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Holiday rentals with a pool in Shelter Island

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Shelter Island

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

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.

24–31 Oct

$537 NZD 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

23–30 Oct

$1,235 NZD per night

Guest favourite

Condo in Greenport

4.91 out of 5 average rating, 107 reviews

Beachside Waterview 2Br Condo w/ Pool in Greenport

Relax in a pristine 2Br condo with ocean & pool views. Our remodeled apartment is part of high-end development nestled on LI Sound, just minutes from downtown Greenport. Sip a glass of wine while watching sunset, catch some rays on the beach or deep in the pool. 2 bedroom condo with ocean view, beach, and pool (seasonal) Comfortably sleeps 6 Private beach access year-around Pool (seasonal) Functional kitchenette 2 bathrooms, all toiletries Linens and towels are provided Smart TV AC/Heat

8–15 Oct

$562 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

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

$2,223 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

Condo in Greenport

4.93 out of 5 average rating, 124 reviews

Beautiful Waterview Condo on the North Fork of LI

Waterview luxury suite accommodates up to 6 guests with two bedrooms and two bathrooms located on the North Fork of Long Island at The Cliffside Resort Condominiums in Greenport, New York. This location is minutes from town as well as wineries and centrally located to the ferry which can take you to Shelter Island and the South Fork. The resort is well maintained with a pool , BBQ grills and private beach access as well as ample parking for guests.

10–17 Nov

$694 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

Apartment in Rocky Point

4.93 out of 5 average rating, 123 reviews

North shore Guest Room.

This apartment is our guest room with outside private entrance and off street parking. Apartment has a refrigerator, microwave, coffee maker, and toaster oven. Queen bed and a twin pullout couch bed is provided. The place is appropriate for a short stay as an affordable alternative to hotel stay.

3–8 Jun

$204 NZD per night

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Popular amenities for Shelter Island rentals with a pool

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Air conditioning

House rentals with a pool

Home in Sag Harbor

4.81 out of 5 average rating, 108 reviews

Sag Harbor Gem, private, 4 Bedrooms, Pool w Summer

6–13 Jun

$1,537 NZD per night

Guest favourite

Home in Cutchogue

4.96 out of 5 average rating, 190 reviews

Stunning Vinyard Views - Spring Special $475/Nt!

4–11 Feb

$1,518 NZD per night

Guest favourite

Home in Manorville

4.98 out of 5 average rating, 199 reviews

Ultimate House with Heated Pool, Hot Tub and Sauna

2–9 Oct

$1,087 NZD per night

Guest favourite

Home in Shelter Island

5.0 out of 5 average rating, 50 reviews

CASA GYPSEA - a chic and peaceful 3 bedroom house

29 Dec – 5 Jan

$1,089 NZD per night

Guest favourite

Home in Shelter Island

5.0 out of 5 average rating, 10 reviews

Spacious house with pool.

28 Oct – 4 Nov

$1,317 NZD per night

Guest favourite

Home in Shelter Island

4.92 out of 5 average rating, 52 reviews

Beautiful beach home with pool & water views!

25 Sep – 2 Oct

$1,631 NZD per night

Guest favourite

Home in Shelter Island

5.0 out of 5 average rating, 16 reviews

Family Friendly Oasis Steps to Water - Heated Pool

21–28 Mar

$2,024 NZD per night

Guest favourite

Home in Shelter Island

4.97 out of 5 average rating, 76 reviews

Modern, spacious SI home with pool

12–19 Mar

$1,603 NZD per night

Condo rentals with a pool

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

Guest favourite

Condo in Montauk

4.99 out of 5 average rating, 181 reviews

Montauk Waterfront Condo w/ Sunset Views

13–20 Sep

$902 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

Condo in Greenport

4.89 out of 5 average rating, 80 reviews

Seaside Escape w Pool, Private Beach & Patio

8–15 Apr

$1,053 NZD per night

Condo in Montauk

4.74 out of 5 average rating, 39 reviews

The Exclusive Resort in Montauk

19–26 Apr

$955 NZD per night

Guest favourite

Condo in Montauk

4.82 out of 5 average rating, 87 reviews

Beautiful Condo on the Ocean Bluffs

27 Mar – 3 Apr

$789 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 Southampton

4.94 out of 5 average rating, 16 reviews

Perfect Getaway at Sunny Modern Shampton Lake House

14–21 Jan

$1,311 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

Bungalow in East Hampton

4.93 out of 5 average rating, 99 reviews

East Hampton Ranch with Access to Clearwater Private Beach

21–28 May

$1,050 NZD per night

Quick stats about holiday rentals with a pool in Shelter Island

Total rentals
50 properties
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Pet-friendly rentals
20 properties allow pets
Family-friendly rentals
40 properties are a good fit for families
Total number of reviews
720 reviews
Nightly prices starting at
$286 NZD before taxes and fees

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