Beachfront vacation rentals in Shelter Island Heights

4.88 out of 5 average rating, 154 reviews

A living room features a light-colored sofa against a neutral wall, complemented by a striped area rug. A wall-mounted TV and decorative elements, including a mirror and wall hooks, enhance the space. Soft lighting is provided by two standing lamps, creating a welcoming environment.

Condo in North Fork

Waterfront Autumn Escape in Wine Country: 2BR

Overlooking the Long Island Sound, this oceanfront condo is the ultimate escape. Bask in the sun on your 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

A serene sunset is captured over the bay, with warm hues reflecting on the water's surface. Silhouettes of wooden posts emerge from the calm waves, creating a tranquil atmosphere. The horizon showcases a mix of colors as the day transitions to evening.

4.95 out of 5 average rating, 248 reviews

Private beach, fully updated house, 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 bayside 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.

4.89 out of 5 average rating, 241 reviews

The exterior of a two-story beach cottage is visible, featuring a soft gray facade and a balcony on the upper level. Large windows illuminate the lower floor, surrounded by a well-kept lawn and garden. A decorative trellis adds character to the welcoming entryway.

Home in East Haven

Beach Cottage by the Sea

Beautiful 1920's beach cottage with beach access just across the street. Enjoy the sea breeze, ocean views, and sound of the waves lapping in this quaint home with unique architecture. Ten minutes to downtown New Haven and Yale for great places to eat, museums, and nightlife. Public beach and playground nearby. Warm and welcoming community. Master bedroom has vaulted ceilings and deck with views of the sea. Central Air, Cable TV, outdoor grill, plenty of parking. Enjoy this lovely home!

4.95 out of 5 average rating, 124 reviews

A vibrant sunset reflects on calm waters, with shades of orange and purple illuminating the sky. Silhouettes of small boats are visible along the sandy shoreline, while gentle waves create a serene atmosphere. The scene offers a tranquil view of Long Island Sound at dusk.

Home in East Shore

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.

4.91 out of 5 average rating, 149 reviews

Two blue Adirondack chairs are positioned on a manicured lawn, facing a vibrant sunset over the ocean. The sky displays pink and orange hues as the sun sets on the horizon, creating a serene outdoor setting.

Condo in North Fork

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

A serene waterfront view features a sailboat gliding across calm waters. Lush green grass borders the shoreline, reflecting the tranquility of the environment. The clear blue sky stretches overhead, enhancing the peaceful atmosphere of the setting.

5 out of 5 average rating, 138 reviews

Hamptons Waterfront- Great Location- On the bay

Amazing Beachfront vacation home located directly on a private sandy beach on Shinnecock Bay. Stunning waterfront views- sunrises/sunsets. Have a bbq and relax right on the back deck and watch the boats pass by or take a quick walk or shuttle boat to some of the Hamptons best restaurants. 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).

4.98 out of 5 average rating, 167 reviews

A light-filled living space is highlighted by a wall of glass, providing expansive views of the water and a natural landscape. The space includes a round coffee table on a light floor, with comfortable seating arranged to enjoy the serene outdoor scenery.

Cottage in North Fork

Savor Ocean Sunsets at a Soothing Beachfront Haven

Newly renovated and featured as a top Airbnb by New York Magazine, 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. Stay on the property for swimming, beach walks, sunsets and BBQs - or venture out to enjoy all the North Fork has to offer.

4.98 out of 5 average rating, 191 reviews

An open-concept kitchen and living space features modern appliances and a wood-topped island with seating for three. Light cabinets and blue walls create a bright environment, while a hallway visible in the background leads to the entrance of the cottage.

Home in Branford

“The Lighthouse” A Beach Cottage by the Sea!

Relax at this unique and tranquil getaway. Long Island Sound to the left, hiking trails to the right. Come kick your feet up at this quiet dead-end road. Enjoy all the modern amenities in this gem of a cottage community. Restaurants and nightlife are just a quick stroll away. Avoid roadside hotels and take a vacation for a night, week, or longer! Check in anytime and at your convenience!No keys to lose or to return! This property provides secure, keyless entry with an August Smart Lock!

5 out of 5 average rating, 104 reviews

A lush backyard features a children's playset alongside a hammock. Adirondack chairs are arranged around a fire-pit, framed by trees and greenery. A serene waterfront view is visible, with a dock extending into the calm waters, enhancing the natural landscape.

Villa in The Hamptons

Hamptons WaterLiving-Dock, Kayak, Beach, EV charge

[FOLLOW US on INSTA @29watersedge] 1-mile from the beach, this child-friendly waterfront Southampton home is a perfect family getaway. Ready for watersports: kayak, paddleboard, boat, or jet ski. Walk down to the beach for a swim in the bay. At home, the backyard has it all: large dock, fire pit, swing/playset, hammock, grill, & oversized deck to take in the views. Surrounded by nature and water, you are just minutes from restaurants and shopping in Southampton Village &Sag Harbor.

