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Vacation rentals with a pool in Greenport

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Greenport

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

Jan 5 – 12

ﺩ.ﺇ1,212 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 17 – 24

ﺩ.ﺇ1,978 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

ﺩ.ﺇ1,111 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.

Jan 25 – Feb 1

ﺩ.ﺇ1,447 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.

Sep 12 – 19

ﺩ.ﺇ1,549 per night

Home in Hampton Bays

4.98 out of 5 average rating, 112 reviews

Beach House Feel - newly renovated backyard Oasis

You will love this sunny, completely renovated three bedroom ranch. It's beautifully decorated with beach and nautical themes throughout the house. You can cook or barbeque at home on your private deck or go out and enjoy the many award winning restaurants in the area. Come home from the beach or shopping and lounge by the pool. At night, gather around the fire pit while making smores or just admiring the stars. This house is perfect for families, couples, or a girls/guys getaway.

Sep 14 – 21

ﺩ.ﺇ2,901 per night

Home in Greenport

5.0 out of 5 average rating, 19 reviews

The Corwin House

Newly gut renovated 4 bed 3 bath home. Ultra high ceilings, large sunny windows and spacious open layouts throughout. Two masters with ensuite baths, walk in closets Downstairs, are two additional bedrooms with queen beds, and a third bath. Amenities include: free parking, large fenced in yard, pool, fire pit, grill Indoors: fireplace, central climate control, Bertazzoni appliances, smart tv, dishwasher, washer & dryer Pool is heated, heating cost not included.

May 10 – 17

ﺩ.ﺇ1,908 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

ﺩ.ﺇ1,436 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 9 – 16

ﺩ.ﺇ3,049 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

ﺩ.ﺇ984 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 2 – 9

ﺩ.ﺇ1,924 per night

Home in Water Mill

4.91 out of 5 average rating, 110 reviews

Beach Barn w/ Sauna and Heated Pool - Dog Friendly

Dog friendly (upon request) Hampton Beach Barn with heated pool and infrared sauna. POOL OPEN - May 3, 2024 - October 28, 2024 This impressive house, nestled within a rustic, woodland plot, promises a tranquil stay. Eclectic modern decor is complemented by striking rustic touches, such as Dutch-style farm doors, exposed beams, and vintage wood-burning stove.

Nov 26 – Dec 3

ﺩ.ﺇ4,120 per night

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Popular amenities for Greenport 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

ﺩ.ﺇ2,948 per night

Home in Sag Harbor

4.89 out of 5 average rating, 167 reviews

Kiddo Approved! Heated Pool/Hotub Renovated Home

Oct 15 – 22

ﺩ.ﺇ1,707 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

ﺩ.ﺇ1,296 per night

Home in Southampton

4.95 out of 5 average rating, 132 reviews

Waterview, PoolOpenNow! DogsFree+Kayaks+PingPong

May 27 – Jun 3

ﺩ.ﺇ2,972 per night

Home in Southold

5.0 out of 5 average rating, 11 reviews

Gorgeous home with heated gunnite pool!

Apr 18 – 25

ﺩ.ﺇ1,711 per night

Home in Cutchogue

4.96 out of 5 average rating, 76 reviews

Secluded Farmhouse - Studio Apartment Style Unit

Oct 21 – 28

ﺩ.ﺇ1,151 per night

Home in Mattituck

4.98 out of 5 average rating, 44 reviews

Modern farmhouse w/ pool, beach, horses and winery

Mar 17 – 24

ﺩ.ﺇ1,600 per night

Home in Cutchogue

5.0 out of 5 average rating, 25 reviews

North Fork paradise between beaches and vineyards

Jun 24 – Jul 1

ﺩ.ﺇ3,912 per night

Condo rentals with a pool

Condo in Greenport

5.0 out of 5 average rating, 90 reviews

"Breathtaking Waterfront Water's Edge view"

Oct 2 – 9

ﺩ.ﺇ2,067 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

ﺩ.ﺇ1,650 per night

Condo in Greenport

4.87 out of 5 average rating, 90 reviews

Waterfront Condo C-204 at The Cliffside Resort

Mar 27 – Apr 3

ﺩ.ﺇ2,002 per night

Condo in Greenport

4.81 out of 5 average rating, 88 reviews

Beautiful condo on Long Islands Northfolk

Mar 29 – Apr 5

ﺩ.ﺇ2,222 per night

Condo in Shelter Island Heights

5.0 out of 5 average rating, 5 reviews

Peaceful and Relaxing Waterfront.

Feb 15 – 22

ﺩ.ﺇ2,107 per night

Condo in Southampton

5.0 out of 5 average rating, 10 reviews

Newly Renovated Modern Townhouse w/Pool & Tennis

Jul 30 – Aug 6

ﺩ.ﺇ2,051 per night

Condo in Hampton Bays

4.97 out of 5 average rating, 33 reviews

A Unique Piece of Paradise, Water Front pool

Dec 1 – 8

ﺩ.ﺇ1,684 per night

Condo in Greenport

4.83 out of 5 average rating, 30 reviews

Two Bedroom Lawn Side 1st Floor Condo!

Dec 10 – 17

ﺩ.ﺇ1,428 per night

Home rentals with a private pool

Home in East Hampton

4.97 out of 5 average rating, 116 reviews

Explore the Water & Woods at a Relaxing Retreat

Dec 15 – 22

ﺩ.ﺇ3,349 per night

Home in East Hampton

4.77 out of 5 average rating, 13 reviews

Historical Estate Home with Backyard Pool

Oct 8 – 15

ﺩ.ﺇ3,977 per night

Home in Remsenburg

4.95 out of 5 average rating, 64 reviews

Experience a Quiet Hamptons Getaway

Feb 4 – 11

ﺩ.ﺇ2,204 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

ﺩ.ﺇ2,755 per night

Home in East Hampton

5.0 out of 5 average rating, 13 reviews

Saltbox with Separate Poolhouse in Northwest Woods

Apr 8 – 15

ﺩ.ﺇ2,739 per night

Home in East Hampton

4.79 out of 5 average rating, 39 reviews

Enchanting Home with Large Decks and Heated Pool

Mar 7 – 14

ﺩ.ﺇ2,114 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 8 – 15

ﺩ.ﺇ1,762 per night

Quick stats about vacation rentals with a pool in Greenport

Total rentals
20 properties
Wifi availability
20 properties include access to wifi
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Family-friendly rentals
10 properties are a good fit for families
Total number of reviews
490 reviews
Nightly prices starting at
ﺩ.ﺇ477 before taxes and fees

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