bedroom house with heated, salt water pool
Mar 2 – 9
Home in Mattituck
4.97 out of 5 average rating, 36 reviewsModern farmhouse w/ pool, beach, horses and winery
Jan 28 – Feb 4
Home in Sag Harbor
4.84 out of 5 average rating, 45 reviewsModern Home in Sag Harbor, NY
May 16 – 23
Home in Southampton
5.0 out of 5 average rating, 37 reviewsBay View Stunner, Modern 6 Bedroom w Heated Pool
May 16 – 23
Home in Fire Island
4.87 out of 5 average rating, 23 reviewsBeachside Oasis w/ Pool • Views • Rooftop • Atrium
Apr 10 – 17
Home in Southampton
5.0 out of 5 average rating, 32 reviewsLuxury Hamptons Poolside Paradise w/ Outdoor Sauna
Nov 9 – 16
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 10 – 17
Condo in Vernon Township
4.97 out of 5 average rating, 210 reviewsRustic Chic at Mountain Creek! Pool/Hot Tub/Sauna
Mar 7 – 14
Condo in Montauk
4.99 out of 5 average rating, 177 reviewsMontauk Waterfront Condo w/ Sunset Views
Sep 4 – 11
Condo in Greenport
4.93 out of 5 average rating, 122 reviewsBeautiful Waterview Condo on the North Fork of LI
Jul 20 – 27
Condo in Vernon Township
4.97 out of 5 average rating, 141 reviewsComfy Studio at Mountain Creek Resort
Oct 28 – Nov 4
Condo in Greenport
4.83 out of 5 average rating, 141 reviewsSound front condominium
Jun 3 – 10
Condo in Montauk
4.95 out of 5 average rating, 106 reviewsDeluxe Studio Apt@The Montauk Manor
Aug 24 – 31
Condo in Vernon Township
4.94 out of 5 average rating, 235 reviewsNYC Escape 1 hr away
Condo in Montauk
4.8 out of 5 average rating, 228 reviewsMontauk Royal Atlantic Beach Resort North
Aug 7 – 14
Condo in Vernon Township
4.95 out of 5 average rating, 722 reviewsAppalachian Lodge Top Floor w/views
Aug 22 – 29
Condo in Vernon Township
4.9 out of 5 average rating, 298 reviewsAppalachian TOP 4TH FLOOR Studio+ w/amazing views!
Mar 1 – 8
Condo in Vernon Township
4.9 out of 5 average rating, 196 reviewsUpscale Condo Ski-In/Out Mountain Creek 1 hr NYC
Apr 11 – 18
Home rentals with a private pool
Home in Water Mill
4.91 out of 5 average rating, 109 reviewsBeach Barn w/ Sauna and Heated Pool - Dog Friendly
Nov 19 – 26
Home in East Hampton
4.97 out of 5 average rating, 115 reviewsExplore the Water & Woods at a Relaxing Retreat
Nov 24 – Dec 1
Home in East Hampton
4.94 out of 5 average rating, 16 reviewsWalk to Water. Stunning Home with Gorgeous Pool & Grounds.
May 5 – 12
Home in Southampton
4.94 out of 5 average rating, 16 reviewsPerfect Getaway at Sunny Modern Shampton Lake House
Oct 11 – 18
Home in East Hampton
5.0 out of 5 average rating, 13 reviewsSaltbox with Separate Poolhouse in Northwest Woods
Mar 5 – 12
Home in East Hampton
4.79 out of 5 average rating, 39 reviewsEnchanting Home with Large Decks and Heated Pool
Apr 12 – 19
Bungalow in East Hampton
4.93 out of 5 average rating, 99 reviewsEast Hampton Ranch with Access to Clearwater Private Beach
Apr 20 – 27
Home in Remsenburg
4.95 out of 5 average rating, 64 reviewsExperience a Quiet Hamptons Getaway
Sep 30 – Oct 7
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