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Holiday rentals with a pool in Bridgehampton

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Bridgehampton

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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Home in Sag Harbor

4.82 out of 5 average rating, 132 reviews

New! Sag Harbor Village Pool, Hot Tub &Beach House

New, immaculate, all-season home by the beach with crisp designer details. Every detail was considered for maximum enjoyment. The heated saltwater pool (open April-Nov) hot tub, fenced in yard & deck gets sun all day. Located in the village of Sag Harbor, steps from the Bay and Main Street & all the Hamptons has to offer. Come feel the vacation vibes as soon as you arrive. The central location, luxurious finishes, breathtaking sunsets on the sandy beach make this the perfect year-round getaway.

31 Oct – 7 Nov

$1,068 SGD per night

Guest favourite

Flat in Sagaponack

4.97 out of 5 average rating, 38 reviews

Hamptons elegant and comfortable apartment

Enjoy your stay in this beautifully decorated and completely private basement apartment - with all original artwork- in the center of the Hamptons with the added convenience of being close to major towns and beaches. Large bedroom with comfortable king sized bed and high quality mattress and linen. Large-screen smart TV with many channels. Closet space, well equipped kitchenette, bathroom with glass-enclosed shower. Seating area for 4 and second large-screen smart-TV with comfy oversized couch.

24–31 Dec

$676 SGD per night

Guest favourite

Guest house in Southampton

4.96 out of 5 average rating, 136 reviews

Wonderful Private Spacious Pool House

Light, open, spacious and private pool house less than 1/2 mile from the bay beach and 4 miles to ocean beaches. Close to Southampton, Sag Harbor, and Water Mill. Families love it as do our many girl getaways. Pool and deck and BBQ and umbrellas and pool toys and lounge chairs are for your exclusive enjoyment too. Enough beds to sleep 6, but we allow up to 3 additional guests for a total of 9 with an additional fee. Portable beds and linens will be provided. Can’t book just 1 weekend night.

21–28 Mar

$733 SGD per night

Apartment in Bridgehampton

4.92 out of 5 average rating, 13 reviews

Bridgehampton w/ Pool steps to town 3 bd 2.5 Bath

Beautiful duplex corner townhouse unit completely renovated in 2021 & in the heart of Bridgehampton Village. 2 min walk to shops, restaurants, main street and a bicycle ride to the beach. Situated all the way at the end of the building it provides ample privacy with Pool open July 4 - Labor Day only. Free parking (2 spots) w/ extra guest parking. Central air conditioning, private patio, ring doorbell/cam, self check in, curated kitchen w/ all supplies. Linens, towels, soap & shamp included

15–22 Nov

$596 SGD per night

Guest favourite

Guest suite in East Hampton

4.98 out of 5 average rating, 117 reviews

Hamptons Dream Suite

Hampton's Dream Suite- Is a guest suite in East Hampton, NY. From relaxing by the pool, to taking a day trip to Montauk, or visiting some of the best beaches in the Hamptons, the opportunities here are endless! It offers a bedroom with a Queen size Select Comfort bed, living room has two queen sofa beds and a full bathroom. It has a Kitchenette, Central AC/Heat with a 65" smart TV with surround sound and DVD, Blue ray and Xbox Games . There is also at TV and blue Ray player in the bedroom.

14–21 Jun

$475 SGD per night

Guest favourite

Cottage in East Hampton

5.0 out of 5 average rating, 30 reviews

Storybook Cottage Seconds to East Hampton Village

Beach Cottage at edge of East Hampton Village. This fresh and bright cottage with three bedrooms and two new bathrooms is a compact and convenient jewel box with everything you'd expect in the Hamptons - including a beautiful pool with built-in hot tub. Just blocks from the heart of East Hampton on a quiet no-traffic cul-de-sac, not far from beach, shopping, dining and train... sparkling kitchen with new 'retro style' appliances, gleaming hardwood floors throughout, and a cozy front porch.

23–30 Oct

$742 SGD per night

Guest favourite

Guest suite in East Hampton

4.96 out of 5 average rating, 142 reviews

Be our guest! Peaceful private proximity to all.

Beautiful, bright, spacious king suite w fireplace, two bathrooms & private separate poolside entrance in the country. We are just minutes to golf, hiking, biking, yoga, wineries and beaches. Play games, grill poolside or cozy up fireside w a good book or 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.

23 Feb – 2 Mar

$470 SGD per night

Guest house in Bridgehampton

4.82 out of 5 average rating, 61 reviews

Central Hamptons Guesthouse

This is a quiet + cozy guesthouse located at the rear corner of the property. The Guesthouse is nearby both Bridgehampton and Sag Harbor and has its own private dining and seating area. If you would like to use hot tub it is private for the guesthouse use only, their is also a separate pool area available for guest use however please be respectful of the other guests and the neighbors. The pool also is open for the season as of Mar24 and the hot tub is available for use year around.

7–14 May

$365 SGD per night

Guest favourite

Home in East Hampton

4.97 out of 5 average rating, 116 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.

9–16 Nov

$1,242 SGD per night

Guest favourite

Flat in Sag Harbor

4.95 out of 5 average rating, 83 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 .