4.99 out of 5 average rating, 107 reviews

An aerial view captures a cozy cottage surrounded by lush greenery, featuring large windows that glow warmly in the evening light. A stone patio is visible, with outdoor seating and a fire pit. Nearby, a well-maintained lawn and a parking area with vehicles can be seen.

Cottage in Guilford

Waterfront Joshua Cove Cottage with private beach.

Beautiful architecturally designed 1 Bedroom + loft Cottage on Joshua Cove in Guilford. The sunsets are spectacular from your own private beach. Enjoy Fall Foliage, swimming, fishing, and some of the best Kayaking from this perfect setting. Minutes from the Guilford train station, restaurants, shopping, and historic town green. The property is just 15 minutes from New Haven, and the Yale campus. The Thimble Island cruise, and the Ct. river steam train/cruise are nearby as well.

A dining set featuring a large wooden table with eight matching chairs is positioned under a spacious umbrella, offering shade. Lush greenery and a serene waterfront view are visible nearby, providing a peaceful outdoor setting.

4.98 out of 5 average rating, 104 reviews

Breezy Waterfront Home With private Dock

This charming waterfront home is the ideal getaway for the active family with the Hamptons' largest natural 'saline pool' (the Peconic Bay) just footsteps away. This home easily sleeps 7 - with 3 bedrooms and 3 separate kids' sleeping cabins. You can jump on our standup paddle board right off our private dock, jog along wide stretches of pebble beach, have a swim race to our floating swim platform or simply relax in the hammock. 2 bathrooms indoors and 1 private outdoor shower,

4.93 out of 5 average rating, 136 reviews

Home in Clinton

PRIVATE BEACH: ROYAL OCEANVIEW CASTLE @ CLINTON

INSTANT BOOK: Apr 2026 - Jan 2027 All Dates Open Availability ALL SUMMER '2026: June + July + Aug Available to Instant Book Steps away from CT Shoreline in back of beach house! Amazing Views - Waterfront Outdoor Deck w/ Seating (2nd week May - until Nov 6th) *certain holidays/summer excluded in booking minimums *discounts applied to nightly rate only *we can not combine multiple discounts, yet highest % will apply *if available, also apply 10% non-refundable booking option

Popular amenities for Shelter Island Heights beachfront rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly beachfront home rentals

4.85 out of 5 average rating, 52 reviews

A beachfront view captures a private sandy beach with an outdoor umbrella and seating area. The chic living room features large windows overlooking the sea, showcasing light neutral tones and plush seating. A glimpse of a cozy bedroom reveals inviting furnishings and bright accents.

Home in Westbrook

Duckling Crossing | Beach House on the Sand

4.96 out of 5 average rating, 47 reviews

A serene waterfront scene is presented, showcasing calm blue waters extending towards the horizon under a clear sky sprinkled with a few clouds. The sandy shoreline gently curves along the edge, bordered by sparse greenery for a peaceful coastal ambiance.

Home in Mastic Beach

Mastic Beach Surf House

5 out of 5 average rating, 25 reviews

A spacious great room is highlighted by a cathedral ceiling with exposed wooden beams. Comfortable sofas frame a central coffee table, while large windows provide natural light, accentuated by sheer white curtains. A cozy reading nook is positioned against the wall, complemented by a variety of books.

Cottage in North Fork

Lovely North Fork Beach Cottage (2 BR/2 bath)!

5 out of 5 average rating, 35 reviews

A view of the exterior of the blue house, showcasing a white lattice railing along the patio. Steps lead down to the water, with a calm blue surface reflecting the sky. Potted plants add a touch of greenery to the space.

Home in Guilford

Charming 2BR Beach House, Overlooking the Water

4.94 out of 5 average rating, 159 reviews

A well-maintained putting green is positioned in the front yard, surrounded by soft turf and bordered by gravel. Small flags are placed on the green, with nearby shrubs and trees adding to the outdoor landscape. The house is visible in the background.

Home in Shirley

Beach Waterview, 3 KING Beds, Golf Putting Green

4.95 out of 5 average rating, 75 reviews

A bright sleeping area is furnished with a queen bed, complemented by soft bedding and decorative pillows. Natural light fills the space through two small windows, with an antique mirror and a lamp providing additional lighting. A small seating area is visible to the side.

Cottage in North Fork

Beach Cottage 3 | New Suffolk | Northfork

4.75 out of 5 average rating, 8 reviews

Home in Guilford

Guilford Beach Cottage

5 out of 5 average rating, 43 reviews

A serene waterside view is presented from the deck, showcasing the calm waters, dotted with small boats. Rocky shorelines and lush greenery line the opposite bank, under a clear blue sky. A patio area with chairs can be seen below the deck.

