House holiday rentals in Shelter Island

4.91 out of 5 average rating, 141 reviews

Serene w/ large pool ~1 block to waterfront dining

Serene, chic Hamptons oasis! Located 1 block to waterfront dining + 8 mins to Main St. A perfect escape for any time of year! During summer, swim all day + walk 1 block to waterfront dining for dinner, drinks, coffee on the sea! During fall/winter, enjoy the firepit, indoor wood burning fireplace, 80' streaming TV + large fully stocked Chef's kitchen! The home is nestled in nature and serenity, perched back on a large piece of private property. Perfect for a serene escape to relax and unwind!

LocationFamilyLayout

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.

LocationFamilyComfort

5.0 out of 5 average rating, 11 reviews

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

Escape to our stylish mid-century modern retreat on Shelter Island. A 1 minute walk to stunning Crab Creek and a private neighborhood association beach, our home boasts 3 bedrooms, 2.5 baths and an outdoor shower, and sits on nearly an acre of secluded land. The backyard is a private oasis with towering trees, a bamboo forest and a large pool surrounded by beautiful landscaping. Enjoy an indoor fireplace in winter, an outdoor fireplace and grill in summer, or a beach bonfire under the stars.

FamilyLocationBeach

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.

FamilyValueHospitality

4.91 out of 5 average rating, 201 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.

ValueFamilyAir conditioning

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

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**

LocationFamilyKitchen

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.

ValueFamilyComfort

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!

FamilyValueAccuracy

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!

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.

FamilyLocationBeach

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

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.

FamilyValueCheckout

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.

LocationValueCleanliness

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, 22 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.

FamilyLocationBackyard

Popular amenities for Shelter Island house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

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.

4.89 out of 5 average rating, 117 reviews

Modern East Hampton Home w/ Heated Saltwater Pool

LocationFamilyHospitality

4.95 out of 5 average rating, 203 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

ValueFamilyAir conditioning

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

LocationFamilyCleanliness

4.93 out of 5 average rating, 107 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

LocationFamilyPets

A spacious backyard features a heated swimming pool surrounded by a sun deck, adorned with loungers. Lush greenery and trees provide a natural backdrop to the inviting setting, while a charming house is visible in the distance.

4.89 out of 5 average rating, 133 reviews

4 BD w/ Heated Pool in E Hampton, Fully Furnished

FamilyValueLong stay

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.

4.93 out of 5 average rating, 138 reviews

Private & Pristine with Pool and Kid’s Playard

LocationFamilyPool

4.96 out of 5 average rating, 184 reviews

Home in Mastic

Family Retreat with Heated Pool, Hot Tub, Sauna.

ValueLocationLaundry

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

FamilyLocationCleanliness

Weekly house rentals

4.92 out of 5 average rating, 97 reviews

Surf Scoter Cottage Shelter Island

FamilyValueView

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, 54 reviews

Silver Beach, 3 Bedroom cottage w/ pool

LocationFamilyCondition

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

LocationFamilyComfort

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

LocationValueLayout

4.88 out of 5 average rating, 16 reviews

4 Bedroom Sag Harbor Home w/ Pool & Tennis Access

LocationFamilyQuiet

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

ValueFamilyCleanliness

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.

4.91 out of 5 average rating, 74 reviews

Walk to Beach and Greenport Village, Two King Beds

LocationFamilyComfort

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.

4.92 out of 5 average rating, 12 reviews

Sag Harbor Village Waterfront Cottage

LocationFamilyTV

Private house rentals

4.95 out of 5 average rating, 21 reviews

Home in Southampton

Brand New Sun Filled Home

FamilyLocationHospitality

4.85 out of 5 average rating, 53 reviews

Historic Home + Private Waterfront Access

FamilyValueQuiet

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, 33 reviews

Pennington House

FamilyLocationComfort

4.89 out of 5 average rating, 18 reviews

Bayview house with salt water pool & private chef

LocationFamilyTV

4.94 out of 5 average rating, 50 reviews

A private swimming pool reflects clear blue skies, surrounded by lounge chairs and umbrellas. Lush greenery frames the scene, while a wooden deck leads to the main house, which features a modern architectural design. A swing set adds an element of leisure to the serene outdoor space.

Home in East Hampton

¤¤¤ Wonderful retreat on 4 acres with pool ¤¤¤

FamilyLocationPets

4.8 out of 5 average rating, 44 reviews

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.

Home in North Fork

Stylish Getaway in Greenport

LocationFamilyBackyard

5.0 out of 5 average rating, 45 reviews

A spacious backyard is featured, with a circular stone fire pit surrounded by several colorful Adirondack chairs. Lush green grass extends towards a charming white house in the background, bordered by trees under a clear blue sky.

Home in Southold

Private Waterfront Access + Hot Tub + Scenic Yard

ValueLocationAccess