15–22 May

$322 SGD per night

Guest favourite

Guest suite in East Hampton

4.89 out of 5 average rating, 222 reviews

Private Cozy Cottage with Pool / Private Beach

**POOL CLOSES SEPTEMBER 30TH** **POOL opens last week of May** This is a guest house for 1 or 2 adults. Its separate from the main house. Kids are allowed but must bring own sleeping arrangements. You do NOT have to do any chores before checking out. **PETS NOT ALLOWED** I hate to do this but someone ruined it for everyone. Max Occupancy: 4 Guests can only bring 1 vehicle since there is not enough room in the driveway

3–10 Oct

$365 SGD per night

Guest favourite

Home in Sag Harbor

4.85 out of 5 average rating, 250 reviews

Exclusive Sag Harbor Compound

A private country compound in heart of Sag Harbor. House just gut renovated with all top of line (all Wolf and Subzero appliances). The main house is 3 bedrooms, 3.5 bath main house PLUS separate large guest cottage (with a King bed, bar fridge, and full bathroom). Gunite pool (i.e., salt chlorinated which makes it feels like clean freshwater). Walk to town, bay beach, public tennis courts, 1000 acre nature preserve.

4–11 Dec

$713 SGD per night

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Popular amenities for Bridgehampton rentals with a pool

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Air conditioning

House rentals with a pool

Guest favourite

Home in Shelter Island

4.97 out of 5 average rating, 194 reviews

Huge Island Getaway Pool HotTub Walk To Beach

6–13 Feb

$1,337 SGD per night

Guest favourite

Home in Hampton Bays

4.98 out of 5 average rating, 112 reviews

Beach House Feel - newly renovated backyard Oasis

8–15 Oct

$736 SGD per night

Guest favourite

Home in Southampton

4.88 out of 5 average rating, 193 reviews

Secluded Southampton Luxury Estate. 286

25 Oct – 1 Nov

$1,545 SGD per night

Guest favourite

Home in Southampton

4.96 out of 5 average rating, 130 reviews

Waterview, PoolOpenNow! DogsFree+Kayaks+PingPong

7–14 Jun

$1,486 SGD per night

Guest favourite

Home in Southampton

5.0 out of 5 average rating, 56 reviews

Dream home in SH with heated Pool OPEN from May 4

25 Jan – 1 Feb

$678 SGD per night

Guest favourite

Home in Bridgehampton

5.0 out of 5 average rating, 19 reviews

Chic + Crisp Bridgehampton Home with Heated Pool

8–15 Feb

$1,017 SGD per night

Guest favourite

Home in Southampton

5.0 out of 5 average rating, 22 reviews

Renovated Southampton Home+Pool

17–24 Feb

$494 SGD per night

Home in East Hampton

5.0 out of 5 average rating, 5 reviews

Hampton Oasis with private Tennis, Pool, Theater

6–13 Dec

$942 SGD per night

Apartment rentals with a pool

Guest favourite

Apartment in Greenport

4.91 out of 5 average rating, 107 reviews

Beachside Waterview 2Br Condo w/ Pool in Greenport

25 Oct – 1 Nov

$392 SGD per night

Guest favourite

Apartment in Montauk

4.99 out of 5 average rating, 181 reviews

Montauk Waterfront Condo w/ Sunset Views

18–25 Mar

$521 SGD per night

Guest favourite

Apartment in Greenport

4.92 out of 5 average rating, 125 reviews

Beautiful Waterview Condo on the North Fork of LI

10–17 Nov

$532 SGD per night

Apartment in Greenport

4.83 out of 5 average rating, 145 reviews

Sound front condominium

9–16 Oct

$603 SGD per night

Guest favourite

Apartment in Montauk

4.95 out of 5 average rating, 107 reviews

Deluxe Studio Apt@The Montauk Manor

26 Aug – 2 Sep

$658 SGD per night

Apartment in Montauk

4.8 out of 5 average rating, 232 reviews

Montauk Royal Atlantic Beach Resort North

20–27 Jul

$727 SGD per night

Guest favourite

Apartment in Montauk

4.82 out of 5 average rating, 158 reviews

Coastline View Studio

26 Oct – 2 Nov

$1,555 SGD per night

Apartment in Greenport

4.89 out of 5 average rating, 80 reviews

Seaside Escape w Pool, Private Beach & Patio

22–29 Oct

$576 SGD per night

Home rentals with a private pool

Guest favourite

Home in Remsenburg

4.95 out of 5 average rating, 64 reviews

Experience a Quiet Hamptons Getaway

6–13 Jan

$817 SGD per night

Home in East Hampton

5.0 out of 5 average rating, 13 reviews

Saltbox with Separate Poolhouse in Northwest Woods

6–13 Apr

$1,015 SGD per night

Home in Southampton

4.94 out of 5 average rating, 16 reviews

Perfect Getaway at Sunny Modern Shampton Lake House

14–21 Jan

$1,021 SGD per night

Home in East Hampton

4.79 out of 5 average rating, 39 reviews

Enchanting Home with Large Decks and Heated Pool

25 Oct – 1 Nov

$784 SGD per night

Bungalow in East Hampton

4.93 out of 5 average rating, 99 reviews

East Hampton Ranch with Access to Clearwater Private Beach

14–21 May

$653 SGD per night

Quick stats about holiday rentals with a pool in Bridgehampton

Total rentals
160 properties
Rentals with dedicated workspaces
90 properties have a dedicated workspace
Pet-friendly rentals
90 properties allow pets
Family-friendly rentals
140 properties are a good fit for families
Total number of reviews
1.6K reviews
Nightly prices starting at
$259 SGD before taxes and fees

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