Cottage in Guilford

Waterfront Cottage With Unforgettable Views

Beachfront home rentals with a pool

5 out of 5 average rating, 16 reviews

A serene outdoor area features a heated saltwater pool surrounded by well-manicured grass. Two lounge chairs are positioned nearby, providing a perfect spot for relaxation. The house is visible to the left, with a deck leading to the pool, framed by lush trees.

Home in Brookhaven

Beautiful 2 acres, 3 Bd /2 b, Pool, Pets Welcome

An indoor heated pool is surrounded by elegant wood paneling and framed artwork. Natural light filters through the windows, reflecting off the water's surface. A cozy sitting area is positioned nearby, offering a relaxing space adjacent to the pool.

4.9 out of 5 average rating, 81 reviews

Lovely Year Round Vacation Home in the Hamptons

4.8 out of 5 average rating, 25 reviews

A bright and airy living space is highlighted by skylights and white wooden beams. A spacious kitchenette is situated behind a dining table surrounded by light chairs. Large windows invite natural light, and a television sits on a white console between soothing tones of gray and cream.

Condo in The Hamptons

Waterfront Elevated Bungalow - Spectacular Views

The beach house features a spacious second-level deck with ample seating and views of the surroundings. Large glass doors provide access to the yard, which is bordered by a grassy area and includes a hot tub. The exterior showcases modern architecture with light-colored siding.

4.92 out of 5 average rating, 13 reviews

Montauk 4bd/3.5ba Ocean, pool spa & private beach.

4.83 out of 5 average rating, 29 reviews

The image presents a coastal view featuring a well-maintained property adjacent to the shoreline. The sky displays a gradient of colors at sunset, and gentle waves can be seen lapping against the rocky beach. Surrounding greenery complements the tranquil setting.

Home in North Fork

North Fork Sound Front Home with Pool

A spacious kitchen is featured with white cabinetry and a large island topped with light-colored stone. Four black bar stools are positioned at the island. The area is brightened by natural light from windows, highlighting modern appliances and decorative touches like a bowl of fresh flowers.

4.56 out of 5 average rating, 50 reviews

Steps to the Ocean, Bayside Tranquility, W/Pool!

4.88 out of 5 average rating, 8 reviews

Home in Brookhaven

Brookhaven Design Retreat w/ Pool

4.88 out of 5 average rating, 103 reviews

The living area showcases a comfortable sofa adorned with decorative cushions, complemented by a coffee table. A kitchen area with modern appliances is visible, alongside a dining cart. Art pieces frame the walls, and natural light enters through sliding glass doors.

Condo in North Fork

Waterfront Condo C-204 at The Cliffside Resort

Private beachfront home rentals

A dining area is arranged with a wooden table and eight white chairs, framed by large windows showing expansive views of the inlet and surrounding nature. A pendant light hangs elegantly above the table, adding a focal point to the serene setting.

5 out of 5 average rating, 37 reviews

Tranquility at the Water’s Edge

A vibrant sunset is visible through a window, casting a warm light over a calm bay. The sun reflects on the water, and silhouettes of trees frame the scene, creating a serene coastal atmosphere.

4.95 out of 5 average rating, 100 reviews

Stunning Bay-front Views - Hampton Bays

4.92 out of 5 average rating, 61 reviews

A spacious outdoor deck overlooks the tranquil waters of Long Island Sound, featuring comfortable lounge seating and a fire pit. The serene beach is visible in the background, framed by lush greenery, inviting relaxation and outdoor gatherings under the open sky.

Home in Morgan Point

Oceanfront Getaway - Quiet, Firepit + Pvt Beach

A light-colored boat is anchored in calm water, surrounded by lush greenery. Reflections of the boat can be seen on the still surface, while distant homes are visible along the shoreline under a clear blue sky.

Cottage in The Hamptons

4.87 out of 5 average rating, 91 reviews

Waterfront Beach Home & Garden —AC, BBQ, Kayaks!

4.96 out of 5 average rating, 24 reviews

A large beach house is visible, featuring multiple gables and a spacious deck with balcony. The facade is painted in light grey, complemented by white trim. In the foreground, sandy beach leads toward the house, framed by green grass and shrubs on either side.

Home in West Haven

Beach House steps from sand & Amazing Views

4.6 out of 5 average rating, 87 reviews

A serene view of the Great South Bay is captured, with sunlight reflecting off the water. The horizon is lined with soft clouds, and the foreground features a sandy beach bordered by lush greenery, providing a natural frame to the tranquil scene.

Home in East Patchogue

Beachfront / Seaside Home with spectacular view

4.93 out of 5 average rating, 40 reviews

An exterior view of the designer beach house is captured, showcasing its contemporary blue siding and multiple windows. A rooftop deck is visible, providing potential outdoor space. A grassy area is bordered by a white privacy fence, while neighboring structures can be seen in the background.

Home in Milford

Bohemian Beach Oasis- Private Beach