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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

Nov 6 – 13

R8,063 ZAR 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

R5,592 ZAR 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.

Jul 18 – 25

R15,549 ZAR 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

R18,960 ZAR per night

Condo in Greenport

5.0 out of 5 average rating, 90 reviews

"Breathtaking Waterfront Water's Edge view"

" Breathtaking Waterfront Water's Edge condominium. Newly renovated! Relax and enjoy this beautiful, luxurious space. Suite B-204 accommodates 6 guests very comfortably. Two bedrooms, two bathrooms, living room with sofa (pull-out bed), kitchen area, eating area with chairs- all newly renovated. Located on the North Fork of Long Island, Cliffside Resort Condominiums in Greenport, New York." So many activities to choose from nearby and in the quaint village of Greenport!

Mar 3 – 10

R8,635 ZAR per night

Home in Southold

5.0 out of 5 average rating, 10 reviews

Gorgeous home with heated gunnite pool!

Built in 1928, this gorgeous home is fully equipped to host your getaway. You're within easy walking distance of Horton's Lighthouse, where lovely beach walks and stunning sunsets await you. The local wineries are all within short drives of this lovely retreat. Enjoy the new heated gunnite pool with plenty of poolside seating. The family friendly layout features plenty of seating inside and out. You're just 100 yards north of a public beach, come enjoy the sunsets!

Mar 27 – Apr 3

R8,036 ZAR 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

R7,226 ZAR 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

R15,341 ZAR per night

Home in Cutchogue

5.0 out of 5 average rating, 24 reviews

North Fork paradise between beaches and vineyards

Kick back and relax in this calm, stylish retreat. Nestled between vineyards and farmlands, this newly renovated mid-century ranch with a beautiful 14x50' heated salt water pool is a short hop to beautiful beaches, wineries, restaurants, and farm stands. Enjoy nature in a secluded park-like setting and explore everything the NoFo has to offer all year around. Please note that there are no parties, gatherings or unannounced guests allowed.

Nov 7 – 14

R11,779 ZAR per night

Home in Cutchogue

4.96 out of 5 average rating, 76 reviews

Secluded Farmhouse - Studio Apartment Style Unit

Beautiful, quiet, studio apartment-style unit (private entrance w/full bath) tucked away in a modern farmhouse on a gorgeous, secluded North Fork farm. Guests have exclusive use of screen porch, fire pit, bbq and outdoor seating area. Jess is a private chef and yoga instructor, so be sure to inquire for services! Private hiking trails, fresh eggs, produce from garden, beach gear, Keurig, mini fridge, homemade granola, tea.

Feb 7 – 14

R5,891 ZAR 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

R9,680 ZAR per night

Loft in Southampton

4.89 out of 5 average rating, 145 reviews

Getaway cottage privet and quiet

Cottage is on the property with the owner but it is completely separate from our own home. We are in a lovely quiet neighborhood. We are friendly with animals we have our own dog as well. 5 Minute drive to the bay and 10-minute drive to the ocean. Baby crib can be additionally installed. Pool is shared with my family on property

Dec 3 – 10

R7,304 ZAR 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

R14,837 ZAR per night

Home in Southampton

4.95 out of 5 average rating, 132 reviews

Waterview, PoolOpenNow! DogsFree+Kayaks+PingPong

May 26 – Jun 2

R16,502 ZAR per night

Home in Sag Harbor

4.89 out of 5 average rating, 166 reviews

Kiddo Approved! Heated Pool/Hotub Renovated Home

Sep 24 – Oct 1

R19,134 ZAR 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

R8,053 ZAR per night

Home in Cutchogue

4.94 out of 5 average rating, 50 reviews

Nassau Point, North Fork Home w/ Pool

Feb 4 – 11

R6,998 ZAR per night

Home in Mattituck

4.9 out of 5 average rating, 10 reviews

NorthFork FarmHouse, Amazing Pool, Beach,Vineyards

Dec 13 – 20

R17,280 ZAR per night

Home in Southampton

5.0 out of 5 average rating, 23 reviews

Renovated Southampton Home+Pool

Feb 3 – 10

R6,710 ZAR per night

Home in Southampton

5.0 out of 5 average rating, 58 reviews

Dream home in SH with Heated Pool OPEN from May 4

Feb 15 – 22

R9,684 ZAR per night

Condo rentals with a pool

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

R8,333 ZAR 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

R10,075 ZAR per night

Condo in Old Saybrook

4.91 out of 5 average rating, 57 reviews

Seashore getaway - CT shoreline

Dec 23 – 30

R3,543 ZAR per night

Condo in Greenport

4.81 out of 5 average rating, 88 reviews

Beautiful condo on Long Islands Northfolk

Feb 28 – Mar 7

R11,181 ZAR per night

Condo in Shelter Island Heights

5.0 out of 5 average rating, 5 reviews

Peaceful and Relaxing Waterfront.

Feb 14 – 21

R10,601 ZAR 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

R10,318 ZAR per night

Condo in Hampton Bays

4.97 out of 5 average rating, 33 reviews

A Unique Piece of Paradise, Water Front pool

Nov 3 – 10

R8,473 ZAR per night

Condo in Greenport

4.83 out of 5 average rating, 30 reviews

Two Bedroom Lawn Side 1st Floor Condo!

Dec 10 – 17

R7,184 ZAR 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

Nov 16 – 23

R18,809 ZAR per night

Home in Remsenburg

4.95 out of 5 average rating, 64 reviews

Experience a Quiet Hamptons Getaway

Apr 4 – 11

R11,088 ZAR 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

R13,783 ZAR 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

R13,864 ZAR 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

R10,638 ZAR 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

R8,868 ZAR 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
R2,402 ZAR before taxes and fees

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