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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 Fairfield

5 out of 5 average rating, 8 reviews

Newly built twin beach house within steps to beach

Keep it simple at this peaceful and centrally-located home. Newly built in 2019! Premier beach living at its finest. Steps to Fairfield’s beaches and less than a mile to downtown restaurants, shops, and bars. Fenced backyard. Central air throughout. Decks off the front and back with a Weber grill. Furnished with luxury furniture, sheets, comforters, and pillows. Smart TVs in every bedroom and living room. Tesla charging station at the house. Identical home next door available for larger bookings

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, fully updated cottage, 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 harbor 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.

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.

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, 101 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

Guest favourite

Home in Milford

5 out of 5 average rating, 100 reviews

Steps2Beach, Fish Pond w/Tropical Backyard Oasis!

🌟 Special Discounts on Early Birds, Last-Minute Stays & 7+ Nights! 🌴Steps from Walnut Beach & Silver Sands State Park, this guest-favorite escape offers a tropical backyard oasis with a cascading fish pond, multiple lounges, & a seasonal palm tree. Inside, relax in luxury with a gourmet kitchen, elegant furnishings, & modern amenities. Just 90 minutes from NYC, it’s the perfect retreat for beach days, nature adventures, & coastal charm!

Guest favourite

Home in New London

4.95 out of 5 average rating, 132 reviews

House in NL near CGA, Sub Base, Mohegan Casino

House is located in New London CT. Off I95 near Coast Guard Academy 3 mins, Connecticut College 4 mins, Mitchell 11 mins, Navy Base 9 mins,Yale L&M Hospital 10 mins, Branford House Avery Point 15 mins, Ocean Beach 16 mins, Millstone 19 mins, Mohegan 16 mins, Foxwoods 24 mins, Electric Boat 9 mins. Enjoy private house with full kitchen, and dining room for family get together. 20% Discount weekly stay. 35% on monthly stay

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$.

Holiday rentals for every style

Get the amount of space that is right for you

Flats

Convenient locations with everyday essentials

Cottages

Quaint homes, peaceful surroundings

Hotels

Stylish accommodation and amenities

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 Montauk

4.9 out of 5 average rating, 21 reviews

Perfect Montauk Escape Pool Walk to Town and Beach

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 Hampton Bays

4.89 out of 5 average rating, 85 reviews

Perfect Hamptons Summer Rental with Pool

Guest favourite

Home in Fairfield

4.97 out of 5 average rating, 37 reviews

Fairfield! 5 bedroom, 3.5 bath on cul-de-sac

Home in East Hampton

4.94 out of 5 average rating, 16 reviews

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

Weekly house rentals

Home in Hampton Bays

4.78 out of 5 average rating, 99 reviews

Jacuzzi & pool. Fenced in property.

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 Southampton

4.93 out of 5 average rating, 61 reviews

Southampton Quiet Private Home/Pool 6min to Villag

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

Private house rentals

Guest favourite

Home in North Fork

4.88 out of 5 average rating, 123 reviews

The Perfect North Fork Escape

Guest favourite

Home in Sag Harbor

4.95 out of 5 average rating, 93 reviews

Sag village, 4 en-suite BRs, hot tub, beach 5 mins

Guest favourite

Home in Sag Harbor

4.85 out of 5 average rating, 160 reviews

Sag Harbor House for rent.

Home in East Hampton

4.86 out of 5 average rating, 28 reviews

Salt Pool 4 Bed Sanctuary w/ Private Beach Access

Home in Shirley

4.87 out of 5 average rating, 137 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 Montauk

5 out of 5 average rating, 20 reviews

MTK Designer House with huge fireplaces!

Guest favourite

Home in Southampton

4.92 out of 5 average rating, 114 reviews

Serene 3 Bed 2.5 Bath House w/Heated Pool

Quick stats about house rentals in Shelter Island Heights

Total rentals
200 properties
Nightly prices starting at
₹8,661 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