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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Guest favorite

Home in Branford

5 out of 5 average rating, 7 reviews

Breathtaking Panoramic Waterfront

Relax to sweeping views from every room in this unique, 4600 sq foot curved custom-built, direct-waterfront, home. Amazing location with water on three sides, two small private beaches, boulders by the water, large pool, hot-tub, outdoor bar, pier, kayaks, boat house, and fire pit. 2 floors of wraparound patio/deck, plus 3rd floor rooftop. Open floor plan, sweeping staircase, 5 bedrooms plus loft. So much to do and enjoy in this waterfront oasis! (Pool not heated; pool closed after mid Oct.)

Guest favorite

Home in East Haven

4.96 out of 5 average rating, 131 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

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

Condo in North Fork

4.92 out of 5 average rating, 137 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

Home in Hampton Bays

5 out of 5 average rating, 19 reviews

Hamptons Waterfront Getaway

Take a break and unwind at this peaceful oasis. Welcome to waterfront living in this beautifully renovated 4 bedroom, 2 bath home situated on .75 acre, adjacent to a marina. You'll be blown away by the unobstructed 180-degree water views over Shinnecock Bay all the way to the inlet. The main feature of this home is the wall-to-wall glass in the living room and dining area, offering panoramic views of the bay. The back two decks are the perfect spots for outdoor dining and relaxation.

Guest favorite

Home in Westhampton Beach

4.96 out of 5 average rating, 25 reviews

Dune Rd Village Waterfront Private Beach Access

Look no further for the perfect stay that offers an amazing location and sunset views, this stylish beach house is waterfront on Dune Road, Village of Westhampton Beach. The 1.2 acre property is located right on the bay with deep water dock and private boardwalk ocean beach access. 4 BR and 3 full BA, balcony and water views from each room. The home comes ready with high end furnishings by Hildreth's, Restoration Hardware, Serena & Lily, and Pottery Barn. Home come well stocked.

Superhost

Condo in North Fork

4.83 out of 5 average rating, 123 reviews

Seaside Escape w Pool, Private Beach + Patio

Located on a small bluff overlooking the Long Island Sound… Bask in the sun on our private beach. Just minutes away from the town’s center, discover farms, wineries, restaurants & shops. On the North Fork, farmland and wineries unroll all the way to the ocean. ⚓️ Greenport is a historic seaport located on Long Island's North Fork. 🏖 Waterfront private deck, balcony, grills, private beach, pool, parking ⛴ Ferry access to the South Fork, Shelter Island & Connecticut

Guest favorite

Condo in North Fork

5 out of 5 average rating, 107 reviews

"Breathtaking Waterfront Water's Edge view"

" Breathtaking Waterfront Water's Edge condominium. Newly renovated! Relax and enjoy this beautiful, luxurious space. Suite B-204 accommodates 6 guests very comfortably. Two bedrooms, two bathrooms, living room with sofa (pull-out bed), kitchen area, eating area with chairs- all newly renovated. Located on the North Fork of Long Island, Cliffside Resort Condominiums in Greenport, New York." So many activities to choose from nearby and in the quaint village of Greenport!

Guest favorite

Houseboat in North Fork

5 out of 5 average rating, 10 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!

Guest favorite

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

Cottage in North Fork

4.98 out of 5 average rating, 43 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.

Superhost

Home in North Fork

4.9 out of 5 average rating, 200 reviews

Greenport Beach House

Nestled steps from the beach, and all that Greenport and the North Fork has to offer, this exquisitely charming 3 bedroom 2 bathroom waterfront home is absolutely delightful.. You’ll love my place because of the views, the location, the people, the ambiance, the outdoors space, and the Saltwater pool.. My place is good for couples, solo adventurers, business travelers, families (with kids), groups, and furry friends (pets).