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House holiday rentals in Shelter Island Heights

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Top-rated house rentals in Shelter Island Heights

Guests agree: these houses are highly rated for location, cleanliness and more.

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Home in Woodmont

4.92 out of 5 average rating, 26 reviews

Light-filled Beach House Steps from the Sand

Located in prime Bayview Beach, a one min stroll to the sandiest beach in Milford. Two floors with private patio. Main level: half-bath, Cooks kitchen with a 6 person dining area, living room with flatscreen. Upstairs: master w/king size bed & en-suite bath, kids bedroom w/ bunkbed, another full bath w/ tub. 3rd bedroom with queen bed and trundle twin. If you want a get-a-way from the city, or just an escape then come to this tucked-away home. Enjoy all that this coastline gem has to offer.

Guest favourite

Home in North Fork

5 out of 5 average rating, 9 reviews

Stylish Beach Getaway: pool & walking location

Perfectly located within walking distance to shops, beaches, and restaurants, our designer home offers comfort, luxury amenities, and privacy. Interested in a long term rental? Message us! Enjoy a beautifully landscaped backyard with pool, chefs kitchen for hosting, and nearby beach farms & wineries. Bedrooms boast organic linens and bathrooms offer Bathing Culture products. Kitchen is stocked with local organic pantry staples and stainless steel appliances to cook or grill on the patio.

Guest favourite

Home in East Hampton

4.95 out of 5 average rating, 228 reviews

Private beach Historical House with large property

Entire three-story house. 3 large bedrooms and 3 full baths on a very private, 2+acre wooded lot on the bay in Historical East Hampton with private beach access. Fully renovated in 2018 with modern amenities while preserving the original charm. A/C and heating. Private upper floor with bedroom + sitting area for office and extra sleeping. Modern kitchen with island that opens to living room with fireplace. Walk through the secluded backyard to enjoy the amazing sunsets. Ideal for fishing.

Guest favourite

Home in North Fork

4.98 out of 5 average rating, 100 reviews

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, and recently & lovingly fully renovated and restored. 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.

Guest favourite

Home in Hampton Bays

4.92 out of 5 average rating, 119 reviews

Hamptons "Get Away" Near Beach/Wineries/Golf

Located in Hampton Bays-the heart of The Hamptons surrounded by water! Close to beaches, waterfront restaurants, wineries, golf & wedding venues. Open floor plan w/ modern flair. 4 bedrooms, 2 full baths, eat-in kitchen, spacious living room and lower level recreation area/ foosball. Enjoy amenities including smart TVs/appliances, EV Charger, 2 fireplaces, 1Gb WiFi, large deck w/ string lites, BBQ, firepit, & outdoor shower. Great for families, couples, coworkers and friends!

Guest favourite

Home in Stonington

4.98 out of 5 average rating, 162 reviews

Historic charm & modern luxury in downtown Mystic

We are long-time AirBNB guests who have tried to create the home we are always looking to book -- family friendly with modern amenities. Open floor plan on the main level, new heat and air con throughout the house, three bedrooms and family bathroom on the second floor. Art supplies, toys and children's books all ready for you as well as a pack n play and booster seat. Backyard oasis with pergola, walking distance to drawbridge. Pets considered on a case by case basis.

Home in Westhampton Beach

5 out of 5 average rating, 4 reviews

Summer Main Home plus cottage close to Main Street

Come relax and enjoy! Beautifully updated Main home with separate cottage. Perfect for in-laws and guests. Each home has its own kitchen, living space, washer/dryer, and outdoor seating. Main house: 4 Br, 3 ba Cottage: 2 Br, 1 ba Outdoor shower for an after beach rinse, 2 patios, pergola, hammock, bbq. A two person kayak available for use; beach passes included. Games, internet, tv... Walk to coffee shops, restaurants, worship, and marina. Bike to beach.

Guest favourite

Home in Montauk

4.99 out of 5 average rating, 100 reviews

6 minute walk to Ditch Plains Beach

IMPORTANT: From Memorial Day 2024 - Labor Day 2024: weekly (1 week/2 week/3 week rentals must start and end on Saturdays. Monthly rentals can start on the first of the month regardless of the day of the week. Great beach house close to Ditch Plains beach with 3 bedrooms and 2 bathrooms. 2 queen beds and 2 bunk beds, deck, barbecue, outside shower, huge yard, recreation room. Spend your days at the beach and grill at night. Wifi, tv, and outdoor fire pit.

Guest favourite

Home in Groton

4.85 out of 5 average rating, 13 reviews

The Blair Durgin House in Mystic

The Blair Durgin House c 1899 , luxury apartments in newly renovated home. This location in Willow Point with water views and it’s less than a mile to downtown Mystic. You can enjoy the entire house, first floor apt has 3 bedrooms and 1 bath with full kitchen. Second floor apt has 3 bedrooms 2.5 bathrooms full kitchen. The entire house is available for family reunions or large groups of family and friends. Pick your dates you will not be disappointed .

