Family-friendly holiday rentals in Shelter Island

4.91 out of 5 average rating, 138 reviews

Home in Springs

Serene w/ large pool ~1 block to waterfront dining

Enjoy your serene, chic Hamptons oasis! Ideally located 1 block to waterfront dining + 8 mins. to Main St. + beaches! Stay in a tranquil home surrounded by nature + privacy. Swim in the pool, spark up the firepit + BBQ under the starry sky! Stream on the 80' TV + cook in your Chef's kitchen. Take a stroll 1 block to cafe for morning coffee on the sea snd dinner/cocktails watching the sun set over the harbor. Walk home in four minutes. Enjoy the peace + calmness right here in your own home!

FamilyIndoor spacesBeach

Guesthouse in Southampton

A charming outdoor area features a black cottage in the background, with large glass doors reflecting the surroundings. The deck is adorned with potted red geraniums and wooden seating. A hot tub is positioned adjacent to the cottage, emphasizing a tranquil retreat atmosphere.

4.97 out of 5 average rating, 119 reviews

5 Star Rated Private Cottage Southampton/Sag Hrbr

The Honeycomb Cottage is a little retreat located on a lush acre of evergreens in Southampton rated 5 Star by every guest that has stayed. One block to Peconic Bay Beach - perfect for a day in the sun. A cozy space with TV, WiFi and Sun Deck. Luxury soaps provided, amazing shower and crisp white linens. Exclusive use of the Hot Tub for Cottage guests. Easy parking and located 15 minutes drive to Sag Harbor or Southampton Village. Koi pond with waterfall will sooth the mind and spirit.

FamilyKitchenTV

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.

KitchenFamilyNearby

4.94 out of 5 average rating, 154 reviews

A wooden tray is centered on a neatly made bed, featuring a book and a coffee cup. The bed is dressed with a white quilt, and a softly textured pillow is placed against the headboard. A bedside lamp provides gentle illumination.

Guest suite in Southold

Comfortable Suite, a walk to the beach

Keep it simple at this spacious and peaceful home. Built in 2019, this home was specially designed for sustainable, green living; ground-source heating, and super insulation allow for minimal environmental impact and provide a quiet and comfortable stay. About a five minute walk to McCabe’s Beach. Very near to wineries, farms, and the quaint shops and bakeries of Southold and Greenport. Little Fish restaurant and oyster sales all down the street. Short drive from Sparkling Pointe vineyard.

FamilyIndoor spacesGetting around

4.95 out of 5 average rating, 153 reviews

A serene beach scene captures a golden sunset reflecting on calm waters. The sandy shore leads to gentle ripples, while distant land silhouettes frame the horizon. A tranquil ambiance is created as the sun descends, providing a peaceful setting for evening strolls.

Apartment in Southold

Bright, Southold Studio Apt near beach & town

Pied a terre on the North Fork, in the heart of Southold village. Gorgeous bay beach 5 minute walk, as are farmstands, supermarket, Historic Southold Village with quaint shops, Hampton Jitney & LIRR. Lots of light, new contemporary space featuring full bathroom with bathtub. Perfect for one, suitable for a couple for weekend getaway. Small kitchenette perfect for simple food prep, morning coffee/tea. Chickens on property, fresh pastured eggs in your kitchenette upon arrival!

FamilyKitchenWi-Fi

Guest suite in North Fork

A serene beach scene is depicted, showcasing soft white sand bordered by gentle waves. Tall grasses sway in the foreground, framing the clear blue water that extends to the horizon, providing a sense of calm and natural beauty.

4.93 out of 5 average rating, 120 reviews

Enjoy a relaxing getaway to the North Fork

One bedroom suite, with separate entrance in quiet Nassau Point; a peninsula, surrounded by beaches. Nassau Point is a great place to bike, walk and enjoy nature. Fully functioning WiFI for guests looking to extend their stay, while working from home. Fishermen's beach is a 5 minute walk Causeway beach is a 10 minute walk with parking. Point beach, 1.5 mile walk, a Southold Parking Permit required. You will find 20 wineries within 5 miles, just a short Uber ride away.

