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Pet-friendly vacation rentals in Shelter Island

Find and book unique pet-friendly homes on Airbnb

Quick stats about vacation rentals that are pet-friendly in Shelter Island

  • Total vacation rentals

    Explore 50 vacation rentals in Shelter Island

  • Nightly prices starting at

    Shelter Island vacation rentals start at G$37,651 GYD per night before taxes and fees

  • Verified guest reviews

    Over 1,410 verified reviews to help you choose

  • Family-friendly vacation rentals

    40 properties offer extra space & kid-friendly amenities

  • Vacation rentals with a pool

    30 properties feature pools

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    50 of Shelter Island vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Shelter Island rentals

  • 4.9 Average rating

    Shelter Island stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated pet-friendly home rentals in Shelter Island

Guests agree: these pet-friendly homes are highly rated for location, cleanliness, and more.

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Top guest favorite
Home in Shelter Island Heights

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, sleek 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

4.92 out of 5 average rating, 100 reviews
Top guest favorite
The exterior of the farmhouse is framed by well-maintained hedges, with a simple wooden staircase leading to the front door. Brightly lit windows are positioned symmetrically, highlighting the home's classic architecture. The surrounding greenery complements the inviting entrance.
Home in Greenport

Cozy Farmhouse Retreat in North Fork, NY

A 1905 farmhouse with modern touches, Arthur's Vineyard is a cozy 3-bed, 2-bath home in walking distance of Greenport village's beaches, marina, restaurants and boutiques. An open plan living area, breezy decor and a large landscaped backyard for spending relaxed summer days and nights with your family and friends, including the 4-legged ones. Walk to the train station/jitney or take a short drive to the wineries & farm stands of the North Fork. Recent updates: central heat/AC & new bathrooms.

4.92 out of 5 average rating, 136 reviews
Guest favorite
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.

4.93 out of 5 average rating, 138 reviews
Top guest favorite
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

Newly renovated and featured as a top Airbnb by New York Magazine, The Beach Cottage has been designed and decorated in a modern organic style, with a palette of whites and neutrals to create a serene and peaceful escape. Relax in the airy, light and open living room, which features a wall of glass for indoor/outdoor living with expansive, uninterrupted water views. Stay on the property for swimming, beach walks, sunsets and BBQs - or venture out to enjoy all the North Fork has to offer.

4.98 out of 5 average rating, 184 reviews
Guest favorite
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

4.96 out of 5 average rating, 189 reviews
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.
Home in Sag Harbor

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

4.86 out of 5 average rating, 139 reviews
Top guest favorite
A comfortable living room area is presented, featuring a light-colored sectional sofa arranged around a wooden coffee table. Natural light enters through a large window, illuminating a piece of artwork on the wall and adding a cozy touch to the space.
Apartment in Sag Harbor

PRIVATE BASEMENT APARTMENT WITH POOL IN SAG HARBOR

Beautiful basement apartment partially in-ground, with many windows and private entrance is located in Sag Harbor , 3 minutes from village and Heavens Bech by car or 15 minutes walking distance . The apartment has king size bed and comfortable sofa in the living room . In the kitchen you can find coffe maker , toaster , microwave, dishwasher, small fridge , hot plate for light cooking . Tv , WiFi , Airconditoining , access to pool from May till end of the September .

4.93 out of 5 average rating, 158 reviews
Guest favorite
Home in Shelter Island Heights

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.

4.9 out of 5 average rating, 130 reviews
Top guest favorite
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

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.

4.9 out of 5 average rating, 119 reviews
Guest favorite
A cozy living area features a brown sectional sofa adorned with patterned throw pillows. A black coffee table sits on a striped area rug, providing a neutral contrast to the light hardwood flooring. Natural light filters through multiple windows, enhancing the welcoming ambiance.
Apartment in Greenport

Harbor Heights

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 2nd 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.

4.94 out of 5 average rating, 248 reviews
Guest favorite
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

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.

4.93 out of 5 average rating, 109 reviews
Top guest favorite
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.
Guest suite in North Fork

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!

4.88 out of 5 average rating, 755 reviews

Popular amenities for Shelter Island pet-friendly home rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Pet-friendly house rentals

Guest favorite
A serene scene features a well-kept pool surrounded by lounge chairs, reflecting the colors of the sunset. The main house and pool house are visible, each with large windows and inviting outdoor spaces. Lush greenery outlines the property, enhancing the tranquil setting.
Home in Hampton Bays

Stunning Hamptons Waterfront Escape w/ Sunset View

4.87 out of 5 average rating, 144 reviews
Guest favorite
A bright living area features a light grey sofa paired with two black chairs, positioned around a glass coffee table. Large windows allow natural light to fill the space, while a minimalist fireplace offers visual interest. A small desk is visible against the wall.
Home in Springs

Silver House: 3BR Home with Private Beach Access

4.95 out of 5 average rating, 524 reviews
Superhost
The airy living space features white shiplap walls and a high ceiling, accented by natural light from multiple windows. A gray sofa is paired with a glass coffee table, while a decorative fireplace adds charm. A ceiling fan provides airflow, enhancing the inviting atmosphere.
Home in Southampton

