Holiday rentals with a pool in Greenport

Quiet, Upscale Retreat by the Beach with NEW Pool

We're on a quiet, tree-lined street, a lovely bike ride or walk from a pebble beach, with crystal clear water and stunning sunsets. Our house is the ideal base to explore the North Fork, where bucolic farmland abuts magnificent beaches. We're 5 minutes by car or 15 by bike to the charming seaside villages of Greenport and Orient. Our house is fully stocked, newly renovated and the spacious backyard borders 10 acres of lovely forest preserve. No large groups of unrelated adults. Brand new pool!

Stylish+Modern Cape w/Saltwater Pool-5min to Beach

Stylish+Modern Cape Beach House nestled in Hampton Bays South of the highway, 5 min drive to beaches. Heated Saltwater Pool. 4 Bedrooms+Crib room & Office. 2 Bathrooms. Outdoor deck w/family dining+BBQ. Fully fenced tree-lined back yard w/ beautiful sunsets. Upstairs King bedroom w/ensuite bthrm + Twin bedroom directly off master. Main floor has another King bedroom+Twin bedroom, master bath, lounge+kitchen w/huge sit-around island. TV Den. Central AC. 15 min walk/ 2 min drive to shops+train.

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

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!)

Ultimate House with Heated Pool, Hot Tub and Sauna

Ultimate house with 4 Bds, 3 Baths, finished basement with entertainment area and gym. Minutes from the Hamptons and North Fork. Everything for your rest in any weather and season. Yamaha piano, Japanese massage chair, karaoke, drum set, electric guitars, ping pong, fossball and pool tables,board games. Fully landscaped backyard with flowering plants, outdoor lights. 2 BBQ areas, Gazebo with fireplace and projector. Easy access to beaches, restaurants, farms, vineyards and shopping.

PRIVATE BASEMENT APARTMENT WITH POOL IN SAG HARBOR

Beautiful basement apartment partially in-ground, with many windows and private entrance is located in Sag Harbor , 3 minutes from village and Heavens Bech by car or 15 minutes walking distance . The apartment has king size bed and comfortable sofa in the living room . In the kitchen you can find coffe maker , toaster , microwave, dishwasher, small fridge , hot plate for light cooking . Tv , WiFi , Airconditoining , access to pool from May till end of the September .

Waterview+Pool, FreeForDogs! Kayaks/PingPong/Bikes

Beachy casual feel-good home easily located at the entrance to The Hamptons. Lovely views of the Bay, Nightly Sunsets & birds! Launch our Kayaks at street's tiny beach flowing from Cold Spring Pond into Bay. Or cuddle by the fireplace and play our many available games. We provide soft sheets & towels for the showers and & beach...priding ourselves on your comfort! Our Private-Pool is heatable & plant-surrounded with Outdoor Shower.

Peaceful Retreat in Immaculate Architect’s House

This "like new" contemporary home features 4 bedrooms, 3.5 baths, open living spaces, soaring ceilings, abundant natural light, and a modern kitchen. Nestled in tranquil West Tiana Shores, minutes from bay & ocean beaches, and charming Hampton villages (Southampton, Westhampton, Quogue). The living room directly faces your private pool, cedar deck, and lush garden—a perfect getaway for vibrant summers and relaxing winters

Greenport Beach house Mini Resort Spa & Catering

Nestled steps from the beach, and all that Greenport and the North Fork has to offer, this exquisitely charming 3 bedroom 2 bathroom waterfront home is absolutely delightful.. You’ll love my place because of the views, the location, the people, the ambiance, the outdoors space, and the Saltwater pool.. My place is good for couples, solo adventurers, business travelers, families (with kids), groups, and furry friends (pets).