Beachfront vacation rentals in Shelter Island

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Top-rated beachfront rentals in Shelter Island

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Guest favorite

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 favorite

Home in East Haven

4.97 out of 5 average rating, 146 reviews

The Breakaway - a waterfront gem.

Located next to historic Lighthouse Park, this Morgan Point, California-style bungalow overlooks a lighthouse and breakwater that protect New Haven Harbor. Prepare oceanfront dinners in your modern kitchen; relax to sunrises, sunsets, & the sound of waves. A quiet beach is steps from the door for swimming and kayaking. New Haven sights, restaurants, & nightlife are only minutes away. Picturesque coastline communities, local vineyards, breweries, fall foliage, & commuter rail to NYC are nearby.

Guest favorite

Home in North Fork

4.9 out of 5 average rating, 21 reviews

The Sandy Shack - Coastal Escape

Escape to your own private oasis at this charming beach house in Greenport. This beachfront home offers views of the ocean in every room. Inside, the living space gives plenty of natural light and sitting areas. The kitchen has everything you need to cook for family & friends. There are 4 beds to choose from, which can sleep 6 total. Outside, enjoy your own private beach as well as kayaks to use at your leisure. Located next to Greenport's best restaurants and wineries, book your stay today!

Guest favorite

Home in New Haven

4.95 out of 5 average rating, 108 reviews

Beach Haven - waterfront, near Yale, sunsets

Everything you need for an amazing vacation, year-round, in our comfortable home right on the beach! Walk out the back door and dip your toes in the sand and in Long Island Sound. Enjoy spectacular views from the back patio, sun room, and most rooms in the house. Watch the sunset while soaking in the hot tub. Sit by the gas fireplace with a book. Stroll along the lovely nearby sea wall. 10-minute drive to Yale and all downtown New Haven has to offer. 5-minute drive to Lighthouse Point Park.

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 favorite

Condo in Montauk

4.83 out of 5 average rating, 176 reviews

Coastline View Studio

This sun drenched studio apartment is perfect for families, couples or friends looking to get away and discover Montauk! Located in Montauk's harbor district. This unit is perfectly located to experience all that Montauk has to offer... Sit back on the balcony and enjoy a glass of wine as the sun sets perfectly over Culloden Point. A short walk to the Harbor, the Dock, Gosmans, TTs, Salivars, Sunday Funday, Fisher's, La Fin, Viking Fleet (fishing, Whale watching & Ferry).

Guest favorite

Home in East Lyme

5 out of 5 average rating, 7 reviews

3 Houses Off the Water-Private Black Point Beach

Newly furnished, 4 bedroom beach house steps away from Black Point Beach with lots to do for the family! Private playground, basketball, tennis courts and more… The neighborhood even has its own market, a 5 minute walk! Niantic offers great restaurants, including Sift bakery, shops, children’s museum and boardwalk. A short drive to Mohegan Sun, Rocky Neck, Mystic and the Ferry to Block Island! Don’t miss your opportunity to rent this charming home!

Top guest favorite

Apartment in Montauk

5 out of 5 average rating, 8 reviews

Oceanfront Corner Studio Bungalow on the beach

Kick back and relax in this calm, stylish space and listen to the waves. Best rental unit in entire resort. Corner oceanfront studio, 700 sq feet with 1500 sq ft private patio with ocean and dune views, outdoor bbq, with outdoor dining table. Kitchen has a full size fridge and dishwasher. queen bed and queen size pull out sofa accommodates 4. Resort Property includes heated pool, tennis courts, gym, beach with towels, umbrellas and chairs.

Guest favorite

Apartment 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.

Guest favorite

Home in East Haven

4.94 out of 5 average rating, 52 reviews

Spectacular Waterfront Home on Private Sandy Beach

Beautiful two bedroom home located directly on the widest private beach in Connecticut is the perfect location for your next vacation. Newly built, this house has hardwood floors throughout, brand new appliances, washer and dryer, queen bed, two twin beds, fully furnished- including all kitchen necessities, central air, two decks, gas grill, plenty of parking, beach chairs, toys, kayak, paddle board, life vests, etc.

Superhost

Apartment in Montauk

4.84 out of 5 average rating, 152 reviews

MONTAUK OCEAN FRONT!

Charming oceanfront Montauk locale with perfect proximity to all town activities! Fall asleep to the lull of ocean waves. Ocean view and steps to the sand and town! New kitchen, Queen bedroom,Queen sofabed in living area, new rain shower bathroom, plus a large front deck for al fresco dining! Perfect for families, and a girls weekend!

Guest favorite

Apartment in North Fork

4.88 out of 5 average rating, 8 reviews

Beach House - Apt 2

The Beach House - apt 1 is a 650 sq foot alcove studio apartment, less than 500 feet from the beach. Fully renovated with an open layout and modern rustic style. It has updated appliances and a large smart tv. There is a cute restaurant conveniently located next door. First floor. The patio and backyard area are shared.