
House holiday rentals in Shelter Island
Find and book unique houses on Airbnb
Quick stats about house rentals in Shelter Island

Total holiday rentals
Explore 110 holiday rentals in Shelter Island

Nightly prices starting at
Shelter Island holiday rentals start at $17 NZD per night before taxes and fees

Verified guest reviews
Over 2,290 verified reviews to help you choose

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

Pet-friendly accommodation
Find 40 rentals that welcome pets

Holiday rentals with a pool
50 properties feature pools

Rentals with dedicated workspaces
60 properties have a dedicated workspace

Wi-Fi availability
110 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 house rentals in Shelter Island
Guests agree: These houses 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.
LocationValueAir conditioning

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 in the other, a full bath, outdoor shower hot & cold, an eat-in kitchen. 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.
LocationValuePets

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!
ValueLocationOutdoor spaces

Stylish & Chic w hot tub/ Near Beaches & Village
Stylish Hamptons retreat just minutes from Southampton Village and the area's best beaches. Enjoy a private backyard with a brand-new oversized deck, new outdoor shower, hot tub, fire pit, and sun lounge - perfect after a day at the beach. Cozy up by the indoor fireplace on cooler evenings. Next to Shinnecock Hills Golf Club, 15 minutes from Poxabogue, and close to Wölffer Estate, Duck Walk, Channing Daughters, Scallop Pond Preserve, and Elizabeth A. Morton Wildlife Refuge.
ValueLocationBarbecue

Designer's Dream - Charming Boathouse
An architect's and interior decorator's dream home! This home is a historic boathouse built in the late 1890's with modern updates. In the middle of Greenport Village - walking distance to train station, Jitney stop, and Shelter Island Ferry as well as the best North Fork restaurants, vineyards, bars, and beaches. Two bedroom home with ground floor fireplace, outdoor shower (not enclosed), and beautifully landscaped outside patio w/grilling & dining areas.
FamilyLocationCheckout

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.
LocationValueSleep quality

The Greenport Bungalow
Sweet Modern Bungalow Walking Distance to Town Located in the historic town of Greenport Village - 8 min walk to the beach, center of town, Shelter Island Ferry and LIRR... A newly built sun filled 3 bedroom house with all the amenities you would need when renting a home. Enjoy the large and fenced in back yard after a fun day in this historic Long Island fishing village. Great restaurants, and even better locally produced wine and beer!
ValueLocationCleanliness

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.
LocationFamilyPets

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.
LocationFamilyHospitality

Hamptons - Shelter Island Farmhouse
Kid friendly! Perfect two family split! Come enjoy our island retreat. Relax with the whole family at this peaceful pad. You will be 2 min on bike from Wades Beach. You can also walk to the best BBQ/seafood in Shelter, Commander Codys. Features a large open kitchen/dining room plus also a spacious living room. 4 bedrooms with new mattresses, huge outdoor patio for family BBQs. No dogs please.
ValueFamilyQuiet

Sag Harbor Cottage, Walk to the Beach!
Renovated to perfection, this fully equipped fresh & modern beach cottage has an open-plan living room, dining room & kitchen, all with high ceilings, immaculate finishings, & a sunny lower level TV room. A broad mahogany deck with large outdoor shower & gas BBQ grill runs the full length of the house & overlooks a roomy lawn with great privacy, fire pit and mature landscaping.
ValueLocationCleanliness

Laid Back Relaxation
Kick back and relax in this calm, stylish space. Nice newly updated home on a quiet street within walking distance to beaches, restaurants and a golf course. Great location near Shelter Island heights town, Crescent beach and Sunset beach. The location provides both privacy and relaxation at home with just a short walk or ride to popular Shelter Island spots.
FamilyLocationQuiet
Popular amenities for Shelter Island house rentals
House rentals with a pool

Sag Harbor, Designer w large Pool (3 bed/2.5 bath)
FamilyLocationBeach

Private Oasis W/Stunning Vinyard and Pool Views
LocationValueQuiet

Explore the Water & Woods at a Relaxing Retreat
FamilyLocationWalkability

Oasis backyard, Pool, Gym, and Sunroom!
FamilyValueWalkability

Brand new house with an all year round hot tub.
ValueFamilyLayout

East Hampton Oasis - Pool and Hot Tub
ValueFamilyOutdoor spaces

Luxury Hamptons Home with Heated Saltwater Pool
FamilyValueIndoor spaces

3 BR/Pool. Walk to Beach & Town!
FamilyLocationBeach
Weekly house rentals

Private Hay Beach Retreat with Heated Pool
ValueLocationDecor

Surf Scoter Cottage Shelter Island
LocationFamilyNearby

Newly Renovated w/ Pool, Hot tub & Fireplace
LocationFamilyBackyard

Silver Beach, 3 Bedroom cottage w/ pool
LocationFamilyCheckout

Beautiful Home on Shelter Island
LocationFamilyBiking

Brand New Sun Filled Home
FamilyLocationNearby

Luxury by the Sea!!
LocationValueCheck-in

Greenport walk to beach & vineyard! Brand new home
LocationFamilyHospitality
Private house rentals

Relaxing Spacious House. *pets welcomed*
FamilyLocationDecor

The Saltbox: Outdoor Dining, Fire Pit, Soaking Tub
LocationFamilyDecor

Bayview house with salt water pool & private chef
LocationFamilyView

Luxury Hamptons Poolside Paradise w/ Outdoor Sauna
FamilyLocationLaundry

Southampton Village Escape
FamilyLocationPool

Splendid private cottage
LocationFamilyDecor

Southampton Stunner: Pool, Beach & more!
FamilyLocationBarbecue

Walk to Beach and Greenport Village, Two King Beds
LocationFamilyBiking
When is the best time to visit Shelter Island?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $1,069 NZD | $886 NZD | $996 NZD | $1,018 NZD | $959 NZD | $1,250 NZD | $1,269 NZD | $1,276 NZD | $1,060 NZD | $920 NZD | $933 NZD | $1,018 NZD |
| 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
- New York City Holiday rentals
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- Rentals with pools Shelter Island
- Pet-friendly rentals 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
- Beachfront rentals Shelter Island
- Waterfront rentals Shelter Island
- House rentals Suffolk County
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- House rentals United States
- Yale University
- Mohegan Sun
- Foxwoods Resort Casino
- Cooper's Beach, Southampton
- East Matunuck State Beach
- Fairfield Beach
- Ocean Beach Park
- Charlestown Beach
- Mystic Aquarium
- Southampton Beach
- Sunken Meadow State Park
- Hammonasset Beach State Park
- Soundview Beach
- Powder Ridge Mountain Park & Resort
- Sleeping Giant State Park
- Ocean Beach
- Wölffer Estate Vineyard
- Orient Beach State Park
- Meschutt Beach
- Wesleyan University
- Long Island Aquarium
- Ditch Plains Beach
- Mount Southington Ski Area
- Stonington Vineyards





