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Vacation rentals with a pool in Greenport West

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Greenport West

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

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Condo in Greenport

4.89 out of 5 average rating, 81 reviews

Seaside Escape w Pool, Private Beach & Patio

Located on a small bluff overlooking the Long Island Sound, this waterfront condo is minutes from the center of town. Discover farms, wineries, restaurants & shops or just soak up the sun on your private beach. On the North Fork, farmland and wineries unroll all the way to the ocean. ⚓️ Greenport is a historic seaport located on Long Island's North Fork. 🏖 Waterfront private deck, balcony, grills, private beach, pool, parking ⛴ Ferry access to the South Fork, Shelter Island & Connecticut

Nov 6 – 13

G$90,955 GYD per night

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

G$144,003 GYD per night

Condo in Greenport

4.9 out of 5 average rating, 108 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

Oct 20 – 27

G$63,077 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 12 – 19

G$62,946 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.

Apr 21 – 28

G$64,759 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.

Sep 24 – Oct 1

G$215,844 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!

Jun 11 – 18

G$213,884 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 16 – 23

G$212,181 GYD per night

Condo in Greenport

4.92 out of 5 average rating, 125 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.

Apr 19 – 26

G$81,517 GYD per night

Home in Cutchogue

4.96 out of 5 average rating, 190 reviews

Private Oasis W/Stunning Vinyard And Pool Views

Enjoy spectacular wine country sunset views from the living room that extend to the gorgeous saltwater gunite pool and spa. (Please note THE POOL AND SPA (attached hot tub) are OPEN FROM MAY 1 - OCTOBER 15 only). Beautifully decorated, comfortable home with an updated chef's kitchen and fireplace. Fabulous restaurants, wineries, farms, beaches and exquisite small towns all nearby. Simply put, a magical, peaceful paradise for you and your group.

Mar 7 – 14

G$173,052 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$55,879 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 8 – 15

G$109,191 GYD per night

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Popular amenities for Greenport West rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Home in East Hampton

4.93 out of 5 average rating, 141 reviews

1800 Historical East Hampton Home, 1 Mile to Town!

Nov 15 – 22

G$167,372 GYD per night

Home in Hampton Bays

4.98 out of 5 average rating, 112 reviews

Beach House Feel - newly renovated backyard Oasis

Jul 18 – 25

G$175,399 GYD per night

Home in Southampton

4.95 out of 5 average rating, 132 reviews

Waterview, PoolOpenNow! DogsFree+Kayaks+PingPong

May 26 – Jun 2

G$186,149 GYD per night

Home in East Hampton

4.88 out of 5 average rating, 101 reviews

Gorgeous East Hampton Getaway

Oct 10 – 17

G$179,477 GYD per night

Home in East Hampton

4.87 out of 5 average rating, 188 reviews

Heated Saltwater Pool, Walk to Beach, Dog Friendly

Dec 27 – Jan 3

G$73,571 GYD per night

Home in Sag Harbor

4.82 out of 5 average rating, 132 reviews

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

Nov 9 – 16

G$156,598 GYD per night

Home in Southold

5.0 out of 5 average rating, 10 reviews

Gorgeous home with heated gunnite pool!

Mar 27 – Apr 3

G$90,647 GYD per night

Home in Shelter Island

5.0 out of 5 average rating, 50 reviews

CASA GYPSEA - a chic and peaceful 3 bedroom house

Jan 7 – 14

G$128,749 GYD per night

Condo rentals with a pool

Condo in Montauk

4.99 out of 5 average rating, 181 reviews

Montauk Waterfront Condo w/ Sunset Views

Feb 28 – Mar 7

G$79,712 GYD per night

Condo in Montauk

4.95 out of 5 average rating, 108 reviews

Deluxe Studio Apt@The Montauk Manor

Nov 5 – 12

G$36,106 GYD per night

Condo in Montauk

4.8 out of 5 average rating, 232 reviews

Montauk Royal Atlantic Beach Resort North

Aug 12 – 19

G$112,409 GYD per night

Condo in Montauk

4.82 out of 5 average rating, 158 reviews

Coastline View Studio

Nov 4 – 11

G$238,080 GYD per night

Condo in Greenport

5.0 out of 5 average rating, 90 reviews

"Breathtaking Waterfront Water's Edge view"

Mar 3 – 10

G$97,409 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

Nov 18 – 25

G$94,003 GYD per night

Condo in Montauk

4.82 out of 5 average rating, 87 reviews

Beautiful Condo on the Ocean Bluffs

Mar 23 – 30

G$95,476 GYD per night

Condo in Montauk

4.74 out of 5 average rating, 39 reviews

The Exclusive Resort in Montauk

Dec 11 – 18

G$115,215 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 4 – 11

G$125,084 GYD per night

Home in East Hampton

5.0 out of 5 average rating, 13 reviews

Saltbox with Separate Poolhouse in Northwest Woods

Apr 7 – 14

G$155,477 GYD per night

Home in Southampton

4.94 out of 5 average rating, 16 reviews

Perfect Getaway at Sunny Modern Shampton Lake House

Jan 1 – 8

G$156,395 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 1 – 8

G$120,002 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 7 – 14

G$100,034 GYD per night

Quick stats about vacation rentals with a pool in Greenport West

Total rentals
70 properties
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
60 properties are a good fit for families
Total number of reviews
1.7K reviews
Nightly prices starting at
G$27,101 GYD before taxes and fees

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