
Pet-friendly holiday rentals in Shelter Island
Find and book unique pet-friendly homes on Airbnb
Quick stats about holiday rentals that are pet-friendly in Shelter Island

Total holiday rentals
Explore 50 holiday rentals in Shelter Island

Nightly prices starting at
Shelter Island holiday rentals start at $250 AUD per night before taxes and fees

Verified guest reviews
Over 1,310 verified reviews to help you choose

Family-friendly holiday rentals
50 properties offer extra space and kid-friendly amenities

Holiday 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 holiday 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.

Pool + Zen I 1 block to water, 8 mins. to Main St.
Escape to your serene, chic Hamptons oasis! Located just 1 block to the best waterfront dining + 8 mins. to Main St. shopping! Enjoy your gorgeous outdoor and indoor space - swim all day in your pool, spark up the BBQ + fireplace under the starry sky. Cook up a meal in your Chef's kitchen and eat outside on the porch. Curl up to your 80' streaming TV. Stroll just 1 block to the best waterfront restaurants for dinner, cocktails + coffee on the water. Drive 8 minutes to Main Street for shopping!

Private beach, fully updated house, on 2 acres.
Each the special magic that only the Hamptons offer—historic charm, a rural atmosphere, white sandy beaches and a relaxed lifestyle—while staying in this light-filled three-story cottage. Tucked away on a beautiful 2.2-acre wooded lot, this bayside oasis offers a tranquil retreat, with deer sightings, private beach access, stunning view and picture-perfect sunsets. A short drive to the beaches and town, quick trips to nearby shops, market stands, restaurants, museums and Jackson Pollack house.

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.

Walk to Village Sag Harbor Victorian
Charming 2 bedroom 2 bathroom house in the historic Village of Sag Harbor with view of pond and park. Walking distance (not driving) to the quaint village with restaurants, shops, long wharf, gym, yoga. Living room with fireplace, dining room, kitchen and office. Upstairs loft ensuite bedroom and bathroom. Downstairs bedroom and full bath with tub and shower. Flower filled back deck with BBQ. Wireless internet, 2 TV's, air conditioner units, washer dryer. Minutes to ocean and bay beaches.

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.

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!

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.

Summer Retreat at the beach , enjoy Wine Country
* We provide a Beach Parking Pass for all Southold Town Beaches * 10 min walk to neighborhood sandy beach! * 5 min walk to vineyard with tasting room. Spacious Contemporary home. Master Bedroom plus 2 more bedrooms and 2 bathrooms on the second floor. Living room & kitchen on main floor. Wake up to beautiful garden view. Large kitchen and dining area for the whole family. Just minutes from Long Island's wineries and wedding venues. This home comes complete with everything you need!

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.

Breezy Waterfront Home With private Dock
This charming waterfront home is the ideal getaway for the active family with the Hamptons' largest natural 'saline pool' (the Peconic Bay) just footsteps away. This home easily sleeps 7 - with 3 bedrooms and 3 separate kids' sleeping cabins. You can jump on our standup paddle board right off our private dock, jog along wide stretches of pebble beach, have a swim race to our floating swim platform or simply relax in the hammock. 2 bathrooms indoors and 1 private outdoor shower,

Charming Southampton Light filled Cottage
Escape and relax in this beautiful tranquil Southampton retreat! Newly remodeled cottage just blocks from the water. The home is nestled on 1/2acre quiet park-like setting located at the end of a long gravel driveway. Enjoy the private outdoor space with a fire pit, outdoor dining table, new dual BBQ and lounge chairs. Inside, the large dining room table easily sits 8. This stylish Coastal farmhouse has all new beds and furniture. Complete with Wifi, Cable, AC and Nespresso maker!

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.
Popular amenities for Shelter Island pet-friendly home rentals
Pet-friendly house rentals

Corwin House

Waterfront NoFo Cottage w/ public beach access

Stunning Southampton Star

Walk to Beach, Stunning Sunsets!

Beautiful Southampton Home w/Pool, Walk to US Open

5BR/3BA: Shelter Island, Waterview, Close to beach

Walk to town, Greenport Village - Harbor Views

North Fork Paradise
Pet-friendly home rentals with a pool

Modern East Hampton Home w/ Heated Saltwater Pool

Stylish Beach Getaway: pool & walking location

Clean Home Pool Cent-Loc. Quiet Reserve Pet Friend

North Fork Sound Front Home with Pool

East Hampton Secluded Escape with Gunite Pool

Montauk Oceanview with Fireplace (2)

Head of Pond House - Waterfront Cottage

Gorgeous Waterfront and Indoor Pool Family Oasis!
Private, pet-friendly home rentals

Hamptons Tiny House!

SPA DEPARTURES NEAR THE SEA

Newly renovated farmhouse - steps to Village

Victorian Pearl

Peconic Sound Beach Cottage | Walk to Sound

Enchanted Story Book Home

Enchanting studio cottage, walk everywhere

Scandinavian Cottage
When is the best time to visit Shelter Island?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $904 AUD | $546 AUD | $758 AUD | $860 AUD | $990 AUD | $1,111 AUD | $1,424 AUD | $1,318 AUD | $875 AUD | $708 AUD | $739 AUD | $694 AUD |
| 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 |
Destinations to explore
- Plainview Holiday rentals
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- Rentals with a patio Shelter Island
- Rentals with a kayak Shelter Island
- Rentals with beach access Shelter Island
- Waterfront rentals Shelter Island
- House rentals Shelter Island
- Rentals with pools Shelter Island
- Rentals with a hot tub Shelter Island
- Rentals with a washing machine and dryer Shelter Island
- Rentals with outdoor seating Shelter Island
- Rentals with a fireplace Shelter Island
- Family-friendly rentals Shelter Island
- Rentals with a fire pit Shelter Island
- Beachfront rentals Shelter Island
- Pet-friendly rentals Suffolk County
- Pet-friendly rentals New York
- Pet-friendly rentals United States
- Yale University
- Cooper's Beach, Southampton
- Fairfield Beach
- Charlestown Beach
- Southampton Beach
- Ocean Beach Park
- East Matunuck State Beach
- Mohegan Sun
- Sunken Meadow State Park
- Hammonasset Beach State Park
- Point Judith Lighthouse
- Mystic Seaport Museum
- Powder Ridge Mountain Park & Resort
- Yale University Art Gallery
- Sleeping Giant State Park
- Long Island Aquarium
- Mount Southington Ski Area
- Amagansett Beach
- Burlingame State Park
- Ocean Beach
- Orient Beach State Park
- Mystic Aquarium
- Wölffer Estate Vineyard
- Foxwoods Resort Casino





