Waterfront vacation rentals in Shelter Island

Find and book unique waterfront rentals on Airbnb

Top-rated waterfront rentals in Shelter Island

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

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Superhost

A sandy beach stretches along the Long Island Sound, bordered by greenery. A wooden boardwalk leads to the shore, with lounge chairs positioned for sunbathing. In the background, several buildings are nestled among the trees, completing the tranquil seaside scene.

Condo in North Fork

4.84 out of 5 average rating, 128 reviews

Oceanfront Condo – Incredible Spring Rates!

Overlooking the Long Island Sound, this oceanfront condo is the ultimate escape. Bask in the sun on a private beach or unwind on the waterfront deck with breathtaking views Minutes from the town center, you’ll find local farms, award-winning wineries, gourmet restaurants & charming shops ⚓️ Explore Greenport: A historic seaport with coastal charm & rich culture 🏖 Premium Amenities – Waterfront deck, private balcony, grills, pool, private beach & parking ⛴ Ferry Access to Shelter Island & CT

Guest favorite

A wooden deck area features a dining table with six chairs, accompanied by a grill. A large umbrella provides shade, while the picturesque view of the water and distant marina is visible beyond the railing, set against a clear blue sky.

Bungalow in Hampton Bays

5 out of 5 average rating, 124 reviews

Hamptons Waterfront- Great Location!

My place is right on the water with your own sandy beach. A quick walk to the restaurant and dining. No worries about having a drink and getting home. You’ll love my place because of the location and the ambiance. My place is good for couples, solo adventurers, business travelers, and families (with kids). Note: If this house does not have availability in June, July or August- please check out my other listing also a 2 bdrm/2 bath waterfront house (https://www.airbnb.com/h/canoebeachhousebh).

Guest favorite

A serene view of the ocean stretches across the horizon, framed by wooden railings. Clear blue skies reflect on the calm waters, with distant land visible on the far side. Foliage can be seen along the shoreline, creating a natural border to the expansive vista.

Home in Shoreham

4.86 out of 5 average rating, 104 reviews

Lush Waterview rainforest retreat

The view only gets better in winter. Some of the most awesome sites are during extreme weather. When you’re here it’s like you’re in the middle of the ocean think Perfect storm. Modern Contemporary California style design built into Side of the hill. Over 60 feet of glass looking out at over 180 degrees of spectacular water views. Multi level decks. Privacy in your own oasis. This is not a beach bungalow nor a mansion on a bluff but a domicile one with nature. Uniquely individual paradise.

Guest favorite

Condo in North Fork

4.92 out of 5 average rating, 138 reviews

Beachside Waterview 2Br Condo w/ Pool in Greenport

Relax in a pristine 2Br condo with ocean & pool views. Our remodeled apartment is part of high-end development nestled on LI Sound, just minutes from downtown Greenport. Sip a glass of wine while watching sunset, catch some rays on the beach or deep in the pool. 2 bedroom condo with ocean view, beach, and pool (seasonal) Comfortably sleeps 6 Private beach access year-around Pool (seasonal) Functional kitchenette 2 bathrooms, all toiletries Linens and towels are provided Smart TV AC/Heat

Guest favorite

A spacious outdoor area features a fire pit surrounded by red chairs, with a stone patio providing seating options. A putting green is visible nearby, and the picturesque waterfront is lined with boats and a dock. Lush grass completes the serene landscape.

Home in Mastic Beach

4.93 out of 5 average rating, 121 reviews

Gorgeous Waterfront and Indoor Pool Family Oasis!

Breathtaking Waterfront home with 37 foot heated indoor pool. 3 Bedrooms plus a 800 Sq/Ft master bedroom with wood burning fireplace. WiFi, 3rd floor entertainment room with 120 inch screen movie projector, karaoke, fooseball, pool table. Wraparound terrace, sunroom, 45ft dock with launching ramp, putting green, sand trap, outdoor kitchen, bar & stone patio with tables & BBQ grills & fire pit. Ability to catch abundant fish & blue crabs right from the dock. Picture tells a thousand words.

