House holiday rentals in Shelter Island

4.91 out of 5 average rating, 141 reviews

Home in Springs

Serene + private ~ 1 block to waterfront dining

Enjoy zen living at this serene, chic, Hamptons oasis! Ideally located 1 block to waterfront dining, 8 minutes to beaches + 9 minutes to Main St! Relax poolside w/ tons of greenery + nature views. Spark up the BBQ + firepit under the starry sky. Listen to the crickets + spot a deer on the property. Curl up to the wood burning fireplace, cook in your Chef's kitchen + stream on your 80' TV Enjoy coffee on the sea + dinner w the best sunsets just 1 block away. A perfect escape + place to unwind!

4.94 out of 5 average rating, 334 reviews

An enclosed outdoor living space features a wooden deck overlooking a heated pool. Furnished with a large round table and comfortable seating, natural light floods through the screens, creating an airy atmosphere. Elegant trees and lounge chairs visible outside enhance the serene environment.

Home in Bridgehampton

Amazing Home close to Everything -

Elegantly designed home featuring modern appliances, a seasonal heated pool, and situated just moments away from ocean beaches, Wolffer Vineyard, and the vibrant Bridgehampton/Sag Harbor villages. Set within meticulously curated landscaping, this property embodies perfection and meticulous attention to detail. Familiarize yourself with our disclosures, guidelines, and house rules. We maintain a strict no events, no parties, and no smoking policy — our home and property grounds are smoke-free.

4.93 out of 5 average rating, 134 reviews

A serene landscape features a heated saltwater pool bordered by lush greenery. Sun loungers are positioned around the pool under umbrellas, while a wooden fence with trees creates a peaceful backdrop, enhancing the outdoor relaxation space.

Home in Mattituck

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.

4.91 out of 5 average rating, 202 reviews

Barefoot Bliss | Quiet Family Retreat Heated Pool

Welcome to your Hamptons retreat. This bright single-level home sits in a quiet neighborhood just minutes from Main Street and the ocean. The private fenced yard overlooks a peaceful nature preserve and features a heated pool (June–Sept, heating available for a fee), hot tub, outdoor fireplace, and outdoor shower—perfect after a beach day. Family-friendly amenities include a sandbox, toys, crib, and highchair, with a separate safety fence surrounding the pool for added peace of mind.

4.96 out of 5 average rating, 184 reviews

Home in Mastic

Family Retreat with Heated Pool, Hot Tub, Sauna.

🛏 6 Bedrooms, 9 beds & 3 Full Baths 🏊‍♂️ Heated Pool & Relaxing Hot Tub 4-person Sauna 🏀 Half Basketball Court & 🏐 Volleyball Area 🏌️‍♂️ Private Golf Putting Green 🔥 Cozy Firepit & Outdoor Lounge Area 🛝 Swing Set & Kid-Friendly Yard 🍽 Fully Stocked Kitchen & Spacious Dining 🌐 High-Speed Wi-Fi & Smart TVs 10 min to Smith Point Beach & Boardwalk 15–20 min to Long Island Wine Country Nearby hiking at Wertheim Wildlife Refuge Short drive to Tanger Outlets & restaurants

Superhost

A bright living area features large windows that offer views of the nearby pond. Comfortable seating includes a white sofa, patterned chairs, and a coffee table, all arranged on a natural fiber rug. Light from the windows enhances the serene atmosphere.

4.86 out of 5 average rating, 138 reviews

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, and 10 mins to Bridgehampton. Location, location! And Views! - 3 Beds, 2.5 baths - 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. NOTE: Due to water leakage issues, the bath in pool house is not available

4.9 out of 5 average rating, 129 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.

The front exterior of the bungalow is showcased, featuring a wooden fence that provides privacy and a garden filled with hydrangeas. The house displays large windows that invite natural light, set against a backdrop of gravel and greenery.

4.97 out of 5 average rating, 295 reviews

The Greenport Bungalow

Sweet Modern Bungalow Walking Distance to Town Located in the historic town of Greenport Village - 8 min walk to the beach, center of town, Shelter Island Ferry and LIRR... A newly built sun filled 3 bedroom house with all the amenities you would need when renting a home. Enjoy the large and fenced in back yard after a fun day in this historic Long Island fishing village. Great restaurants, and even better locally produced wine and beer!

A cozy living area is highlighted by a chandelier, providing soft illumination. Two stylish chairs flank a round table, while a decorative sculpture and a vintage fireplace enhance the space. Large windows allow natural light to fill the room, offering views of the surrounding greenery.

