Holiday houses in Shelter Island

4.98 out of 5 average rating, 85 reviews

Modern, spacious SI home with pool

Built in 2015, this airy 4-bedroom house sits on a private acre near Hay Beach and comes with a heated 16x38 gunite pool, well-equipped kitchen, gas grill and modern amenities. Contemporary furniture, uncluttered space; home office with a wired internet connection. Pool is open between 5/20/25 and 9/29/2025. Pricing inclusive of weekly cleaning, pool, yard, and garbage collection services as well as utilities. *Propane for pool heating charged separately for stays a week or longer*

4.88 out of 5 average rating, 26 reviews

Newly Renovated w/ Pool, Hot tub & Fireplace

Shelter Island Rental License #: 2025-L-0056 !!!PLEASE DO NOT PUT IN A BOOKING REQUEST UNTIL WE HAVE HAD A CONVERSATION VIA THIS SITE. THANK YOU!!!! Great for fall and winter! Perfect for families! 4 Adults Max. Newly renovated, light filled home! Heated pool and hot tub in summer in a private tree-filled yard. Fireplace and great sledding in the colder months. Mid-century modern style; close to Shelter Island Heights and beaches. **POOL & HOT TUB CLOSED MID OCTOBER UNTIL MAY**

4.96 out of 5 average rating, 164 reviews

Shelter island retreat

Two bedroom on the top floor of a house on Shelter Island on secluded one-acre. fire pit, wood-burning fireplace, layered decks, stainless steel kitchen, five minutes to beach. close to the south ferry .outdoor sauna and hot tub. Own entrance very private. owner lives on property as well in very separate space. 19W-0009 Own entrance very private. owner lives on premise as well in very separate space.has cat that lives in studio with owner 19W-0009 Long term rental also Available

Guest suite in North Fork

4.91 out of 5 average rating, 315 reviews

The Greenport Suite—private entry + near the beach

Welcome to The Greenport Suite! With its separate entrance, secluded outdoor patio space and ideal location, this newly-redesigned private suite in our contemporary Village home is perfect for enjoying a North Fork getaway. We are located just a few short blocks from bay beaches, the harbor, and public transport, while the area's celebrated wineries are a short drive or bike ride away. Come see why Forbes named Greenport one of the 11 prettiest villages in the United States!

4.94 out of 5 average rating, 187 reviews

Home in North Fork

Harbor Heights

Newly renovated 2-Family Home! Located right in Greenport Village providing walking distance to all the restaurants, bars, shopping, coffee shops, and Shelter Island Ferry, Long Island Railroad (LIRR), and Hampton Jitney. My place is close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place because of Location!. My place is good for couples, solo adventurers, business travelers, families (with kids).

5 out of 5 average rating, 13 reviews

Home in North Fork

Kayaks ~ Bikes ~ Boards ~ 6mins> Greenport ~ 55"TV

★ "Beautiful hidden home on the water… enjoy the North Fork summer in style." Private beachfront property with 2 homes & views of Gardiner’s bay. ☞ Bikes + kayaks + paddle boards ☞ Wrap around balcony w/ seating ☞ Fully equipped + stocked kitchen ☞ Deck w/ lounging + water views ☞ Dedicated workspace + printer ☞ Master w/ king + bathroom ☞ 55” Smart TV + Xbox ☞ Indoor gas fireplace 6 mins → DT Greenport (cafes, dining, shopping) 13 mins → Orient Beach State Park ⛱

Guesthouse in Shelter Island

5 out of 5 average rating, 64 reviews

Bayfront 1BR/2BR detached guesthouse with pool

Perfect relaxing getaway for a couple or family. Bayfront 1BR/2BR fully detached guest house with gorgeous morning views. Property has saltwater pool + hot tub (open May -October) and bay access via private dock. Central to both north & south forks (wineries + Hamptons or Montauk just short drive away). Down the road from famous Shelter Island Sunset Beach + golf course. Come explore the beauty of the Hamptons without the stress!

5 out of 5 average rating, 26 reviews

Hamptons - Shelter Island Farmhouse

Kid friendly! Perfect two family split! Come enjoy our island retreat. Relax with the whole family at this peaceful pad. You will be 2 min on bike from Wades Beach. You can also walk to the best BBQ/seafood in Shelter, Commander Codys. Features a large open kitchen/dining room plus also a spacious living room. 4 bedrooms with new mattresses, huge outdoor patio for family BBQs. No dogs please.

Superhost

4.9 out of 5 average rating, 116 reviews

Hay Beach Getaway!

