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Vacation rentals with a pool in Sag Harbor

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Sag Harbor

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.

Oct. 31 – Nov. 7

$1,134 CAD per night

Guest favourite

Home in Shelter Island

4.97 out of 5 average rating, 194 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.

Feb. 6 – 13

$1,414 CAD per night

Guest favourite

Home in East Hampton

4.92 out of 5 average rating, 128 reviews

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

Contemporary 4-bed + 4 1/2 bath home sitting on a park-like acre of gardens. Swim in the large pool (open 04/19 - additional charge for heating - see below), relax in a hammock or bbq on the deck. Play ping-pong, darts, pool, shoot hoops, or take a 15 minute walk to the private (and empty) bay beach where you can use my paddle board. Or drive to the famous Atlantic beaches and visit picturesque Sag Harbor, Montauk. Reduced cleaning fee for small groups. RentReg 22-1590 Local taxes included

Oct. 23 – 30

$1,002 CAD 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.

Mar. 21 – 28

$760 CAD 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.

Jun. 14 – 21

$501 CAD 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.

Oct. 23 – 30

$774 CAD per night

Guest favourite

Home in Sag Harbor

5.0 out of 5 average rating, 9 reviews

Sunny Sag Harbor Retreat

Relax in our charming, bright, fully-equipped house 1.5 miles from Sag Harbor Village and bay beaches, 5 miles from ocean beaches, and 2 miles from Wölffer Vineyard. Enjoy the large, sunny deck and swimming pool, beautiful new kitchen, light-filled den, outdoor lounging and dining areas, outdoor shower, evening sunsets, and starry skies overlooking a 600 acre nature preserve. Beach towels, folding beach chairs, beach umbrella, small cooler, sand toys, and many books and games are included.

Dec. 31 – Jan. 7

$929 CAD 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.

Jun. 6 – 13

$835 CAD 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.

Nov. 9 – 16

$1,302 CAD 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 .

May 15 – 22

$341 CAD 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

Oct. 3 – 10

$376 CAD 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.

Dec. 4 – 11

$759 CAD per night

Vacation rentals for every style

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Apartments

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Cottages

Quaint homes, peaceful surroundings

Popular amenities for Sag Harbor rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Guest favourite

Home in Hampton Bays

4.98 out of 5 average rating, 112 reviews

Beach House Feel - newly renovated backyard Oasis

Oct. 8 – 15

$787 CAD per night

Guest favourite

Home in Southampton

4.88 out of 5 average rating, 193 reviews

Secluded Southampton Luxury Estate. 286

Oct. 25 – Nov. 1

$1,618 CAD per night

Guest favourite

Home in Southampton

4.96 out of 5 average rating, 130 reviews

Waterview, PoolOpenNow! DogsFree+Kayaks+PingPong

Jun. 7 – 14

$1,544 CAD per night

Home in East Hampton

4.88 out of 5 average rating, 101 reviews

Gorgeous East Hampton Getaway

Nov. 8 – 15

$1,147 CAD per night

Guest favourite

Home in Southampton

5.0 out of 5 average rating, 56 reviews

Dream home in SH with heated private Pool

Jan. 25 – Feb. 1

$757 CAD per night

Guest favourite

Home in Sag Harbor

4.84 out of 5 average rating, 45 reviews

Modern Home in Sag Harbor, NY

May 29 – Jun. 5

$1,430 CAD per night

Guest favourite

Home in Sag Harbor

4.91 out of 5 average rating, 33 reviews

Sag Harbor Amazing Beach house Awaits!

Feb. 21 – 28

$936 CAD per night

Guest favourite

Home in Sag Harbor

4.96 out of 5 average rating, 24 reviews

The Hamptons Casita: Modern Elegance Meets Cozy

Jun. 17 – 24

$1,463 CAD 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

Oct. 25 – Nov. 1

$418 CAD per night

Guest favourite

Condo in Montauk

4.99 out of 5 average rating, 181 reviews

Montauk Waterfront Condo w/ Sunset Views

Mar. 18 – 25

$551 CAD per night

Guest favourite

Condo in Greenport

4.92 out of 5 average rating, 125 reviews

Beautiful Waterview Condo on the North Fork of LI

Nov. 10 – 17

$563 CAD per night

Condo in Greenport

4.83 out of 5 average rating, 145 reviews

Sound front condominium

Oct. 9 – 16

$634 CAD per night

Guest favourite

Condo in Montauk

4.95 out of 5 average rating, 107 reviews

Deluxe Studio Apt@The Montauk Manor

Aug. 26 – Sep. 2

$679 CAD per night

Condo in Montauk

4.8 out of 5 average rating, 232 reviews

Montauk Royal Atlantic Beach Resort North

Jul. 20 – 27

$729 CAD per night

Guest favourite

Condo in Montauk

4.82 out of 5 average rating, 158 reviews

Coastline View Studio

Oct. 26 – Nov. 2

$1,579 CAD 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

Nov. 15 – 22

$675 CAD 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

Jan. 6 – 13

$844 CAD per night

Home in Southampton

4.94 out of 5 average rating, 16 reviews

Perfect Getaway at Sunny Modern Shampton Lake House

Jan. 14 – 21

$1,063 CAD per night

Home in East Hampton

5.0 out of 5 average rating, 13 reviews

Saltbox with Separate Poolhouse in Northwest Woods

Apr. 6 – 13

$1,058 CAD per night

Home in East Hampton

4.79 out of 5 average rating, 39 reviews

Enchanting Home with Large Decks and Heated Pool

Oct. 25 – Nov. 1

$872 CAD 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 14 – 21

$728 CAD per night

Quick stats about vacation rentals with a pool in Sag Harbor

Total rentals
130 properties
Rentals with dedicated workspaces
70 properties have a dedicated workspace
Pet-friendly rentals
50 properties allow pets
Family-friendly rentals
110 properties are a good fit for families
Total number of reviews
1.7K reviews
Nightly prices starting at
$123 CAD before taxes and fees

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