
Pet-friendly holiday rentals in Shelter Island
Find and book unique pet-friendly homes on Airbnb
Top-rated pet-friendly home rentals in Shelter Island
Guests agree: These pet-friendly homes are highly rated for location, cleanliness and more.

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.

Serene | Pool | 1 block to waterfront dining
Escape to your chic, serene Hamptons oasis! Enjoy the privacy of your own home just steps to waterfront dining + more Relax poolside, spark up the BBQ + firepit under the starry sky, swim + enjoy the peace + tranquility of this property. Enjoy easy living + convenience; walk 1 block to waterfront dining + cafe. Sip cocktails while you watch the most magnificent sunsets + have morning coffee on the sea. Stream on your 80' TV You'll be 8 minutes to Main St, shopping, beaches, restaurants + more!

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!

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.

Shelter Island getaway steps from beaches
Just 2 blocks from Hay Beach, our family & pet-friendly 3BR home offers space to relax & play. Enjoy a large yard w/ fire pits, beach gear, games, & toddler toys. Inside: open living area, fireplace, full kitchen, 2 baths, playroom, workout space, & extra sleeping options. Quiet neighborhood, perfect for families. Winter stays: cozy up by the fire & enjoy $0 cleaning fee Nov–Mar. Host lives next door for quick support. For the littles there is a full sized crib high chair and bathtub.

Private & Cozy Cottage with short walk to beach!
Walking distance to Bay Beach & Rumba, & short drive to town & ocean. Quiet neighborhood, great for couples, King bed upstairs, bit of a steep staircase, so may not be suited for anyone with mobility challenges. Kayaks, paddle-boards, available to enjoy. Dog friendly with fenced in patio and doggy door. Private outdoor patio, with charcoal grill. A/C & Heat for year-round enjoyment. Easy to get in/out from the city. Close drive to visit Westhampton and Southampton Main Streets.

Private & Pristine with Pool and Kid’s Playard
INSTANT BOOK/ dates are current. Private and Pristine 3 bed / 2 bath home in the heart of East Hampton set on 1.3 acres. Home features a chef's kitchen, in-ground gated pool, and pure privacy and relaxation. Close proximity to East Hampton Village (5 mins) and East Hampton, Amangansett and Bay Beaches (7mins), Montauk (20 mins), Sag Harbor (15 mins). Kids adore the huge playground! Entire property fenced-in to ensure the safety of kids! Heated Pool open: Memorial Day - Sept 30.

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.

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

Corwin House

Stunning Southampton Star

Stylish Beach Getaway: pool & walking location

Walk to Beach, Stunning Sunsets!

Enchanted Story Book Home

Charming Retreat Near Ocean Beaches

1800 Historical EH Home, 1 Mile to Town!

5BR/3BA: Shelter Island, Waterview, Close to beach
Pet-friendly home rentals with a pool

Modern East Hampton Home w/ Heated Saltwater Pool

Clean Home Pool Cent-Loc. Quiet Reserve Pet Friend

North Fork Sound Front Home with Pool

East Hampton Secluded Escape with Gunite Pool

Long Island home with pool 1 mile from Greenport

Head of Pond House - Waterfront Cottage

Gorgeous Waterfront and Indoor Pool Family Oasis!

Coastal Retreat|Heated Saltwater Pool|5 MinToBeach
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

Southold- Adorable 1 Bedroom Cottage

Scandinavian Cottage

Beach Cottage 2 | New Suffolk | North Fork
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!
Destinations to explore
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- Rentals with pools Shelter Island
- Rentals with a fireplace Shelter Island
- Family-friendly rentals Shelter Island
- Rentals with a hot tub Shelter Island
- Rentals with a patio Shelter Island
- Waterfront rentals Shelter Island
- Rentals with a washing machine and dryer Shelter Island
- Rentals with beach access Shelter Island
- Rentals with a fire pit Shelter Island
- House rentals Shelter Island
- Beachfront rentals Shelter Island
- Rentals with a kayak Shelter Island
- Rentals with outdoor seating 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