Welcome to our family-friendly oasis just two blocks from beautiful beaches! Our house offers an open space living area, an expansive yard, fire pits, and a basement with a playroom and workout area. Enjoy our quiet neighborhood. We provide kid-friendly toys, beach gear, bicycles, and more. Sleeps six, with additional options available for larger parties. Cleaning fees for winter stays are 0$.

Home in Shelter Island Heights

4.95 out of 5 average rating, 40 reviews

Silver Beach, 3 Bedroom cottage w/ pool

Enjoy summer on Shelter Island in this 3 bedroom, 2 bathroom, freshly painted and well equipped MCM ranch house on 3/4 of an acre. Located at the end of a private road, it's in walking distance to Shell Beach, town landings and a beautiful sunset viewing spot. Brand new, heated, inground pool w/ color changing light, central air, deck, fire pit and BBQ make this a great vacation home.

Guest suite in North Fork

4.88 out of 5 average rating, 665 reviews

Walk to Vineyards, Beaches, Farms & Town

Private bungalow with a separate entrance in a historical tudor home. Spacious bedroom with king-sized bed, kitchenette and bathroom. Two bikes, cable TV, internet, AC, beach towels, parking, snacks, coffee and water all provided. Walking distance to the beach, restaurants, shops, vineyards, grocery, farms and fish market. Jitney stop is one block away!

Apartment in Shelter Island Heights

4.91 out of 5 average rating, 247 reviews

Squire Chase House

Wide open loft like space in the heart of the Heights walking distance to North ferry and Marie Eiffel market Many antiques including 1930s leather club chairs and a wonderful 1850 Swedish gustavian sofa in the living room many original pieces of art work Note :the bath tub in the master bedroom is for decoration only Shelter Island license B Zone

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Other great holiday rentals in Shelter Island

5 out of 5 average rating, 11 reviews

Waterfront Estate on Shelter Island. 100 Ft Dock

TrevorRating, 5 stars11 months ago

Had a wonderful stay at Edward and Tracey’s place! Incredible lot and view of the water. Dock has a floating portion to ease access during low/high tide. Very private, nice quiet and secluded location. But also quite close to IGA (grocery), activities, and other local points of interest. House has lots of charm and had everything we needed for a multi-week stay. A great home base for your shelter island adventures! Thank you Edward and Tracey for your amazing hospitality! Would not hesitate to return to this special place.

5 out of 5 average rating, 13 reviews

Waterfront Treehouse with Pool as seen on HBO

Susan BRating, 5 stars3 weeks ago

This very unique home is in the most beautiful spot on Shelter Island. Paradise. An incredible view of the creek on one side, a gorgeous pool and garden on the other. The house is so pretty, spacious and well-equipped. Hosts are extremely responsive and accommodating. I would definitely go back.

Home in Shelter Island Heights

5 out of 5 average rating, 10 reviews

Laid Back Relaxation

SallieRating, 5 stars3 weeks ago

We really enjoyed Jared’s property. The light-filled living and dining room were spacious and comfortable, and the kitchen was modern and well-equipped. We would stay here again!

5 out of 5 average rating, 5 reviews

Designer Renovated Farmhouse with Pool

FrancisRating, 5 stars1 month ago

We really needed the solitude and my daughter and I had a fantastic rest. What a great place to hibernate in the winter! Great comfortable beds, well stocked kitchen In a beautiful space. It is a bird sanctuary with nice walks and brilliant cycling.

5 out of 5 average rating, 3 reviews

New vacation house on the island(new pool)

JamesRating, 5 stars9 months ago

Iwona was a terrific host. The home is immaculately maintained, with high ceilings and large windows looking over beautiful green space. It is a calming environment, both indoors and out. The location is convenient to the town center, a nature preserve, beaches, restaurants, and the north and south ferries. Based on our experience, we recommend highly!

5 out of 5 average rating, 7 reviews

6-acre Hidden Estate for 10 w/FP, Pool, Chef's Kit

JaneRating, 5 stars2 weeks ago

Several of my family members stayed at Christine's house while on Shelter Island for a family wedding. The main house and cottage were both so beautiful and so comfortable and cozy. The grounds were positiviely idyllic including the tucked away, inviting pool. It truly felt like it could be our family's house. We all fell in love. The beds were comfortable with crisp white linens. When we weren't outside, the kitchen was a constant gathering place as was the sunroom and the dining room. I can't say anything about the TVs since we didn't turn one on once. Didn't even think about it - were having too much fun being together. Internet was great! Before arrival, Christian was a constant source of communication, making sure we were all set. Pay attention to his succinct instructions of how to get to the house. They are spot on. Kim, the manager, was there to greet us and let us in and answer any questions. She was so helpful. Going to SI? Stay at Christine's! You'll be glad you did!