
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$37,674 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.

Serene w/ large pool ~1 block to waterfront dining
Serene, chic, Hamptons oasis! 1 block to waterfront dining + 8 minutes to Main St. + beaches Enjoy your calm, zen, private home nestled in nature + peacefulness. Swim in your pool all day, spark up the firepit + BBQ under the starry sky! Curl up in the living room; cook in the Chef's kitchen + stream on the 80' TV. Enjoy a 1 block stroll to waterfront dining + cafe for coffee on the sea + dinner/drinks watching the sunset over the harbor You'll be 8 mins to Main St., beaches + so much more!
Outdoor spacesWalkabilityAccuracy

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.
WalkabilityOutdoor spacesHospitality

Hamptons Oceanfront Oasis
Escape the hustle & bustle of city life and unwind at this stunning home in the Hamptons. The oceanfront oasis is the perfect way to wake up to ocean views, beaches and nearby restaurants. Relax on our spacious deck - perfect for morning coffees & sunset cocktails. It is just a short drive to the train station & only 15 minutes from the airport for quick getaways. For your safety, the home is equipped with Ring cameras and one-use key codes. Book now and experience the ultimate Hamptons escape!
WalkabilityPetsGetting around

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.
Outdoor spacesPetsView

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.
Outdoor spacesPetsHospitality

PICTURE PERFECT SOUTHAMPTON HOME-
Picture Perfect 3 bedroom 1.5 Bath Cottage located in the heart of Southampton. The home is conveniently located close to Southampton, Bridgehampton and Sag Harbor towns. Additionally, there is close access to both Bay and Ocean Beaches. The Newly renovated home gives you a peaceful and serene feeling everyday. Dogs are accepted on a case by case basis. Cats are not permitted. Please read the additional disclosures, guidelines, and rules. No events, no parties, no smoking –
WalkabilityPetsCheckout

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.
WalkabilityPetsCheckout

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.
PetsWalkabilityAccuracy

Southamp Waterview, DogsFREE! Kayaks, Ping-Pong
Beachy casual feel-good home easily located at the entrance to The Hamptons. Lovely views of Bay, Nightly Sunsets & birds! Launch our Kayaks at street's tiny beach flowing from Cold Spring Pond into Bay. Or cuddle by the fireplace and play our many available games. We provide soft sheets & towels for the showers and & beach...priding ourselves on your comfort! Our Private-Pool is heatable & plant-surrounded with Outdoor Shower.
PetsWalkabilityBathroom

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.
WalkabilityOutdoor spacesGetting around

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.
PetsWalkabilityBathroom

Walk to Breakwater Beach in Heart of Wine Country
Private and peaceful cottage walking distance to Breakwater Beach and Old Mill Inn Restaurant on the water opening Spring 2025. There are two large decks to relax by the firepit and drink your wine from the local wineries. Bikes, kayak, and paddle board are stored in the barn for guests use. Easy access to the marina, fishing, fine dining, vineyards, and farm stands.
Outdoor spacesWalkabilityCheck-in
Popular amenities for Shelter Island pet-friendly home rentals
Pet-friendly house rentals

Silver House: 3BR Home with Private Beach Access
Outdoor spacesWalkabilityBackyard

Explore the Water & Woods at a Relaxing Retreat
PetsWalkabilityCheck-in

Montauk Private Beach Bungalow
WalkabilityPetsQuiet

Family Retreat with Heated Pool, Hot Tub, Sauna.
WalkabilityOutdoor spacesKitchen

Greenport Village walking distance to all
WalkabilityPetsGrill

Sea Roost
Outdoor spacesPetsCondition

Laid Back Relaxation
WalkabilityOutdoor spacesFamily

Beautiful beach home with pool & water views!
Outdoor spacesWalkabilityAmenities
Pet-friendly home rentals with a pool

Swimming pool w/Hot tub Fire Pit Coffee Bar
PetsWalkabilityValue

PRIVATE BASEMENT APARTMENT WITH POOL IN SAG HARBOR
WalkabilityPetsSleep quality

East Hampton Oasis - Pool and Hot Tub
WalkabilityOutdoor spacesComfort

Modern East Hampton Home w/ Heated Saltwater Pool
Outdoor spacesWalkabilityAir conditioning

Private & Pristine with Pool and Kid’s Playard
Outdoor spacesWalkabilityComfort

1800 Historical EH Home, 1 Mile to Town!
PetsWalkabilityKitchen

Astounding Watermill 5 Bedroom home with Pool
PetsOutdoor spacesAccuracy

Stunning Hamptons Waterfront Escape w/ Sunset View
WalkabilityPetsCondition
Private, pet-friendly home rentals

Hamptons WaterLiving-Dock, Kayak, Beach, EV charge
Outdoor spacesWalkabilityLong stay

Cozy Shelter Island 2 Bedroom 1 Bath Cottage
WalkabilityOutdoor spacesNearby

Kenney's Beach Loft - Vineyards, Horton Lighthouse
Outdoor spacesWalkabilityBathroom

New Bridgehampton Sag Harbor Hamptons Cottage
PetsHot tubComfort

Luxe|Pool|BeachCar|Games|Movie|HotTub|Firepit
Outdoor spacesDecorCheckout

Walk to Beach and Greenport Village, Two King Beds
PetsOutdoor spacesTV

Hidden Garden Cottage|Beach|Pet Friendly
Outdoor spacesWalkabilityIndoor spaces

The North Star: Greenport Waterview Beach Getaway
WalkabilityPetsNearby
When is the best time to visit Shelter Island?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$136,253 GYD | G$82,254 GYD | G$114,276 GYD | G$130,811 GYD | G$124,323 GYD | G$156,973 GYD | G$214,530 GYD | G$198,623 GYD | G$131,857 GYD | G$106,742 GYD | G$111,346 GYD | G$104,649 GYD |
| Avg. temp | 0°C | 1°C | 4°C | 10°C | 16°C | 21°C | 24°C | 24°C | 20°C | 14°C | 8°C | 3°C |
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- Rentals with pools Shelter Island
- Rentals with a hot tub Shelter Island
- Family-friendly rentals Shelter Island
- Rentals with beach access Shelter Island
- Rentals with a kayak Shelter Island
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- Pet-friendly rentals Suffolk County
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- Yale University
- Mohegan Sun
- Foxwoods Resort Casino
- Cooper's Beach, Southampton
- East Matunuck State Beach
- Fairfield Beach
- Ocean Beach Park
- Charlestown Beach
- Mystic Aquarium
- Mystic Seaport Museum
- Point Judith Lighthouse
- Southampton Beach
- Sunken Meadow State Park
- Soundview Beach
- Hammonasset Beach State Park
- Powder Ridge Mountain Park & Resort
- Ocean Beach
- Sleeping Giant State Park
- Wölffer Estate Vineyard
- Yale University Art Gallery
- Orient Beach State Park
- Meschutt Beach
- Wesleyan University
- Long Island Aquarium





