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.

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Guest favorite

Cottage in Southampton

4.95 out of 5 average rating, 85 reviews

Modern Southampton Cottage | Heated Pool & Peloton

Modern Hamptons cottage with mid-century modern interior, our 3 bedroom/ 2 bathroom cottage is set on manicured grounds and perfectly equipped for your stay. Heated gunite pool (summer months only) with retractable cover, Peloton bike and Central Air throughout. Newly renovated kitchen with high end appliances, large outdoor deck perfect for entertaining with new Weber grill. Private driveway accommodates 4 cars. 4 adult bicycles. 8 min ride to Southampton village. 15 min to Coopers Beach.

Guest favorite

Home in East Hampton

4.93 out of 5 average rating, 151 reviews

Large heated pool, games room, near private beach

Contemporary 4-bed + 4 1/2 bath home sitting on a park-like acre of gardens. Swim in the large pool (opens 04/25 and closes mid-October (there's an additional charge for heating - see below), relax in a hammock or bbq on the deck. Play ping-pong, darts, pool or take a 15 min walk to private bay beach to swim and paddle board. Or drive 15mins to the Atlantic beaches and visit picturesque Sag Harbor, Montauk. Reduced cleaning fee for small groups. RentReg RR-25-399 Local taxes included

Guest favorite

Cottage in Southampton

4.97 out of 5 average rating, 30 reviews

Newly Renovated Towd Point Beach Treasure

This stylish modern chic beach home is situated by the waters edge and one of the most idyllic beaches in the Hamptons. Make this home your summer escape and enjoy the cozy interior with brand new furniture throughout, hand selected by a renowned Hamptons interior designer. Outside, relax in the gunite pool or take the scenic walk to the shore. Along Towd Point, you'll find gorgeous beach homes, friendly neighbors, summer vibes and sunsets that will create lifelong memories!

Guest favorite

Apartment in Sag Harbor

4.93 out of 5 average rating, 116 reviews

PRIVATE BASEMENT APARTMENT WITH POOL IN SAG HARBOR

Beautiful basement apartment partially in-ground, with many windows and private entrance is located in Sag Harbor , 3 minutes from village and Heavens Bech by car or 15 minutes walking distance . The apartment has king size bed and comfortable sofa in the living room . In the kitchen you can find coffe maker , toaster , microwave, dishwasher, small fridge , hot plate for light cooking . Tv , WiFi , Airconditoining , access to pool from May till end of the September .

Superhost

Home in Hampton Bays

4.78 out of 5 average rating, 111 reviews

Private completely fenced in property. Near beach.

This beautiful custom expanded L ranch of 2800sf nested on a very private flat lot has 4 bedrooms, 3 bathrooms, living room, dining room areas with tons of light and privacy, movie theater. Gym and laundry room. The fenced in back yard comes with a lot of great features such as heated pool (for an extra fee), two level pergolas over a 20x40 concrete patio, full play set for the kids, fire pit, hammock area, outdoor shower and a cute pool house/lounge area with a loft!

Top guest favorite

Guest suite in East Hampton

4.96 out of 5 average rating, 163 reviews

B our guest! Central 2 all Prvt entrance Prvt Pool

Beautiful, bright, spacious King suite w fireplace, two bathrooms & private separate poolside entrance. We are just minutes to beaches, boating, golf, hiking, biking, yoga and wineries. Play games, grill or cozy up fireside w a good book/movie! The space is creatively designed with a nod to natural elements and luxe comfort. Sleep your very best on our super deluxe king sized bed w your choice of pillows. Complimentary coffee/tea/snacks and breakfast treats provided.

Top guest favorite

Home in East Hampton

4.98 out of 5 average rating, 130 reviews

Explore the Water & Woods at a Relaxing Retreat

Flick through records under soaring ceilings and hang out in the year-round hot tub at this East Hampton open-plan retreat. Unwind in the wooded backyard, take a dip in the pool or spa, detox in the sauna, grill on BBQ, relax in the movie-theatre seats to watch a film, then snuggle up to fireplace or firepit before drifting to sleep in super comfy beds. Minutes to village, beaches and hiking trails. Terrific for families & friends looking for a relaxing getaway.

Guest favorite

Home in Southampton

4.96 out of 5 average rating, 169 reviews

Waterview+Pool, FreeForDogs! Kayaks/PingPong/Bikes

Beachy casual feel-good home easily located at the entrance to The Hamptons. Lovely views of the Bay, Nightly Sunsets & birds! Launch our Kayaks at street's tiny beach flowing from Cold Spring Pond into Bay. Or cuddle by the fireplace and play our many available games. We provide soft sheets & towels for the showers and & beach...priding ourselves on your comfort! Our Private-Pool is heatable & plant-surrounded with Outdoor Shower.

Superhost

Home in Hampton Bays

4.95 out of 5 average rating, 129 reviews

Peaceful Retreat in Immaculate Architect’s House

This "like new" contemporary home features 4 bedrooms, 3.5 baths, open living spaces, soaring ceilings, abundant natural light, and a modern kitchen. Nestled in tranquil West Tiana Shores, minutes from bay & ocean beaches, and charming Hampton villages (Southampton, Westhampton, Quogue). The living room directly faces your private pool, cedar deck, and lush garden—a perfect getaway for vibrant summers and relaxing winters

Guest favorite

Apartment in Montauk

4.86 out of 5 average rating, 111 reviews

Recharge at our Renovated ocean front unit

Looking for a relaxing weekend to recharge on the beach? Then this newly renovated, bohemian-chic, apartment is perfect for you. Imagine waking up every morning to beautiful unobstructed ocean views and ending your night with a drink in hand watching the sunset. If you’re lucky, you might see some whales or dolphins breaching in the water right off our private beach. We would love to host you for your Montauk beach getaway.

Superhost

Home in Rocky Point

4.92 out of 5 average rating, 103 reviews

Luxury modern farmhouse with heated pool & hot tub

*pool is now open! This beautiful modern farmhouse is located on a one-acre lot and features a custom designed open-concept living space with vaulted ceilings that opens directly into a pool area. Hidden behind a bookshelf, you'll find a gorgeous game room with a piano and a pool table that can be easily converted into a ping pong table or working space. Please note that we do not allow weddings and events at this time.

Top guest favorite

Home in Southampton

5 out of 5 average rating, 74 reviews

SH Dream home with Heated Pool open from May 16

Beautiful three bedroom-three bathroom house situated on almost an acre. This newly renovated stylish home is located in North Sea - 1 mile drive to the Bay. Perfect for a relaxing get-away this Fall/Winter and for the upcoming Spring/Summer. Heated Pool is available/open from May 16th to October 14 - 2025)