Indoor spacesFamilyValue

4.9 out of 5 average rating, 128 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.

KitchenFamilyBeach

4.92 out of 5 average rating, 106 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

Longer stay and reduced rate please email 169bridgehamptoncottage@gmail.com. NOTE* Rest assured, as always, even more so now, our housekeeper is aware to put in the extra tedious clean needed for a happy healthy stay! 7 minute drive to Hampton classic or less 20 min bike ride. Restaurants, studio 89 gym, on same rd. Ocean+bay 5-10 min drive. Bike to 1 ocean Yoga/winery. Halfway to Sag Harbor+Bridgehampton. There is pet fee.

FamilyIndoor spacesSleep quality

4.95 out of 5 average rating, 321 reviews

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.

Home in Sag Harbor

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.

KitchenIndoor spacesAir conditioning

4.96 out of 5 average rating, 212 reviews

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.

Home in North Fork

Secluded Farmhouse - Studio Apartment Style Unit

Private studio suite with separate entrance and full bath in a modern North Fork farmhouse on a peaceful farm property. Enjoy a screened porch, fire pit, and outdoor seating. Includes mini fridge, Keurig, tea, homemade granola, and seasonal eggs/produce. Attached to our home, so some light household noise is possible. Private chef + yoga services available.

FamilyKitchenCleanliness

Guest suite in North Fork

The exterior of a historic Tudor home is shown, featuring a blend of brick and wood accents. A winding driveway leads to the entrance, surrounded by lush greenery and a decorative black fence. Trees provide shade, enhancing the serene outdoor setting.

4.88 out of 5 average rating, 737 reviews

Walk to Vineyards, Beaches, Farms & Town

Private bungalow with a separate entrance in a historical tudor home. Spacious bedroom with king-sized bed, kitchenette and bathroom. Two bikes, cable TV, internet, AC, beach towels, parking, snacks, coffee and water all provided. Walking distance to the beach, restaurants, shops, vineyards, grocery, farms and fish market. Jitney stop is one block away!

FamilyIndoor spacesGetting around

Apartment in Shelter Island Heights

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.

4.9 out of 5 average rating, 270 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

Indoor spacesKitchenComfort

Popular amenities for Shelter Island family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.96 out of 5 average rating, 107 reviews

A vibrant pool scene is captured, featuring a colorful unicorn float positioned on the water. Lush hydrangea blooms frame the area in shades of pink, complementing the surrounding greenery and the wooden fence that provides privacy.

Apartment in Southampton

Swimming pool w/Hot tub Fire Pit Coffee Bar

Indoor spacesFamilyQuiet

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

KitchenFamilyQuiet

4.83 out of 5 average rating, 219 reviews

The living area is characterized by high vaulted ceilings and large windows allowing natural light. A sofa with light cushions is centered around a wooden coffee table on a neutral rug. A decorative fireplace is framed with a modern mantle, adding warmth to the space.

Home in Southampton

Stylish & Chic w hot tub/ Near Beaches & Village

Indoor spacesFamilyWi-Fi

4.99 out of 5 average rating, 211 reviews

A screened-in patio features a wooden ceiling and overhead fans, providing a comfortable space for relaxation. A navy blue sofa pairs with a coffee table, while tall chairs surround a dining table. Views of a spacious yard and trees are visible through the screens.

Home in Greenport

Greenport Village walking distance to all

KitchenFamilyPool

4.92 out of 5 average rating, 512 reviews

A spacious living area features a dark leather sofa adorned with colorful throw pillows, complimented by a patterned area rug. A ceiling fan is positioned above, and natural light streams through multiple windows. An adjoining dining area with a black table and chairs is visible.

Home in Greenport

Blue Bay Dream (Outdoor Jacuzzi, Cabana + Office)

Indoor spacesKitchenAmenities

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

FamilyIndoor spacesBeach

Home in Westhampton Beach

4.94 out of 5 average rating, 117 reviews

Brand new house with an all year round hot tub.

