Vacation rentals in Shelter Island

4.91 out of 5 average rating, 91 reviews

Surf Scoter Cottage Shelter Island

New heated gunnite Pool & pea gravel driveway. 4BR renovated mid-century ranch with a breezy nautical theme. Central A/C. Giant back deck: Propane & Charcoal BBQ, Jacuzzi, Hammock & glorious Outdoor Shower. Private front & back yards. Fab mirrored bar, cozy kitchen, double-sink master bath+full 2nd bath. Impressive vinyl collect & 4 speaker Bluetooth stereo, Piano, chill basement media room + ping pong & foosball ! washer/dryer. 4 bikes, beach chairs, cooler & umbrella. $100 /dog sorry no cats

5 out of 5 average rating, 22 reviews

Home in Greenport

Beach Block Hideaway

100% Walking Score 4 blocks away from Village 1 block away from Beach. 4 blocks away from Shelter Island Ferry. 4 blocks from Hampton Jitney & LIRR Newly renovated home! Located right in Greenport Village providing walking distance to all the restaurants, bars, shopping, coffee shops. Down block from beach restaurants and dining, the beach, nightlife, and public transport. Incredible location, safe, cozy. 2 King Size(Bedrooms) 2 Pull-out Full-size (Porch) 1 Couch (Living Room) 1 Bathroom

An expansive outdoor area features a heated pool and hot tub, surrounded by lush greenery and tall trees. Lounge chairs with umbrellas are positioned nearby, set against a backdrop of vibrant grass and shaded by mature trees, creating a serene space for relaxation.

4.91 out of 5 average rating, 33 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**

Cottage in Shelter Island

4.96 out of 5 average rating, 50 reviews

Cozy Shelter Island 2 Bedroom 1 Bath Cottage

This cozy cottage is perfect place to relax and unwind. Located in the center of the island about a mile from the beach and nature preserve. Sleeps up to 9 people - with queen size aero bed provided. Linens, dishes, utensils etc. included. Fridge has icemaker and filtered water feature. Outdoor covered dining area with table and 8 chairs. 2 person swing, BBQ & outdoor shower. 2/3 acre property. Relax with the whole family at this peaceful place to stay.

A spacious house is framed by lush landscaping, featuring a large pool in the foreground. Sun loungers and patio umbrellas are arranged around the pool, along with a pink float. The exterior showcases a combination of shingle siding and solar panels under a clear blue sky.

4.94 out of 5 average rating, 72 reviews

Beautiful beach home with pool & water views!

Perfectly situated just past the Island Boatyard and Salt in a blissful neighborhood surrounded by water on 3 sides. 4 town landings and beach access right across the street. Newly renovated gourmet kitchen with large island and beautiful quartz counters. Back deck offers full outdoor dining space with propane Weber grill, wicker seating area with beautiful propane Firepit for hours of evening enjoyment and chaise lounges by the pool.

Guesthouse in Shelter Island Heights

A serene saltwater pool is framed by lush greenery and blooming flowers, enhancing the outdoor space. A hot tub is positioned alongside, inviting relaxation. The guest house is visible in the background, surrounded by trees and well-maintained landscaping.

4.99 out of 5 average rating, 73 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, 63 reviews

Cottage in North Fork

3 Min Walk to Beach| 1 Mile to Town | Fam-Friendly

<b>The Greenport Beach Cottage</b> • Bright & updated 800 sq ft coastal cottage • 3 minute walk to beach, 4 minute drive to town • Sleeps up to 5 guests • Family-Friendly Amenities • Backyard with 2 fire pits, charcoal & gas grill, outdoor shower • Garage with 4 beach cruiser bikes, Foosball table & small gym area Book your coastal getaway now- only a few summer weekends remaining! IG: @thegreenportbeachcottage

4.94 out of 5 average rating, 51 reviews

The exterior of a two-story house is depicted, featuring a light-colored facade with a welcoming front porch. Clear blue skies and greenery surround the property, while the lawn is well-maintained, offering a spacious area in front of the house.

