Beachfront holiday rentals in Shelter Island Heights

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Top-rated beachfront rentals in Shelter Island Heights

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Guest favourite

Cottage in North Fork

4.97 out of 5 average rating, 151 reviews

Savor Blazing Ocean Sunsets at a Soothing Beachfront Haven

Newly renovated, 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. Enjoy the designer kitchen with all new appliances, as well as a brand new bathroom, updated bedrooms and outdoor shower. This chic 2-bedroom, 1-bathroom home, which can sleep up to 5, has been designed with an eye for detail, style and relaxation. The master bedroom enjoys a queen sized bed that's perfect for 2 adults. The second bedroom can accommodate up to 3 people with a double bed for two people, and a single bed for one person. Only 80-miles from Manhattan, a 90-minute drive and close to the towns of Jamesport, Southold and Greenport, The Beach Cottage is the perfect summer escape. Stay on the property for swimming, paddle boarding, beach walks and BBQs or venture out to enjoy all the North Fork has to offer. Wine tasting at the French run winery Croteaux, lunch at the world class North Fork Table and Inn, shop at the many Organic Farms or explore the charming historic seaport village of Greenport, all short drives from the cottage. Upon request, Pets are allowed, for an extra fee of $200 per stay. Guests have access the entire property, including a private path to the beach. This stylish retreat is nestled on a private Soundfront beach at the end of a 7-acre property. Wine tasting at Croteaux, lunch at world-class North Fork Table and Inn, and the historic seaport village of Greenport are all within a short drive. The closest Jitney stop is Aquebogue or Riverhead. I am an Australian born designer that lives in NYC and has been renovating homes for the past several years. Our Flatiron loft in NYC was featured in Dwell Magazine, I designed the Upper West Side apartment for the founder & CEO of Soul Cycle, and my husband and I recently renovated our family's weekend beach house on the North Fork. I have a passion for turning houses into homes by bringing the clean, breezy and natural aesthetic, inspired by my homeland in Australia.

Guest favourite

Home in New London

4.89 out of 5 average rating, 9 reviews

Paradise on Pequot

Your waterfront oasis awaits. Offering stunning views of Long Island Sound within walking distance of a private beach, this home has all you are looking for in a seaside getaway. Modern, updated, and with central air, the home includes an open and covered front patio and backyard. Exclusive access to a private beach, the home is also located near Ocean Beach Park, with passes included, offering many daytime and nightly activities for families. Views of four iconic lighthouses are an added bonus!

Top guest favourite

Home in Milford

4.94 out of 5 average rating, 137 reviews

#2 Milford Beach (across street) Charles Isle 2BR

Welcome to your perfect Milford beachfront escape! This beautifully furnished 2-bedroom, 1-bath 2nd floor unit sits directly across from the beach, with beautiful water views. Just 100 yards from Silver Sands State Park, you’ll have easy access to its beaches, nature trails, and famous boardwalk. This unit offers beach gear, private yard for sunset dining, and proximity to Milford’s lively downtown. Whether here for a romantic getaway or family retreat, this spot offers relaxation or adventure!

Superhost

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.

Superhost

Cottage in Milford

4.78 out of 5 average rating, 32 reviews

Cheerful 2 bedroom cottage on beach

Take it easy at this unique and tranquil getaway with friends or family. Located on Cedar beach, this quiet original 2 story 1915 home is the perfect place to sit back, relax and remember the good ol’ days. Enjoy the private beach and views. Property has off street parking for 2 small cars and public street parking only a block away. AC window units, office, WiFi, coffee bar and tv w/Roku (guest to login.)Master bed has private balcony overlooks yard to beach. This is rear house on property.

Superhost

Cabin in Shirley

4.87 out of 5 average rating, 153 reviews

A-Frame cabin with private beach & epic sunsets

Just a 1.5 hour drive from NYC, this home is the perfect beach getaway spot, with a few steps from the deck to the private beach with its beautiful view across the Great South Bay. Remote work with stunning water views through the wall of windows & in cold weather light a fire while sunlight floods the living space. Two queen bedrooms & bunk bed room sleeps 6 guests, great for families or a small gathering of friends. 5 min drive to ocean beach with great swimming & surfing at Smith Point.

Guest favourite

Home in Milford

4.96 out of 5 average rating, 210 reviews

Designer Beach Retreat on Exclusive Cedar Beach

Welcome to your own slice of heaven! Enjoy dinner in your Chef's kitchen while watching one of the most radiant sunsets you will ever see. Stunning views from the private rear deck or snuggled on the couch inside the living room. Wade into Long Island Sound with semi-private beach access 250 feet away. The property is 5 doors down from the CT Audubon Society, known for its epic views and wildlife watching. The sunrises & sunsets are beautiful! 15 minutes to Yale. We can't wait to host you!

Superhost

Flat in Ocean Beach

4.8 out of 5 average rating, 5 reviews

2BR Apartment with Terrace

This modernized two bedroom apartment with terrace views of the bay offers a perfect blend of comfort, convenience, and coastal allure. Equipped with a fully stocked kitchen, Smart TV, WiFi and washer/dryer. Three Beach chairs and umbrella. Sleeps 5 comfortably with 3 twin beds and 1 full bed. Located steps away from an array of restaurants, bars, and shops, with the beach just a 5-minute stroll away. Don't miss out on this perfect coastal retreat – book now for an unforgettable vacation!

Guest favourite

Home in Woodmont

4.98 out of 5 average rating, 43 reviews

Beachfront paradise- come, stay, relax!

Looking for an island-feel getaway? You've arrived! Welcome to La Spiaggia. Come enjoy this 4 bedroom, 2 bath home and wake up to the sound of waves crashing on your private beach. Have a cup of coffee watching the beautiful sunrise, work from home on the oversized front porch, and enjoy the evening with beautiful lighting and sunset views. Take a stroll along the ocean to Bay View Beach, or simply relax and take in the expansive oceanfront views. Soak up the summer sun at La Spiaggia!

Top guest favourite

Home in Woodmont

4.96 out of 5 average rating, 24 reviews

La Sirena Beach Cottage

Charming Milford Bayview Beach cottage. The perfect blend of coastal charm and comfort. Boasting 3 cozy bedrooms and an inviting outdoor space. You'll have a comfortable place to relax and unwind inside or out. Yet the real gem is our location -- just a short 2-minute walk to the beach, where you can soak up the sun, ride the waves or take a leisurely stroll along the shore. Whether you're seeking a romantic escape or a family vacation this cottage is tailored to meet your needs!

Guest favourite

Home in Milford

5 out of 5 average rating, 5 reviews

Seaside Paradise

Welcome to our beach house in Milford! This getaway is just a short walk from the beach, making it the perfect vacation spot for families or groups of friends. Whether you're looking to soak up the sun on the sandy shores, explore the charming town of Milford, or simply relax in a comfortable beach house, our rental is the perfect choice. We can't wait to host you and make your beach vacation unforgettable. Book now and start counting down the days until your beachside getaway!

Guest favourite

Flat in Montauk

4.86 out of 5 average rating, 111 reviews

Recharge at our Renovated ocean front unit

Looking for a relaxing weekend to recharge on the beach? Then this newly renovated, bohemian-chic, apartment is perfect for you. Imagine waking up every morning to beautiful unobstructed ocean views and ending your night with a drink in hand watching the sunset. If you’re lucky, you might see some whales or dolphins breaching in the water right off our private beach. We would love to host you for your Montauk beach getaway.