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.

Guest favorite

Home in Shelter Island

4.97 out of 5 average rating, 189 reviews

Huge 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

$920 per night
Guest favorite

Guest suite in Redding

4.89 out of 5 average rating, 102 reviews

Artist 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

$161 per night
Guest favorite

Cottage in Guilford

4.96 out of 5 average rating, 157 reviews

Luxury 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

$293 per night

Popular amenities for Long Island rentals with a pool

House rentals with a pool

Guest favorite

Home in Cheshire

5.0 out of 5 average rating, 116 reviews

Pool House

Nov 1 – 8

$126 per night
Guest favorite

Home in Cutchogue

4.96 out of 5 average rating, 189 reviews

Stunning Vinyard Views - Spring Special $475/Nt!

Dec 23 – 30

$719 per night
Guest favorite

Home in Southampton

4.96 out of 5 average rating, 129 reviews

Waterview, PoolOpenNow! DogsFree+Kayaks+PingPong

Mar 15 – 22

$314 per night
Guest favorite

Home in Cold Spring

4.95 out of 5 average rating, 152 reviews

Cozy, Modern Retreat in the Woods of Cold Spring

Jan 17 – 24

$480 per night
Guest favorite

Home in Patchogue

4.94 out of 5 average rating, 64 reviews

Joyful Beach House, viewing The Great South Bay

Oct 28 – Nov 4

$149 per night
Guest favorite

Home in Cutchogue

4.96 out of 5 average rating, 72 reviews

Secluded Farmhouse - Studio Apartment Style Unit

Dec 23 – 30

$280 per night
Guest favorite

Home in Hampton Bays

4.97 out of 5 average rating, 29 reviews

3 bedroom house with heated, salt water pool

Mar 2 – 9

$350 per night
Guest favorite

Home in Mattituck

4.97 out of 5 average rating, 36 reviews

Modern farmhouse w/ pool, beach, horses and winery

Jan 28 – Feb 4

$379 per night
Guest favorite

Home in Sag Harbor

4.84 out of 5 average rating, 45 reviews

Modern Home in Sag Harbor, NY

May 16 – 23

$681 per night
Guest favorite

Home in Southampton

5.0 out of 5 average rating, 37 reviews

Bay View Stunner, Modern 6 Bedroom w Heated Pool

May 16 – 23

$557 per night
Superhost

Home in Fire Island

4.87 out of 5 average rating, 23 reviews

Beachside Oasis w/ Pool • Views • Rooftop • Atrium

Apr 10 – 17

$792 per night
Guest favorite

Home in Southampton

5.0 out of 5 average rating, 32 reviews

Luxury Hamptons Poolside Paradise w/ Outdoor Sauna

Nov 9 – 16

$638 per night

Condo rentals with a pool

Guest favorite

Condo in Greenport

4.91 out of 5 average rating, 107 reviews

Beachside Waterview 2Br Condo w/ Pool in Greenport

Oct 10 – 17

$267 per night
Guest favorite

Condo in Vernon Township

4.97 out of 5 average rating, 210 reviews

Rustic Chic at Mountain Creek! Pool/Hot Tub/Sauna

Mar 7 – 14

$120 per night
Guest favorite

Condo in Montauk

4.99 out of 5 average rating, 177 reviews

Montauk Waterfront Condo w/ Sunset Views

Sep 4 – 11

$471 per night
Guest favorite

Condo in Greenport

4.93 out of 5 average rating, 122 reviews

Beautiful Waterview Condo on the North Fork of LI

Jul 20 – 27

$693 per night
Guest favorite

Condo in Vernon Township

4.97 out of 5 average rating, 141 reviews

Comfy Studio at Mountain Creek Resort

Oct 28 – Nov 4

$90 per night
Guest favorite

Condo in Greenport

4.83 out of 5 average rating, 141 reviews

Sound front condominium

Jun 3 – 10

$501 per night
Guest favorite

Condo in Montauk

4.95 out of 5 average rating, 106 reviews

Deluxe Studio Apt@The Montauk Manor

Aug 24 – 31

$421 per night
Guest favorite

Condo in Vernon Township

4.94 out of 5 average rating, 235 reviews

NYC Escape 1 hr away

$157 per night
Guest favorite

Condo in Montauk

4.8 out of 5 average rating, 228 reviews

Montauk Royal Atlantic Beach Resort North

Aug 7 – 14

$450 per night
Guest favorite

Condo in Vernon Township

4.95 out of 5 average rating, 722 reviews

Appalachian Lodge Top Floor w/views

Aug 22 – 29

$150 per night
Guest favorite

Condo in Vernon Township

4.9 out of 5 average rating, 298 reviews

Appalachian TOP 4TH FLOOR Studio+ w/amazing views!

Mar 1 – 8

$136 per night
Guest favorite

Condo in Vernon Township

4.9 out of 5 average rating, 196 reviews

Upscale Condo Ski-In/Out Mountain Creek 1 hr NYC

Apr 11 – 18

$150 per night

Destinations to explore