Indoor spacesFamilyBathroom

4.83 out of 5 average rating, 138 reviews

An outdoor area features a rectangular pool surrounded by a wooden deck. Lounge chairs are positioned along the pool's edge, and a shaded seating area is located nearby under an umbrella. Lush trees provide privacy and a natural backdrop.

Home in Springs

East Hampton Oasis - Pool and Hot Tub

KitchenIndoor spacesBackyard

Family- and pet-friendly home rentals

4.98 out of 5 average rating, 181 reviews

A light-filled living space is highlighted by a wall of glass, providing expansive views of the water and a natural landscape. The space includes a round coffee table on a light floor, with comfortable seating arranged to enjoy the serene outdoor scenery.

Cottage in Riverhead

Savor Ocean Sunsets at a Soothing Beachfront Haven

FamilyIndoor spacesAccuracy

4.97 out of 5 average rating, 158 reviews

A spacious backyard is enclosed by a white picket fence, featuring a large umbrella-shaded dining table with chairs. Lush greenery surrounds the area, complemented by a sunny sky and quaint shed in the background. The scene invites relaxation and outdoor enjoyment.

Home in Greenport

Cosy North Fork Cottage with large backyard

FamilyIndoor spacesNearby

4.95 out of 5 average rating, 201 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

FamilyKitchenCheckout

4.99 out of 5 average rating, 130 reviews

The living area features two rattan chairs facing a coffee table, surrounded by vibrant wall art. A cozy sofa and plants add life to the space. Natural light streams through large windows, creating a bright and inviting atmosphere.

Home in Montauk

3 BR/Pool. Walk to Beach & Town!

KitchenIndoor spacesParking

4.85 out of 5 average rating, 155 reviews

Home in Hampton Bays

Hamptons Oceanfront Oasis

KitchenIndoor spacesCheckout

4.9 out of 5 average rating, 116 reviews

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.

Home in Sag Harbor

The Cooper-Burke House

FamilyKitchenWi-Fi

5.0 out of 5 average rating, 111 reviews

A spacious backyard is framed by mature trees, featuring a fire pit surrounded by white Adirondack chairs. A children’s playground with swing set is visible nearby, while the home, illuminated by warm lights, stands invitingly in the background.

Villa in Southampton

Hamptons WaterLiving-Dock, Kayak, Beach, EV charge

FamilyKitchenLayout

4.94 out of 5 average rating, 102 reviews

The backyard showcases a serene oasis with a sparkling pool surrounded by lush greenery. A sunroom is visible, providing a view of the inviting outdoor space. The setting offers a sense of privacy, enhanced by the natural landscape.

Home in Springs

Oasis backyard, Pool, Gym, and Sunroom!

KitchenIndoor spacesTV

Family-friendly home rentals with a pool

4.9 out of 5 average rating, 124 reviews

Apartment in Southampton

Oasis Hampton getaway

Indoor spacesKitchenLayout

Home in Westhampton Beach

A charming cottage exterior features wood shingles and white trim. An American flag hangs proudly from the front, while window boxes with greenery add a touch of color. The light blue front door complements the natural elements, inviting guests inside.

4.98 out of 5 average rating, 170 reviews

Luxury Hamptons Home with Heated Saltwater Pool

KitchenFamilySleep quality

4.99 out of 5 average rating, 123 reviews

A well-maintained outdoor space features a large swimming pool surrounded by a wooden deck. Lounge chairs are placed around the pool, with red umbrellas providing shade. Adjacently, a patio area includes a dining table. Lush greenery frames the area, contributing to a serene ambiance.

Guesthouse in Springs

The Quail’s Nest

KitchenFamilyHospitality

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, 76 reviews

Bayfront 1BR/2BR detached guesthouse with pool

KitchenIndoor spacesLocation

5.0 out of 5 average rating, 9 reviews

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

KitchenIndoor spacesPool

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

KitchenFamilyAir 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

Indoor spacesKitchenHot tub

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.