Guest favourite

Home in Montauk

5 out of 5 average rating, 6 reviews

Hilltop Bright Home w/New Pool Summer 2024

Home is professionally managed by Montauk Rental Management Group. Your family will be close to everything when you stay at this centrally-located Montauk home. Short drive to Town and Beaches. This home was recently painted and updated, it's clean, bright and the perfect family rental! -4 bedrooms -3 bathrooms -Spacious deck with water views -Outdoor dining & seating -Grill -Peaceful, quiet location perched on a hill Rental Registry 23-780

Home in Shelter Island

4.9 out of 5 average rating, 115 reviews

Hay Beach Getaway!

Welcome to our family-friendly oasis just two blocks from beautiful beaches! Our house offers an open space living area, an expansive yard, fire pits, and a basement with a playroom and workout area. Enjoy our quiet neighborhood. We provide kid-friendly toys, beach gear, bicycles, and more. Sleeps six, with additional options available for larger parties. Cleaning fees for winter stays are 0$.

Guest favourite

Home in North Fork

4.98 out of 5 average rating, 175 reviews

Greenport Village walking distance to all

Large spacious home in the heart of wine country. Roomy den for relaxing after the wineries. Screened in patio for al fresco dining and enjoying the spacious yard. Hot tub operational year round! Strong, fast wifi with multiple extenders. Message me with any questions or for special offers on 4/5 day stays or midweek 2/3 night specials.

Holiday rentals for every style

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Popular amenities for house rentals in Shelter Island Heights

Free parking on premises

Air conditioning

House rentals with a pool

Guest favourite

Home in Amagansett

4.95 out of 5 average rating, 40 reviews

Wonderful Amagansett Home - Bay View & Heated Pool

Guest favourite

Home in East Hampton

4.87 out of 5 average rating, 103 reviews

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

Guest favourite

Home in East Hampton

5 out of 5 average rating, 36 reviews

Stunning Central E. Hampton Home w/ gunite pool.

Guest favourite

Home in East Hampton

5 out of 5 average rating, 5 reviews

The Hideaway

Guest favourite

Home in North Fork

5 out of 5 average rating, 10 reviews

Long Island home w/ large pool

Guest favourite

Home in Hampton Bays

4.89 out of 5 average rating, 85 reviews

Perfect Hamptons Summer Rental with Pool

Home in East Hampton

4.94 out of 5 average rating, 16 reviews

Walk to Water. Stunning Home with Gorgeous Pool & Grounds.

Guest favourite

Home in Mastic Beach

4.93 out of 5 average rating, 120 reviews

Gorgeous Waterfront and Indoor Pool Family Oasis!

Weekly house rentals

Guest favourite

Home in Water Mill

4.92 out of 5 average rating, 125 reviews

Beach Barn w/ Sauna and Heated Pool - Dog Friendly

Guest favourite

Home in North Fork

4.97 out of 5 average rating, 247 reviews

The Greenport Bungalow

Guest favourite

Home in Montauk

5 out of 5 average rating, 20 reviews

Montauk beach house!

Guest favourite

Home in Shelter Island

5 out of 5 average rating, 29 reviews

Family Friendly Oasis Steps to Water - Heated Pool

Guest favourite

Home in North Fork

4.93 out of 5 average rating, 107 reviews

Maritime Village Getaway with Backyard

Guest favourite

Home in East Lyme

4.96 out of 5 average rating, 184 reviews

Beachfront Paradise

Guest favourite

Home in Madison

4.87 out of 5 average rating, 23 reviews

Historic Beachside Glamour

Guest favourite

Home in North Fork

4.95 out of 5 average rating, 38 reviews

Water Views Beach Greenport Getaway

Private house rentals

Home in East Hampton

4.86 out of 5 average rating, 28 reviews

Salt Pool 4 Bed Sanctuary w/ Private Beach Access

Guest favourite

Home in Shirley

4.9 out of 5 average rating, 136 reviews

Cope near the beach

Guest favourite

Home in Water Mill

4.99 out of 5 average rating, 84 reviews

Pristine 5 bedroom Home - South of the Highway

Guest favourite

Home in North Fork

4.91 out of 5 average rating, 11 reviews

Private Beach access along the Wine Trail

Guest favourite

Home in East Hampton

4.92 out of 5 average rating, 144 reviews

Heated pool, games room, near beach, kid-friendly

Guest favourite

Home in Montauk

4.71 out of 5 average rating, 21 reviews

The Raffle Beach House

Guest favourite

Home in East Hampton

4.97 out of 5 average rating, 31 reviews

Designer Waterfront Cottage on Gerard Dr

Home in Southampton

5 out of 5 average rating, 6 reviews

Hygge House-Danish for comfort contentment cozy

Quick stats about house rentals in Shelter Island Heights

Total rentals
200 properties
Nightly prices starting at
₹8,663 before taxes and fees
Total number of reviews
5.9K reviews
Family-friendly rentals
180 properties are a good fit for families
Pet-friendly rentals
80 properties allow pets
Rentals with a pool
70 properties have a pool

Destinations to explore