
Pet-friendly holiday rentals in Shelter Island Heights
Find and book unique pet-friendly homes on Airbnb
Top-rated pet-friendly home rentals in Shelter Island Heights
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.

Whaling Captain Pierson's Cottage
Whaling Captain Pierson's Cottage is at a waterfront property. A unique environmental experience, nestled in nature but only a 7 minutes’ walk from the center of historic Sag Harbor Village. It is the only cottage offering a vast, picturesque, panoramic view of beautiful Sag Harbor Cove from Main Street as well as spectacular sunsets and a private low-tide beach. (See my reviews from my other listings entitled, "Whaling Captain Pierson's Apartment" and "Whaling Captain Pierson's Apartment TOO".)

Montauk Private Beach Bungalow
Beautiful secluded cottage tucked away at the end of cul-de-sac and surrounded by a nature preserve. Montauk’s finest waterfront dining and bars are less than a mile. The house has a large living room with a fireplace, king bed in one and a full bed with a twin bunk in the other, a full bath, and an eat-in kitchen with dining for 6. There is a large very private patio with a grill, dining table and lounge area. The private beach is stunning and a 3 minute walk from the house. Pets are welcome.

Serenity + privacy; 1 block to waterfront dining
Serene, chic, vibes await you at your Hamptons oasis! Enjoy the privacy of your own home located just minutes to the water + Main St. Hang poolside or on the porch + enjoy the bucolic views. Spark up the firepit + BBQ under the starry sky! Soak up the nature and calm vibes here. Stream on your 80' TV. Walk 1 block to waterfront cafe + dining for coffee on the sea + dinner/cocktails while watching the sunset over the harbor. You'll be 8 mins to Main St. shopping, beaches, bays + so much more.

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!

Calf Creek Cottage (Water Mill/Bridgehampton)
Enjoy the peaceful seclusion of this charming, updated 3 bedroom, 2 bath cottage located on a private, acre-sized flag-lot south of the highway right on the border of Water Mill and Bridgehampton. Each bedroom (1 king, 2 queen) features ample closet space and new smart TVs . The new, fully-stocked kitchen, propane BBQ, outdoor dining table for 8, outdoor shower and spa with lounge furniture, and wood burning fireplace make it the perfect getaway for either summer or the winter season. Pets OK.

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

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 .

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.

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.

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.

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

Private & Pristine with Pool and Kid’s Playard

Summer Retreat at the beach , enjoy Wine Country

Modern Farmhouse Retreat North Fork Wine Country

Sunlit cozy cottage by the bay.

Amazing Home close to Everything -

Sweeping Dunes Beach Cottage

Luxe Southampton Home w/Pool 5 Min Walk to US Open

Designer home in Sag Harbor : 5BR walk to beach
Pet-friendly home rentals with a pool

POOL + Beach Oasis! Winter deals 2+ nights!

4 BD w/ Heated Pool in E Hampton, Fully Furnished

Beautiful condo on Long Islands Northfork

Stylish Beach Getaway: pool & walking location

Bright Hamptons Getaway ☀️ Pool▪︎ Beach▪︎FamilyFun

1800 Historical EH Home, 1 Mile to Town!

Head of Pond House - Waterfront Cottage

Montauk Oceanview
Private, pet-friendly home rentals

Victorian Pearl

Classic Hamptons Cottage - Heart of Amagansett

Greenport Saltbox | North Fork Wine Retreat

The Big Easy... A gentle, slow and easy going stay

Enchanted Story Book Home

Bay View Cottage - Steps to Bay Private Beach

Sparkling East Hampton Oasis 3/2, heated pool

Southold- Adorable 1 Bedroom Cottage
When is the best time to visit Shelter Island Heights?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £355 | £314 | £299 | £344 | £404 | £451 | £501 | £510 | £424 | £374 | £374 | £369 |
| 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 |
Quick stats about holiday rentals that are pet-friendly in Shelter Island Heights

Total holiday rentals
Explore 140 holiday rentals in Shelter Island Heights

Nightly prices starting at
Shelter Island Heights holiday rentals start at £97 per night before taxes and fees

Verified guest reviews
Over 5,900 verified reviews to help you choose

Family-friendly holiday rentals
120 properties offer extra space & child-friendly amenities

Holiday rentals with a pool
50 properties feature pools

Rentals with dedicated workspaces
90 properties have a dedicated workspace

Wifi availability
140 of Shelter Island Heights holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Shelter Island Heights rentals

4.9 Average rating
Shelter Island Heights stays are highly rated by guests – averaging 4.9 out of 5!
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- Rentals with a patio Shelter Island Heights
- Rentals with outdoor seating Shelter Island Heights
- Fitness-friendly rentals Shelter Island Heights
- Rentals with a kayak Shelter Island Heights
- House rentals Shelter Island Heights
- Rentals with a firepit Shelter Island Heights
- Rentals with pools Shelter Island Heights
- Waterfront rentals Shelter Island Heights
- Rentals with a fireplace Shelter Island Heights
- Rentals with a hot tub Shelter Island Heights
- Beachfront rentals Shelter Island Heights
- Rentals with a washing machine and dryer Shelter Island Heights
- Flat rentals Shelter Island Heights
- Rentals with beach access Shelter Island Heights
- Rentals with breakfast Shelter Island Heights
- Apartment rentals Shelter Island Heights
- Family-friendly rentals Shelter Island Heights
- Boutique hotels Shelter Island Heights
- Pet-friendly rentals Suffolk County
- Pet-friendly rentals New York
- Pet-friendly rentals United States
- Beach
- Yale University
- Cooper's Beach, Southampton
- Fairfield Beach
- East Matunuck State Beach
- Charlestown Beach
- Mohegan Sun
- Ocean Beach Park
- Southampton Beach
- Foxwoods Resort Casino
- Mystic Seaport Museum
- Sunken Meadow State Park
- Point Judith Lighthouse
- Hammonasset Beach State Park
- Powder Ridge Mountain Park & Resort
- Sleeping Giant State Park
- Long Island Aquarium
- Yale University Art Gallery
- Wölffer Estate Vineyard
- Mount Southington Ski Area
- Blue Shutters Beach
- Orient Beach State Park
- Meschutt Beach
- Ocean Beach