Top guest favorite

Home in Branford

5 out of 5 average rating, 14 reviews

Breathtaking Panoramic Waterfront

Relax to sweeping views from every room in this unique, 4600 sq foot direct-waterfront home with two small private beaches, boulders by the water, large pool, hot-tub, outdoor bar, kayaks, and fire pit. 2 floors of wraparound patio/deck, plus 3rd floor loft and roof patio. Open floor plan, sweeping staircase, 5 bedrooms plus loft, 3.5 bath plus half bath and outdoor shower by pool. A real oasis! (Note: pool not heated and open mid-may to mid-Oct only; hot tub closed Jan-March)

Guest favorite

Houseboat in North Fork

5 out of 5 average rating, 11 reviews

Peconic River Boatel

Perfectly updated nautical houseboat situated on the scenic Peconic River. Featuring two picturesque bedrooms, a full service eat-in kitchen and a living room with panoramic river view. Enjoy your morning coffee on the outside deck while taking in the sunrise. This historic waterfront town was named to Forbes Advisor’s “Best Places to Travel in 2023” — one of just 11 U.S. destinations on this year’s list. A must see for adventurers and families alike!

Top guest favorite

A wooden deck is showcased, complete with a dining table and chairs, under a large umbrella. Lush green reeds line the waterway, which reflects the cloudy sky. A lamp post and planters with flowers enhance the serene setting, while private docks are visible in the background.

Cottage in Flanders

4.9 out of 5 average rating, 39 reviews

Bayside bliss - Charming 2bdrm on the water w dock

Lovely 2 bedroom cottage located on the water with your own private dock. 2 queen beds, 1 bathroom, and full kitchen. Enjoy a swim and outdoor shower after a blissful kayak along the shores of the Peconic Bay. Easy access to the North and South Forks of Long Island, famous wine trails, Ocean Beaches, and amazing farms. 2 kayaks included in the rental. Experience the food, drink, and beautiful scenery with a short drive to all of the Hamptons.

Guest favorite

An aerial view of a peaceful waterfront cottage surrounded by greenery. The property is situated near a winding river, with visible boat docks and lush vegetation. A private lane is shown leading to the home, emphasizing its secluded location.

Cottage in North Fork

4.98 out of 5 average rating, 44 reviews

Stunning waterfront modern farmhouse with dock.

Relax with the whole family or a group of friends at this peaceful, waterfront cottage. Perfect spot to bring a group for a country retreat in the heart of stunning vineyards, spectacular restaurants and stunning waterscapes. Our home’s interior is beautifully appointed where you will be comfortable both inside and outside on our patio, or deck with a breathtaking waterfront view. Peaceful, relaxing and magical place in an idyllic spot.

Guest favorite

A paved pathway leads toward a private waterfront property, bordered by a white fence and lush greenery. The exterior features light-colored siding, and large windows provide views of the Long Island Sound. The serene atmosphere is enhanced by bright blue skies.

Bungalow in North Fork

4.92 out of 5 average rating, 63 reviews

Incredible Beach Front Bungalow w/ Private Beach!

Experience the very best North Fork has to offer at this beautifully renovated and peaceful private waterfront property. Open sliding doors and step onto a large patio to enjoy panoramic views of the Long Island Sound, and witness the most stunning sunsets! The perfect beach retreat for family and friends or a couple's getaway, one thing for shore is you will absolutely love this charming bungalow!

Guest favorite

An open-concept kitchen and living area feature a modern design. The kitchen includes white subway tile, stainless steel appliances, and wooden stools at the counter. A dining area with a rectangular table and a light fixture above is visible, enhancing the room's spacious feel.

Cottage in Yaphank

4.85 out of 5 average rating, 61 reviews

Beautiful Waterfront Cottage

Historic Waterfront with Private Island (this property has a bridge to a private island). Large south facing deck, brand new kitchen and beautiful antique claw-foot bathtub and rainfall shower. The home is 10 minutes from the beach, 10 min from Bellport, 25 minutes from Southampton and 1 mile from the train station to New York City. Enjoy a quiet escape from the city in this well-appointed home.

Superhost

A light-filled room features a large sliding glass door providing views of Long Island Sound. The serene ocean scene is complemented by a small table set for two and a potted plant, enhancing the inviting atmosphere of this waterfront home.

Home in East Haven

4.8 out of 5 average rating, 143 reviews

Casa al Mare Beachfront Retreat Oceanview

Welcome to Casa al Mare! If you are looking for a place to relax and recharge, look no further. Enjoy this spectacular direct waterfront home while still very close to the city. Yale and downtown New Haven are 15 minutes away. Step out of the glass doors to the patio and walk on the sandy beach! Relax, walk on the sand or swim in Long Island Sound. Stunning water views await you every day.