House vacation rentals in Shelter Island

4.91 out of 5 average rating, 142 reviews

Home in Springs

Serene + private ~ 8 mins to Main Street + beaches

The perfect Hamptons getaway! Near all of the best attractions. Enjoy this chic, serene home surrounded by the beauty of Hamptons nature + birds' chirping, deer sauntering. Cozy up to the wood burning fireplace, 80' TV + Chef's kitchen. Spark up the BBQ + firepit under the starry sky! Enjoy the bucolic views from every room. Here, you will be 8 minutes to Main St of East Hampton + Amagansett for endless dining + shopping options! Also 5-10 minutes to gorgeous beaches (great any time of year!).

FamilyLocationAccuracy

4.97 out of 5 average rating, 101 reviews

The exterior of a modern two-story home features a sleek white facade with large windows allowing for ample natural light. A covered porch provides a welcoming entrance, alongside neatly arranged greenery and stone pathway leading to the front door.

Home in Southampton

Southampton Village Newly Built Gem

Enjoy a stylish experience at this 3765+ sq ft., just built, SH Village gem! Beautiful and bright spacious home with 5 well appointed bedrooms, multiple custom closets and 5.5 baths (4 ensuite). Luxurious lighting fixtures throughout the home. Living room fireplace, vaulted wooden beam kitchen ceiling with formal dining for 10 plus. Gunite pool and spa, with multiple outdoor seating areas. Expansive media room with 75 inch TV and room length comfy cloud sofa. Two sets of washers and dryers.

FamilyLocationCheck-in

4.93 out of 5 average rating, 136 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.

ValueLocationHeating

4.96 out of 5 average rating, 186 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

LocationValueIndoor spaces

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, 139 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

ValueFamilyHiking

4.9 out of 5 average rating, 130 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.

FamilyValueCleanliness

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.

FamilyValueKitchen

4.95 out of 5 average rating, 395 reviews

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.

Home in Greenport

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.

LocationFamilyGetting around

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.

ValueLocationAccuracy

4.93 out of 5 average rating, 55 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.

FamilyValueLayout

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, 324 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.

FamilyValueParks

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.

5.0 out of 5 average rating, 23 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.

LocationFamilyKitchen

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, 205 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

LocationValueAccuracy

4.94 out of 5 average rating, 185 reviews

Home in East Hampton

1800 Historical EH Home, 1 Mile to Town!

LocationFamilyWalkability

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

ValueFamilyQuiet

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.

4.97 out of 5 average rating, 218 reviews

Private Oasis W/Stunning Vinyard and Pool Views

LocationFamilyAmenities

A cozy bedroom featuring a spacious bed dressed in soft linens is positioned against a light-colored wall. Natural light filters through two windows, casting gentle shadows on the warm wooden floor. A ceiling fan hangs overhead, and a mirror and chair add functional elements to the space.

4.96 out of 5 average rating, 221 reviews

Secluded Farmhouse - Studio Apartment Style Unit

LocationFamilyCheck-in

4.93 out of 5 average rating, 109 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

ValueFamilyBeach

4.93 out of 5 average rating, 100 reviews

A serene backyard features a large swimming pool surrounded by lush green grass. Lounge chairs are positioned around the water, accompanied by shaded umbrellas. Mature trees and landscaping provide a natural backdrop, enhancing the privacy of the space.

Home in Shinnecock Hills

5BR, Luxury Home, Close to Beach,Town, PerfectYard

LocationFamilyQuiet

4.78 out of 5 average rating, 146 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

ValueFamilyOutdoor spaces

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!

FamilyLocationKitchen

5.0 out of 5 average rating, 11 reviews

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

LocationFamilyBeach

4.92 out of 5 average rating, 98 reviews

Surf Scoter Cottage Shelter Island

ValueLocationPool

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

ValueFamilyTV

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

FamilyLocationWalkability

4.86 out of 5 average rating, 29 reviews

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

LocationFamilyAir conditioning

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

LocationFamilyPool

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.

4.89 out of 5 average rating, 44 reviews

North Fork Sound Front Home with Pool

LocationFamilyNearby

Private house rentals

A weathered wooden sign is attached to a large tree, directing visitors towards the beach. The sign is marked with the words 'TO THE BEACH' and is surrounded by a grassy area with additional trees in the background, offering a sense of calm and connection to nature.

4.96 out of 5 average rating, 69 reviews

The North Star: Greenport Waterview Beach Getaway

FamilyLocationDecor

A serene waterfront scene captures a vibrant sunset, showcasing a blend of orange, pink, and purple hues reflected on calm water. A wooden dock extends into the water, while silhouettes of people can be seen engaging at the water's edge.

4.85 out of 5 average rating, 13 reviews

Sag Harbor Village Waterfront Cottage

ValueLocationCondition

A well-lit living area features a large window and a glass door leading to the outdoor space. A modern fireplace is centered in the room, complemented by stylish furniture, including a curved sofa and a standing lamp. Art decor adds visual interest to the wall.

4.8 out of 5 average rating, 45 reviews

Stylish Getaway in Greenport

FamilyValueAmenities

4.85 out of 5 average rating, 53 reviews

Home in Springs

Historic Home + Private Waterfront Access

FamilyLocationGetting around

5.0 out of 5 average rating, 34 reviews

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.

Home in Greenport

Pennington House

FamilyLocationCheckout

4.97 out of 5 average rating, 60 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

FamilyLocationCleanliness

A living area features striped sofas and wooden furniture arranged for comfort. Shelves lined with books are visible in the background. Natural light fills the space through windows with shades, while a fireplace adds a classic touch to this welcoming space.

5.0 out of 5 average rating, 36 reviews

Charming Village Cottage

LocationValueComfort