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Vacation 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.

Nov 19 – 26

G$156,983 GYD per night

Home in East Hampton

4.87 out of 5 average rating, 188 reviews

Heated Saltwater Pool, Walk to Beach, Dog Friendly

Meticulously cleaned home. Tranquil family neighborhood in historic artist's beach community. Wood burning fireplace. Private fenced-in backyard . Heated saltwater pool in summer. Half mile to private bay beach, bike great trails & savor delicious meals prepared in fully equipped kitchen. Don’t miss Clearwater Beach's stunning sunset. Easy living home.Welcoming to all respectful families & guests.East Hampton's best restaurants are nearby. Smoke free.Small dogs permitted.Rental Registry 23-625.

Oct 31 – Nov 7

G$47,348 GYD per night

Home in Watermill

4.88 out of 5 average rating, 128 reviews

Modern House close to the beach

This modern home has all the amenities and comfort you would expect. You are 5 minutes from Southampton Village, 5 minutes from Flying Point Beach by car. Spacious back yard with beautiful patio furniture which gives onto beautiful pond. Fully equipped kitchen with Wolf stove. Lots of sun on this property. Quiet back patio area with barbecue and patio furniture. Fireplace available in the winter months. We use cotton linen and towels. Pool open in May. Pool heating is an additional cost.

Oct 13 – 20

G$227,807 GYD per night

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.

Feb 13 – 20

G$112,548 GYD per night

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.

Jun 14 – 21

G$61,139 GYD per night

Cottage in Southampton

4.96 out of 5 average rating, 164 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.

Sep 6 – 13

G$222,787 GYD per night

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.

Aug 16 – 23

G$136,806 GYD per night

Home in Sag Harbor

4.89 out of 5 average rating, 166 reviews

Kiddo Approved! Heated Pool/Hotub Renovated Home

Family friendly Sag Harbor one level beach house close to Main Street. Heated pool (for a fee), hot tub, enclosed grass yard, kids play area with sandbox and toys, crib, highchair, outdoor fireplace, outdoor shower, yard is fenced and gated with separate safety fence for pool area. Backs up to a nature preserve for privacy. Quiet Neighborhood. Short drive to the beach and Main Street. Pool open April 13th-Oct 1. Pool can be heated June-August (for a fee). Hot Tub open April- November.

Oct 18 – 25

G$97,132 GYD per night

Home in Sag Harbor

4.94 out of 5 average rating, 102 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!

May 26 – Jun 2

G$212,708 GYD per night

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.

Nov 4 – 11

G$190,565 GYD per night

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

Oct 10 – 17

G$56,017 GYD per night

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.

Dec 20 – 27

G$159,543 GYD per night

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Popular amenities for Bridgehampton rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Home in East Hampton

4.92 out of 5 average rating, 128 reviews

Heated pool, games room, near beach, kid-friendly

Oct 23 – 30

G$144,357 GYD per night

Home in Sag Harbor

4.98 out of 5 average rating, 88 reviews

Perfection in Sag Harbor 5 Br 1 block from water

Feb 3 – 10

G$133,105 GYD per night

Home in Southampton

5.0 out of 5 average rating, 57 reviews

Dream home in SH with Heated Pool OPEN from May 4

Feb 13 – 20

G$109,511 GYD per night

Home in Southampton

5.0 out of 5 average rating, 23 reviews

Renovated Southampton Home+Pool

Apr 3 – 10

G$75,883 GYD per night

Home in Bridgehampton

5.0 out of 5 average rating, 19 reviews

Chic + Crisp Bridgehampton Home with Heated Pool

May 23 – 30

G$198,147 GYD per night

Home in East Hampton

5.0 out of 5 average rating, 13 reviews

East hampton 3 bedroom home w/ pool great location

Mar 10 – 17

G$108,058 GYD per night

Home in Water Mill

4.92 out of 5 average rating, 91 reviews

Peaceful 1850s barn w/Pool

Apr 19 – 26

G$169,709 GYD per night

Home in Sag Harbor

4.96 out of 5 average rating, 24 reviews

The Hamptons Casita: Summer Meets Perfect Pool

Jun 12 – 19

G$201,243 GYD per night

Condo rentals with a pool

Condo in Greenport

4.91 out of 5 average rating, 107 reviews

Beachside Waterview 2Br Condo w/ Pool in Greenport

Oct 20 – 27

G$63,232 GYD per night

Condo in Montauk

4.99 out of 5 average rating, 181 reviews

Montauk Waterfront Condo w/ Sunset Views

Apr 2 – 9

G$91,237 GYD per night

Condo in Montauk

4.95 out of 5 average rating, 107 reviews

Deluxe Studio Apt@The Montauk Manor

Apr 23 – 30

G$66,857 GYD per night

Condo in Greenport

4.83 out of 5 average rating, 145 reviews

Sound front condominium

Apr 16 – 23

G$150,880 GYD per night

Condo in Greenport

4.92 out of 5 average rating, 125 reviews

Beautiful Waterview Condo on the North Fork of LI

May 24 – 31

G$137,763 GYD per night

Condo in Montauk

4.8 out of 5 average rating, 232 reviews

Montauk Royal Atlantic Beach Resort North

Aug 1 – 8

G$112,686 GYD per night

Condo in Montauk

4.82 out of 5 average rating, 158 reviews

Coastline View Studio

Nov 2 – 9

G$238,667 GYD per night

Condo in Bridgehampton

4.92 out of 5 average rating, 13 reviews

Bridgehampton w/ Pool steps to town 3 bd 2.5 Bath

Dec 2 – 9

G$63,231 GYD per night

Home rentals with a private pool

Home in Remsenburg

4.95 out of 5 average rating, 64 reviews

Experience a Quiet Hamptons Getaway

Apr 2 – 9

G$125,392 GYD per night

Home in East Hampton

5.0 out of 5 average rating, 13 reviews

Saltbox with Separate Poolhouse in Northwest Woods

Apr 5 – 12

G$155,860 GYD per night

Home in Southampton

4.94 out of 5 average rating, 16 reviews

Perfect Getaway at Sunny Modern Shampton Lake House

Jan 13 – 20

G$156,780 GYD per night

Home in East Hampton

4.79 out of 5 average rating, 39 reviews

Enchanting Home with Large Decks and Heated Pool

Jan 17 – 24

G$120,298 GYD per night

Bungalow in East Hampton

4.93 out of 5 average rating, 99 reviews

East Hampton Ranch with Access to Clearwater Private Beach

May 5 – 12

G$100,281 GYD per night

Quick stats about vacation 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
G$39,707 GYD before taxes and fees

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