PICTURE PERFECT SOUTHAMPTON HOME-

4.89 out of 5 average rating, 312 reviews
Guest favorite
A spacious backyard is bordered by lush greenery and has a view of the tranquil water. Two surfboards are propped against the house, and a set of bright pink chairs surrounds a dining table. Pathways made of stones lead to the water's edge.
Home in Shelter Island

Waterfront shelter island gem

4.96 out of 5 average rating, 45 reviews
Top guest favorite
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.
Home in Shelter Island Heights

Laid Back Relaxation

5.0 out of 5 average rating, 23 reviews
Guest favorite
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.
Home in Shelter Island Heights

Silver Beach, 3 Bedroom cottage w/ pool

4.91 out of 5 average rating, 56 reviews
Superhost
Home in Sag Harbor

Heated Pool and Spa in Sag Harbor w/ Tennis Access

4.88 out of 5 average rating, 16 reviews
Guest favorite
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

4.87 out of 5 average rating, 46 reviews

Pet-friendly home rentals with a pool

Guest favorite
A well-designed outdoor area features a pristine pool with colorful floats, bordered by a spacious deck. Lounge chairs, adorned in striped blue and white, provide comfortable seating under large umbrellas. The house is illuminated, showcasing a welcoming atmosphere amidst lush greenery.
Villa in East Hampton

Pool|Golf Sim|HotTub|Movie|Games|Firepit|Golf Open

4.95 out of 5 average rating, 101 reviews
Top guest favorite
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

4.96 out of 5 average rating, 222 reviews
Guest favorite
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

4.94 out of 5 average rating, 167 reviews
Luxe
Home in Springs

East Hampton Home: Heated Pool, Gym, Fully Fenced

4.97 out of 5 average rating, 112 reviews
Superhost
An airy living space features exposed wooden beams and large windows allowing natural light to fill the room. A modern yellow sofa and a dining table with elegant chairs create a welcoming atmosphere. Decorative elements include a gold-framed artwork and bronze accent tables on a soft area rug.
Home in Water Mill

Designer's Own, w Pool, 5 min. to Ocean & Village

4.88 out of 5 average rating, 105 reviews
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, 119 reviews
Guest favorite
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 wIth Fire Pit /Coffee Bar

4.96 out of 5 average rating, 110 reviews
Top guest favorite
A heated saltwater pool is surrounded by a spacious green lawn and lounge chairs, with a tree-lined white fence in the background. The house features a charming design with large windows and a wide patio area, suitable for outdoor dining and relaxation.
Home in Hampton Bays

Stylish+Modern Cape w/Saltwater Pool-5min to Beach

4.97 out of 5 average rating, 159 reviews

Private, pet-friendly home rentals

Guest favorite
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

5.0 out of 5 average rating, 117 reviews
Guest favorite
An open-concept living space features a modern dining area with a wooden table set for six, complemented by sleek metallic chairs. A comfortable sectional sofa is positioned across from a wall-mounted television, with a fireplace and green outdoor views visible through large windows.
Cottage in Bridgehampton

Calf Creek Cottage (Water Mill/Bridgehampton)

4.95 out of 5 average rating, 110 reviews
Guest favorite
Cottage in Shelter Island

Cozy Shelter Island 2 Bedroom 1 Bath Cottage

4.95 out of 5 average rating, 57 reviews
Top guest favorite
The exterior of the cottage is highlighted by a well-maintained yard featuring a lush green lawn. A patio area with seating is visible, surrounded by flowering shrubs and trees. Multiple large windows offer a view into the inviting living spaces within.
Home in North Fork

Waterfront Beach Cottage

4.95 out of 5 average rating, 77 reviews
Superhost
Home in East Hampton

Contemporary house East Hampton with heated pool

5.0 out of 5 average rating, 8 reviews
Guest favorite
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

4.88 out of 5 average rating, 24 reviews
Top guest favorite
A spacious lawn is bordered by tall trees, providing a natural frame for the cottage. The vibrant green grass leads to a serene waterfront, where the lake reflects the sunlight. The peaceful setting invites relaxation and outdoor activities.
Cottage in Water Mill

Head of Pond House - Waterfront Cottage

4.98 out of 5 average rating, 80 reviews
Top guest favorite
An open-concept living space features a round dining table surrounded by four chairs, complemented by a decorative pouf. A modern kitchen with stainless steel appliances is visible, along with large windows that provide abundant natural light and views of the outdoor greenery.
Home in North Fork

Private North Fork Cottage- Walk to Beach!

4.9 out of 5 average rating, 48 reviews

When is the best time to visit Shelter Island?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$136,172 GYDG$82,205 GYDG$114,209 GYDG$130,733 GYDG$124,249 GYDG$156,880 GYDG$214,403 GYDG$198,505 GYDG$131,779 GYDG$106,678 GYDG$111,280 GYDG$104,587 GYD
Avg. temp0°C1°C4°C10°C16°C21°C24°C24°C20°C14°C8°C3°C

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