4.9 out of 5 average rating, 117 reviews

The Cooper-Burke House

Many Main Street restaurants such as the American Hotel, Lulu's, Page 63, Wolffer Kitchen, Sen, Sag Pizza and Goldberg's, etc are a few minutes away. On Main Street one finds the Sag Harbor Cinema, The Bay Street Theater, Schiavoni's Market and Yoga Shanti. The house is a 12-minute walk to Haven's Beach. 1-minute around the corner from the house is Cavaniola's Wine, Cheese and Kitchen shops as well as the Sag Harbor Beverage store.

A bright living room features a comfortable gray sofa against a neutral wall, complemented by a light-colored rug with geometric patterns. A wooden coffee table sits in front, with a lounge chair nearby. Natural light enters through multiple windows, creating a spacious feel.

4.95 out of 5 average rating, 395 reviews

The Sandpiper

100% Walking Score 1 block away from Village 3 blocks away from Beach. 1 block away from Shelter Island Ferry. Around the corner from Hampton Jitney & LIRR Newly renovated 2-Family Home! This is for rental of 1st floor apartment (only) plus cabana, plus outdoor jacuzzi. Close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place! Incredible location, safe, cozy.

A two-story house features a light blue exterior beneath a gray shingled roof. Large windows allow natural light into the enclosed porch area, which is accentuated by landscaped flower beds with pink flowers and well-maintained green grass in the front yard.

5.0 out of 5 average rating, 101 reviews

Sag Harbor Village Gem

Sag Harbor Village Gem. 3 br, 2.5 ba., Enclosed Porch, Great Room with Fireplace, Charming Patio and Yard, Grill, Garage. Nicely landscaped property. House is immaculate. Spacious Master Bedroom with high ceiling. All bedrooms have beautiful dressers and TVs. Washer / Dryer. 10 minute drive to Ocean Beaches and 1 to 2 minute drive to Harbor Beach. 8 to 10 minute stroll to heart of Sag Harbor Village Main St.

A welcoming living area is illuminated by natural light from large windows. A comfortable gray sofa is complemented by light-colored armchairs and a coffee table adorned with books and decorative items. The neutral color palette is accentuated by indoor plants and a textured rug.

4.95 out of 5 average rating, 323 reviews

Sag Harbor Cottage, Walk to the Beach!

Renovated to perfection, this fully equipped fresh & modern beach cottage has an open-plan living room, dining room & kitchen, all with high ceilings, immaculate finishings, & a sunny lower level TV room. A broad mahogany deck with large outdoor shower & gas BBQ grill runs the full length of the house & overlooks a roomy lawn with great privacy, fire pit and mature landscaping.

Popular amenities for Shelter Island house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.95 out of 5 average rating, 204 reviews

A serene view of calm water featuring kayakers enjoying a sunny day. The distant shoreline is dotted with houses, creating a relaxed coastal atmosphere. Clear blue skies reflect on the water, enhancing the peaceful scene.

Home in Shinnecock Hills

Southamp Waterview, DogsFREE! Kayaks, Ping-Pong

4.93 out of 5 average rating, 108 reviews

A bright living area is furnished with a leather sofa and a dark coffee table, positioned on a textured rug. Natural light filters through large windows, illuminating the space. A staircase leads to an upper level, with wooden accents enhancing the modern design.

Home in Bridgehampton

Pool Central Private Bridgehampton Home

4.94 out of 5 average rating, 166 reviews

A well-maintained outdoor pool area is surrounded by a wooden deck and lush greenery. Lounge chairs are positioned along the pool, with a shaded area provided by a large tree. The clear blue water of the pool reflects the sunlight, inviting relaxation.

Home in Water Mill

Astounding Watermill 5 Bedroom home with Pool

4.78 out of 5 average rating, 145 reviews

The image captures a spacious outdoor area featuring a large heated pool with a fountain and surrounding stone patio. Nearby, lounge chairs are arranged for relaxation, while a generous lawn stretches in the background, accompanied by a well-designed home nestled among trees.

Home in East Hampton

Sprawling Hamptons Estate with Hot Tub & Amenities

Superhost

A modern home is set on a spacious green lawn, featuring a combination of wood and metal siding. Large windows allow natural light to fill the interior. A stone pathway leads to the entrance, framed by lush landscaping and trees, enhancing the outdoor tranquility.

