Holiday rentals in Shelter Island

4.91 out of 5 average rating, 89 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

Cottage in Shelter Island

4.96 out of 5 average rating, 48 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.

4.9 out of 5 average rating, 123 reviews

Hay Beach Family Home: Fire Pit, Playroom, Yard

Two blocks from Hay Beach, this family-and-dog-friendly 3BR sleeps 6 in a quiet Shelter Island neighborhood. Fenced yard, fire pit, playroom, crib, toddler toys, beach gear, and bikes included. The home was built for families: open living area with wood-burning fireplace, full kitchen, 2 full baths, basement playroom, and workout space. Outside: fully fenced yard, fire pit, sun loungers, propane grill, Big Green Egg. Winter stays: $0 cleaning fee Nov–Mar.

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, 69 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.

Guest house in Shelter Island

An expansive saltwater pool is featured in the foreground, with clear blue water reflecting the sky. Surrounding foliage includes lush green trees, providing a natural setting. The tranquil bay is visible in the distance, enhancing the property's serene atmosphere.

4.99 out of 5 average rating, 72 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!

4.88 out of 5 average rating, 67 reviews

Secluded and Sheltered

Permit No. 2025-L-0060; Exemption #2025-0259 2-day minimum stay. Renovated (2015) 4 bedroom, 2.5 bath Gambrel home, Silver Beach. Open kitchen & updated baths & appliances, 18 x 36 pool (Memorial Day - Labor Day only), CAC; white-painted, wood-flooring. Charcoal grill. Dog friendly home. Working fireplace, large wooded yard. 1.6 acres, walk to private beach with sunsets. Best of Hamptons without the hassle!

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.

4.94 out of 5 average rating, 49 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.

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

Home in Shelter Island Heights

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, 50 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.

Home in Shelter Island Heights

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, 18 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.

Flat in Shelter Island Heights

4.9 out of 5 average rating, 260 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

Cottage in Shelter Island

A traditional New England-style house features a front porch supported by white columns. Two white chairs and a small table are arranged on the porch, complemented by a dark front door. Large windows allow natural light to fill the space, surrounded by green landscaped areas.

4.97 out of 5 average rating, 116 reviews

3 Bedroom Cottage Gem

Traditional Shelter Island house, located in the heart of central village. This 3bedrooms/2 bathrooms house is really quiet, convenient for tennis players with courts cross the street, 4bikes to borrow. This house is close to restaurants and is close to the beach as well...

Popular amenities for Shelter Island holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Shelter Island

5 out of 5 average rating, 5 reviews

Shelter Island 4 BR w Pool & Private Beach Access

4.93 out of 5 average rating, 82 reviews

Family Friendly Island Home

The exterior of a mid-century home is showcased, featuring dark wooden siding and a gently sloping roof. A pathway of square stones leads to the entrance, bordered by lush green shrubs and vibrant flowering plants. The surrounding yard is spacious and well-maintained.

4.93 out of 5 average rating, 43 reviews

Light, spacious 3bdr home steps to Wades Beach

Guest house in Shelter Island

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

A clear blue pool reflects sunlight, surrounded by a spacious deck. A stylish outdoor seating area with a cozy, round lounge chair is positioned beside the pool, offering a perfect spot for relaxation. Large windows of the house overlook the tranquil setting.

4.93 out of 5 average rating, 16 reviews

Waterfront Haven

A wooden deck features a spacious seating area with sun loungers, complemented by a table under a striped awning. Surrounding greenery enhances the serene environment, and a sparkling gunite pool is visible in the background, inviting relaxation.

4.96 out of 5 average rating, 69 reviews

Shelter Island home with pool

4.92 out of 5 average rating, 12 reviews

Captain Don’s Paradise