
Holiday 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.

Waterfront Autumn Escape in Wine Country: 2BR
Overlooking the Long Island Sound, this oceanfront condo is the ultimate escape. Bask in the sun on your private beach or unwind on the waterfront deck with breathtaking views Minutes from the town center, you’ll find local farms, award-winning wineries, gourmet restaurants & charming shops ⚓️ Explore Greenport: A historic seaport with coastal charm & rich culture 🏖 Premium Amenities – Waterfront deck, private balcony, grills, pool, private beach & parking ⛴ Ferry Access to Shelter Island & CT

Detached bungalow w/ private bath
Cozy, simple living, in separate guest house w/ use of amenities (shared with our family of 4) including sauna & hot tub. The bungalow/guesthouse features a Queen bed, its own private bathroom (shower), small kitchenette (countertop oven, Keurig coffee maker & small fridge) and loveseat for relaxing. There is a dedicated separate outdoor seating area for 2 guests. 2 Adult guests ONLY, no children due to size of guesthouse and proximity to the pool. Please NO pets allowed since owners have pets

Sag Harbor, Designer w large Pool (3 bed/2.5 bath)
Relax with friends / family at this home in a magical setting overlooking Lily pond Completely private but 5 mins to Sag Harbor downtown / restaurants / Havens beach, and 10 mins to Bridgehampton. Location, location! And Views! - 3 Beds and 2.5 baths + pool house - Pool house with twin sofa bed + full bath - 50ft heated Gunite pool (125/d extra to heat) - Outdoor deck overlooking pond - Amazing views! - Fire pit with Adirondack chairs Unique house to unwind while being close to the action

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

Modern farmhouse w/ pool, beach, horses and winery
A new, modernized farmhouse with a heated saltwater pool in the heart of North Fork. Nestled on an acre of lush, fully fenced yard, the home can easily accommodate up to 8 guests and all pets! Minutes away from Love Lane (Mattituck's charming downtown), Breakwater Beach (one of best beaches in North Fork), Mattituck train station and surrounding the award winning Bridge Lane Vineyards and picturesque Seabrook Horse Farm, this bucolic home offers the perfect setting for a North Fork getaway.

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.

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. Fresh eggs, seasonal veg from the garden, and meals (inquire!)

Sag Harbor Wonder, 3 bedroom 2 Bath & Heated 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. 10 minute drive to Wolffer & ocean beaches. 3 bedrooms, 2 modern bathrooms and heated pool with mature landscaping offers a relaxing escape. Please read the additional disclosures, guidelines, and rules. No events, no parties, no smoking – no exceptions!

Stunning 3 bed 2 bath home W Pool
Nestled on a serene an acre off a tranquil lane, this contemporary, designer-updated residence provides an idyllic Hamptons retreat. With 3 delightful bedrooms, 2 sleek bathrooms, and a seasonal heated pool amidst mature landscaping, you're promised a calming respite. We kindly ask that you familiarize yourself with the detailed disclosures, & guidelines. We maintain a strict policy against events, parties, and smoking. our home and property grouds are smoke-free.

Light-filled Sag Harbor village gem
Midcentury style in the heart of Sag Harbor Historic district. Soaring 20-foot floor-to-ceiling windows and skylights throughout offer the ideal indoor-outdoor experience for enjoying all seasons. Featured in Home & Garden, the house is situated on sprawling grounds, one of the largest lots in Sag Harbor. In the winter, enjoy the Scandinavian sauna and lounge in front of the fireplace. Gunite pool open May 25 to Sept 3.

Classic Southampton Village Home w/ Pool
Newly renovated Southampton village home with great light, offering the best of indoor-outdoor living. A beautiful backyard with a pool surrounded by lush privet hedges for privacy. Perfectly situated in the heart of the village, one block from restaurants, shopping, and one mile from the ocean beaches. Perfect with space to spread out, play or work remotely! Ask about special rates for long-term summer rental!

Astounding Watermill 5 Bedroom home with Pool
Situated off of a quiet lane on a half-acre of land, updated, modern residence offers a peaceful and quiet Hamptons getaway. 5 bedrooms / 3 modern bathrooms offers a relaxing escape. Large open kitchen leads out to the back garden, pool and indoor-outdoor eating areas. Please read the additional disclosures, guidelines, and rules. No events, no parties, no smoking – no exceptions!
Popular amenities for Greenport rentals with a pool
House rentals with a pool

Cozy and Updated w/ Fireplace

Amagansett Farmhouse Retreat - Stars Sea Fire

Walkable Designer Home in East Hampton Village!

Spectacular Southampton Retreat!

Stylish Beach Getaway: pool & walking location

Stylish+Cozy Hamptons Winter Getaway-5min to Beach

Chic East Hampton 7 Bedroom, 7 Bath, heated Pool

East Hampton Oasis - Pool and Hot Tub
Apartment rentals with a pool

Greenport Getaway at Cliffside Condos

Cliffside Resort Poolside Condo A204

Beautiful condo on Long Islands Northfork

2 BR Waterfront Autumn Escape in Wine Country

Waterfront Elevated Bungalow - Spectacular Views

Beautiful Waterview Condo on the North Fork of LI

Newly Renovated Modern Townhouse w/Pool & Tennis

A Unique Piece of Paradise, Water Front pool
Home rentals with a private pool

East Hampton Ranch with Access to Clearwater Private Beach

Explore the Water & Woods at a Relaxing Retreat
Enchanting Home with Large Decks and Heated Pool
Perfect Getaway at Sunny Modern Shampton LakeHouse
Saltbox with Separate Poolhouse in Northwest Woods
Quick stats about holiday rentals with a pool in Greenport

Total holiday rentals
Explore 20 holiday rentals in Greenport

Nightly prices starting at
Greenport holiday rentals start at £275 per night before taxes and fees

Verified guest reviews
Over 660 verified reviews to help you choose

Family-friendly holiday rentals
20 properties offer extra space & child-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
20 of Greenport holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Greenport rentals

4.9 Average rating
Greenport stays are highly rated by guests – averaging 4.9 out of 5!
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