Home in Shelter Island

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.

A charming three-bedroom home features light green siding and a covered porch. A stone pathway leads through a lush, well-maintained yard, flanked by greenery. The surrounding trees provide shade, contributing to a serene outdoor setting.

5 out of 5 average rating, 9 reviews

Peaceful Bright Country House

Centrally located bright, and spacious three-bedroom home 10-minute walk to Crescent Beach and town for shopping and cafes. Nice backyard for barbecue Enjoy a peaceful stay at this quiet and colorful country home on beautiful Shelter Island. 1-minute walk to Léon 1909 restaurant and the Tuck Shop for ice cream. 2-minute drive to historic Goat Hill public golf course. NO PETS PLEASE

A modern mid-century ranch house is set against a clear blue sky. Lush green grass surrounds the home, complemented by neatly trimmed shrubs. A paved pathway leads to the entrance, while trees provide a natural backdrop, enhancing the privacy of the property.

4.9 out of 5 average rating, 51 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.

A spacious living area features a brick fireplace with a mounted television above. Light-colored sofas are arranged around a wooden coffee table. Natural light enters through large windows, with a dining area visible in the background. Decorative lanterns adorn a rustic table.

5 out of 5 average rating, 20 reviews

Laid Back Relaxation

Kick back and relax in this calm, stylish space. Nice newly updated home on a quiet street within walking distance to beaches, restaurants and a golf course. Great location near Shelter Island heights town, Crescent beach and Sunset beach. The location provides both privacy and relaxation at home with just a short walk or ride to popular Shelter Island spots.

Superhost

A round wooden dining table is surrounded by four metal chairs. Natural light enters through two large windows, with framed black-and-white photographs arranged on the wall beside them. A decorative centerpiece is placed on the table, offering a rustic touch to the space.

Apartment in Shelter Island Heights

4.9 out of 5 average rating, 263 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

Popular amenities for Shelter Island vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Other great vacation rentals in Shelter Island

4.93 out of 5 average rating, 83 reviews

Family Friendly Island Home

Cottage in Shelter Island Heights

A bright living area features large windows that overlook a serene waterfront. Two modern white sofas are positioned around a glass coffee table, with a small lamp on each side. A wood-burning fireplace and built-in shelving add to the contemporary design.

4.93 out of 5 average rating, 27 reviews

Waterfront Getaway on Shelter Island

A spacious wooden deck is featured, equipped with a dining table and lounge chairs. The entrance to the house is visible, illuminated by soft outdoor lights. Surrounding greenery adds a natural element, creating a welcoming outdoor space for relaxation.

Bungalow in Shelter Island Heights

4.94 out of 5 average rating, 16 reviews

Two bedroom bungalow

Guesthouse in Shelter Island Heights

A spacious studio features a cozy queen bed with a light grey duvet and matching pillows, complemented by two ceiling fans. A comfortable seating arrangement includes a modern sofa and armchair. Large windows provide ample natural light, and a soft area rug enhances the warm aesthetic.

4.92 out of 5 average rating, 12 reviews

Stylish Studio Suite on Shelter Island

5 out of 5 average rating, 23 reviews

Home in Shelter Island

Shelter Island Retreat, 5 bdrms near everything!

Home in Shelter Island

4.92 out of 5 average rating, 12 reviews

Captain Don’s Paradise

Apartment in Shelter Island Heights

The living area features large glass doors that open to a view of trees and distant water. A light grey rug anchors two chairs and a sectional sofa, while a small circular coffee table holds a chess set. A television is mounted on the wall.

5 out of 5 average rating, 17 reviews

Modern Waterview Apartment in Silver Beach

A serene poolside scene features a clear blue saltwater pool alongside a comfortable lounge area. An umbrella provides shade over the sunbed, while a rustic outdoor seating arrangement sits nearby, surrounded by lush trees and well-maintained landscaping.