Vacation rentals with a pool in The Hamptons

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in The Hamptons

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.

Jan 27 – Feb 3

$994 per night
Guest favorite

Condo in Montauk

4.99 out of 5 average rating, 177 reviews

Montauk Waterfront Condo w/ Sunset Views

Modern 1 Bedroom Condo in gated community (Rough Riders) with sunset views from beautiful deck. The community has multiple tennis courts, pool, jacuzzi, and sauna (pool area only open Late May - early October). The property is great for walks along the boardwalk and many guests enjoy fishing and swimming off the pier. The unit is less than a 5 minute car / Uber ride to town and a short 5-10 minute walk to Navy Beach and Duryea's. Strong wifi in unit, Smart TV ( Netflix, etc, - no cable)

Sep 21 – 28

$397 per night
Guest favorite

Cottage in Southampton

4.96 out of 5 average rating, 162 reviews

Secluded Southampton Cottage w/Pool & Spa

*Follow Us on Insta @SimmerCottage* This designer-decorated cozy cottage near Southampton Village & a short drive or bike to the beach has a stocked chef's kitchen, cozy living room with wood-burning stone fireplace, 2 SmartTVs, whimsical dining room, 3 bedrooms, one bath & charming sunroom w/reading nooks. The Cottage has central heating/air & is set on a gated 1/2 acre w/hot-tub, outdoor dining for 8 on a stone patio, outdoor string lights, fire pit, gardener's potting station & gas BBQ.

Apr 12 – 19

$315 per night

Popular amenities for The Hamptons rentals with a pool

House rentals with a pool

Guest favorite

Home in East Hampton

4.92 out of 5 average rating, 125 reviews

Kid-friendly, heated pool, games room, near beach

Sep 13 – 20

$900 per night
Guest favorite

Home in Southampton

5.0 out of 5 average rating, 32 reviews

Luxury Hamptons Poolside Paradise w/ Outdoor Sauna

Mar 13 – 20

$638 per night
Guest favorite

Home in East Hampton

4.96 out of 5 average rating, 55 reviews

East Hampton Family Vacation Home

Feb 24 – Mar 3

$500 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
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 Sag Harbor

4.98 out of 5 average rating, 85 reviews

Designer in Sag Harbor 5 Br 1 block from water

Mar 20 – 27

$549 per night
Guest favorite

Home in East Hampton

5.0 out of 5 average rating, 57 reviews

Serene East Hampton Escape - Pool Open 4/19

May 6 – 13

$591 per night
Guest favorite

Home in East Hampton

4.93 out of 5 average rating, 14 reviews

Cozy Beach Oasis in East Hampton + Pool

Sep 15 – 22

$750 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

Dec 31 – Jan 7

$350 per night
Guest favorite

Home in East Hampton

4.9 out of 5 average rating, 29 reviews

Newly Renovated Hamptons Home with Heated Pool

May 12 – 19

$685 per night
Guest favorite

Home in East Hampton

5.0 out of 5 average rating, 22 reviews

Book your summer Getaway(Heated Pool+Peloton Bike)

Jan 17 – 24

$475 per night
Superhost

Home in East Hampton

4.96 out of 5 average rating, 24 reviews

Bright Modern Home With Stunning Yard & Pool

Jan 31 – Feb 7

$599 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

May 12 – 19

$205 per night
Guest favorite

Condo in Montauk

4.95 out of 5 average rating, 106 reviews

Deluxe Studio Apt@The Montauk Manor

Aug 23 – 30

$421 per night
Guest favorite

Condo in Montauk

4.8 out of 5 average rating, 228 reviews

Montauk Royal Atlantic Beach Resort North

Aug 8 – 15

$450 per night
Guest favorite

Condo in Greenport

4.83 out of 5 average rating, 141 reviews

Sound front condominium

Mar 14 – 21

$630 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 19 – 26

$693 per night
Guest favorite

Condo in Montauk

4.82 out of 5 average rating, 158 reviews

Coastline View Studio

Sep 25 – Oct 2

$999 per night
Superhost

Condo in Bridgehampton

4.92 out of 5 average rating, 13 reviews

Bridgehampton w/ Pool steps to town 3 bd 2.5 Bath

Nov 15 – 22

$385 per night
Superhost

Condo in Montauk

4.74 out of 5 average rating, 38 reviews

The Exclusive Resort in Montauk

Jun 5 – 12

$483 per night
Guest favorite

Condo in Montauk

4.88 out of 5 average rating, 17 reviews

1 BR Loft Apt- Montauk Manor- Pools, Tennis & Gym!

Jun 24 – Jul 1

$439 per night
Guest favorite

Condo in Montauk

4.82 out of 5 average rating, 87 reviews

Beautiful Condo on the Ocean Bluffs

Sep 19 – 26

$359 per night
Guest favorite

Condo in Greenport

5.0 out of 5 average rating, 90 reviews

"Breathtaking Waterfront Water's Edge view"

Feb 3 – 10

$403 per night
Superhost

Condo in Montauk

4.81 out of 5 average rating, 26 reviews

Montauk Sunsets

Jun 3 – 10

$357 per night

Destinations to explore