Home in Springs

Modern East Hampton Home w/ Heated Saltwater Pool

4.89 out of 5 average rating, 117 reviews

4.97 out of 5 average rating, 218 reviews

A serene outdoor area showcases a saltwater pool with a spa, surrounded by well-maintained landscaping featuring vibrant yellow flowers. Lush green fields extend into the distance, framed by a clear sky with scattered clouds.

Home in North Fork

Private Oasis W/Stunning Vinyard and Pool Views

4.98 out of 5 average rating, 144 reviews

A crystal-clear swimming pool is surrounded by a landscaped garden featuring lush greenery and blooming flowers. Natural stone patio borders the pool, offering space for lounging and relaxation in a private setting nestled among trees.

Home in East Hampton

Explore the Water & Woods at a Relaxing Retreat

4.93 out of 5 average rating, 140 reviews

A spacious backyard is highlighted by a blue in-ground pool surrounded by lounge chairs. Red umbrellas provide shade, while a tall wooden fence adds privacy. Lush green grass complements the natural setting, and a rustic home is visible in the background among the trees.

Home in Springs

Private & Pristine with Pool and Kid’s Playard

Weekly house rentals

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.

4.95 out of 5 average rating, 79 reviews

Beautiful beach home with pool & water views!

4.93 out of 5 average rating, 54 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

5.0 out of 5 average rating, 11 reviews

Mid-Century Gem with Pool. Steps to Private Beach.

Superhost

A charming two-story house is surrounded by well-maintained greenery, showcasing a wraparound porch with multiple entry points. The exterior features wooden paneling, with large windows allowing natural light. Trees and shrubs frame the property, contributing to the serene setting.

Home in Shelter Island

Shelter Island Beach Retreat | Sleeps 10

4.86 out of 5 average rating, 29 reviews

4.92 out of 5 average rating, 98 reviews

Surf Scoter Cottage Shelter Island

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, 35 reviews

Newly Renovated w/ Pool, Hot tub & Fireplace

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.

4.91 out of 5 average rating, 56 reviews

Silver Beach, 3 Bedroom cottage w/ pool

A rectangular heated pool is surrounded by a well-maintained lawn and lush greenery. Trees and flowering bushes create a natural border, enhancing the tranquil outdoor setting. A house with a sloping roof is visible in the background, contributing to the serene environment.

4.98 out of 5 average rating, 94 reviews

Private Hay Beach Retreat with Heated Pool

Private house rentals

4.89 out of 5 average rating, 44 reviews

A spacious balcony extends along the side of the house, offering unobstructed views of the shimmering water. Weathered wooden benches provide seating, while the gentle waves can be observed lapping against the shore in the distance.

Home in North Fork

North Fork Sound Front Home with Pool

5.0 out of 5 average rating, 14 reviews

Sag Harbor Village 3 Bedroom Gem

4.97 out of 5 average rating, 59 reviews

A charming blue house is framed by lush green trees, with a welcoming front porch. Large windows invite natural light, while a white picket fence complements the tranquil outdoor setting. The spacious yard features vibrant grass, enhancing the peaceful atmosphere.

Home in Southold

The Saltbox: Outdoor Dining, Fire Pit, Soaking Tub

A modern two-story home features white siding and multiple windows that allow ample natural light. The entryway is framed by a small covered porch with a railing. A manicured lawn with stone pathways leads to the entrance, surrounded by low-lying shrubs.

5.0 out of 5 average rating, 34 reviews

Pennington House

4.88 out of 5 average rating, 24 reviews

A private pool area is shown with a clear blue swimming pool surrounded by four lounge chairs. A charming shed is situated in the background, framed by green trees and landscaped gardens.

Home in Southold

Stylish Beach Getaway: pool & walking location

The spacious deck is equipped with outdoor seating including a dining table under a large umbrella and lounging chairs. A grill is positioned near the railing. A lush green yard is visible beyond the deck, surrounded by trees and offering a serene outdoor setting.

5.0 out of 5 average rating, 46 reviews

Modern Farmhouse Oasis in GP Village

4.95 out of 5 average rating, 21 reviews

Home in Southampton

Brand New Sun Filled Home

An aerial view captures the serene landscape of a coastal area, showcasing a blend of residential homes and natural beauty. The water glistens under the sunlight, with sailboats dotted along the horizon, creating a peaceful atmosphere. Trees and green spaces provide a calming ambiance.