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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.

12–19 Nov

$1,343 NZD per night

Guest favourite

Apartment 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.

22–29 Dec

$896 NZD per night

Guest favourite

Guesthouse 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.

11–18 Apr

$937 NZD 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

$618 NZD 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

$954 NZD 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.

24–31 Jul

$1,118 NZD per night

Guest favourite

Home in Sag Harbor

4.94 out of 5 average rating, 101 reviews

Sag Harbor Village Cottage with Pool

Situated on a half-acre of land, this classic shingle cottage with brand new designer interiors offers the ideal Hamptons getaway. Located in the picturesque village of Sag Harbor, less than a mile from town, bay beaches, and tennis. 10 minute drive to Wolffer & ocean beaches. 4 bedrooms, 2 modern bathrooms and pool with mature landscaping offers a relaxing escape. Please read the additional disclosures, guidelines, and rules. No events, no parties, no smoking – no exceptions!

12–19 Jun

$1,949 NZD 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.

21–28 Dec

$1,605 NZD per night

Guest favourite

Apartment 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

$421 NZD 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

$463 NZD 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

$936 NZD per night

Guest favourite

Cottage in Water Mill

4.98 out of 5 average rating, 55 reviews

Head of Pond House - Waterfront Cottage

Charming Cottage with lake access. Close to beaches, wineries, restaurants and all the Hamptons have to offer. One bedroom, and two king beds (one in the loft area), one bath cottage with WIFI and projector. Kitchen including fridge, stove, oven and dishwasher for your perfect weekend or weeklong getaway. Ideal for anyone looking for a peaceful oasis while close to all the action of the East End.

8–15 May

$685 NZD per night

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Popular amenities for Bridgehampton rentals with a pool

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House rentals with a pool

Guest favourite

Home in East Hampton

4.87 out of 5 average rating, 188 reviews

Heated Saltwater Pool, Walk to Beach, Dog Friendly

24–31 Oct

$537 NZD per night

Guest favourite

Home in Hampton Bays

4.98 out of 5 average rating, 112 reviews

Beach House Feel - newly renovated backyard Oasis

25 Oct – 1 Nov

$958 NZD per night

Guest favourite

Home in Southampton

4.88 out of 5 average rating, 193 reviews

Secluded Southampton Luxury Estate. 286

8–15 Oct

$1,995 NZD per night

Guest favourite

Home in Southampton

4.95 out of 5 average rating, 246 reviews

Southampton Village Classic Summer Special!

25 Oct – 1 Nov

$1,951 NZD 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

$1,318 NZD per night

Guest favourite

Home in Sag Harbor

4.89 out of 5 average rating, 71 reviews

Sag Harbor Wonder, 3 bedroom 2 Bath & Heated Pool

7–14 Oct

$1,744 NZD per night

Guest favourite

Home in Southampton

5.0 out of 5 average rating, 41 reviews

Bay View Stunner, Modern 6 Bedroom w Heated Pool

18–25 May

$1,798 NZD per night

Guest favourite

Home in Southampton

5.0 out of 5 average rating, 21 reviews

Renovated Southampton Home+Pool

12–19 Mar

$684 NZD per night

Condo rentals with a pool

Guest favourite

Condo in Greenport

4.91 out of 5 average rating, 107 reviews

Beachside Waterview 2Br Condo w/ Pool in Greenport

8–15 Oct

$562 NZD per night

Guest favourite

Condo in Montauk

4.99 out of 5 average rating, 181 reviews

Montauk Waterfront Condo w/ Sunset Views

17–24 Mar

$679 NZD per night

Guest favourite

Condo in Greenport

4.93 out of 5 average rating, 124 reviews

Beautiful Waterview Condo on the North Fork of LI

10–17 Nov

$694 NZD per night

Condo in Greenport

4.83 out of 5 average rating, 145 reviews

Sound front condominium

9–16 Oct

$782 NZD per night

Guest favourite

Condo in Montauk

4.95 out of 5 average rating, 107 reviews

Deluxe Studio Apt@The Montauk Manor

30 Mar – 6 Apr

$522 NZD per night

Condo in Montauk

4.8 out of 5 average rating, 231 reviews

Montauk Royal Atlantic Beach Resort North

20–27 Jul

$899 NZD per night

Guest favourite

Condo in Montauk

4.82 out of 5 average rating, 158 reviews

Coastline View Studio

26 Oct – 2 Nov

$1,947 NZD per night

Guest favourite

Condo in Greenport

5.0 out of 5 average rating, 90 reviews

"Breathtaking Waterfront Water's Edge view"

5–12 Jan

$821 NZD 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

24–31 Jan

$1,040 NZD per night

Home in East Hampton

5.0 out of 5 average rating, 13 reviews

Saltbox with Separate Poolhouse in Northwest Woods

4–11 Apr

$1,304 NZD per night

Home in East Hampton

4.79 out of 5 average rating, 39 reviews

Enchanting Home with Large Decks and Heated Pool

2–9 Apr

$1,076 NZD 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

$1,320 NZD per night

Bungalow in East Hampton

4.93 out of 5 average rating, 99 reviews

East Hampton Ranch with Access to Clearwater Private Beach

15–22 May

$898 NZD 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
$320 NZD before taxes and fees

Destinations to explore