Waterfront vacation rentals in Shirley

4.94 out of 5 average rating, 178 reviews

An aerial view captures the serene neighborhood, showcasing small homes interspersed with trees and greenery. The bay can be seen in the distance, along with the nearby beach access. The well-maintained grounds of the property highlight a clean, welcoming environment.

Home in Shirley

Waterview Beach House: 3 Kings + Putting Green

Unwind at this 3-story waterview beach home in Shirley, NY. Bellport Bay is right across the street with easy beach access. 0.4 mi to Shirley Beach 1.8 mi to Smith Point Beach — perfect for ocean days or Fire Island trips. Featuring: • 3 king beds + 1 full + 3 sofa beds • 70” living room TV + 3x 50” bedroom TVs • Fully equipped kitchen • BBQ grill, fire pit & putting green on premium turf • 6 beach chairs + 2 umbrellas included • High-speed WiFi & keyless entry Your Long Island beach escape!

4.98 out of 5 average rating, 226 reviews

An expansive deck offers a view of the Great South Bay, with a mix of comfortable seating options, including lounge chairs and a sectional sofa. The area is complemented by manicured green grass and a wooden railing, providing a serene backdrop for outdoor relaxation.

Home in Shirley

Luxurious Waterfront Beach House On The Bay

Relax and enjoy your time at this beautiful east end waterfront getaway. This house is located right on the relaxing and exclusive Great South Bay with private beach... The experience will bring you the feel of tranquility everyone desires with vacationing out east. While offering all the enjoyments the island has at your fingertips. Centrally located to all island destinations. 90 minutes from Manhattan - 15 minutes to West Hampton - 15 minutes to Fire Island Ferrys. Visit top winery’s WiFi

4.84 out of 5 average rating, 135 reviews

Hamptons Oceanfront Oasis

Escape the hustle & bustle of city life and unwind at this stunning home in the Hamptons. The oceanfront oasis is the perfect way to wake up to ocean views, beaches and nearby restaurants. Relax on our spacious deck - perfect for morning coffees & sunset cocktails. It is just a short drive to the train station & only 15 minutes from the airport for quick getaways. For your safety, the home is equipped with Ring cameras and one-use key codes. Book now and experience the ultimate Hamptons escape!

4.97 out of 5 average rating, 623 reviews

An expansive patio extends towards the shimmering waters of Long Island Sound, featuring lounge chairs and a dining table with an umbrella. Decorative planters and lanterns are arranged along the patio edge, complementing the serene waterfront view.

Apartment in Milford

Water front studio apartment with fireplace.

This is a beautifully appointed studio apartment located off the patio level of a water front home. Guests enjoy a large private patio over looking gorgeous sweeping views of Long Island Sound. A private entrance and off street parking. The amazing views and amenities make this space the perfect romantic getaway! Close to I95 and Metro North railroad. Ten minutes to great dining in downtown Milford. A true waterfront oasis! Come and experience this beautiful retreat! You won't be disappointed!

4.83 out of 5 average rating, 195 reviews

A spacious living area features large glass windows that frame a stunning sunset over the water. The open design enhances natural light, illuminating the room's elegant furnishings and wooden accents. A dining table is positioned near the windows, inviting relaxed meals with a view.

Cabin in Shirley

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.

4.97 out of 5 average rating, 258 reviews

An aerial view showcases a coastal neighborhood with homes situated along a sandy beach. Vibrant blue waters and marshlands surround the area, emphasizing its seaside location. The arrow points to the property's location within the community, illustrating proximity to the beach.

Home in Milford

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!

4.81 out of 5 average rating, 390 reviews

A charming red cottage is set among lush greenery, showcasing a manicured lawn leading to the porch. The house features a rustic stone chimney and a welcoming front porch adorned with white railings. Nearby, a small structure complements the main home with a rounded window.

Home in Port Jefferson

The Hilltop Harborview

Guests will immediately walk past spacious hot tub into a comfortable sunroom where you’ll watch the most colorful, water view sunsets Long Island has to offer! This one of a kind offers a sprawling layout that has 3 queen size bedrooms and 1 king . We can also provide an air mattress for an additional guest. There is a kitchen equipped with stove, oven, dishwasher and washer and dryer! This beautiful walking Village has so much to offer! We do allow dogs with prior notice with a $65/dog.

4.94 out of 5 average rating, 133 reviews

A calm waterfront scene features a vibrant sailboat gliding across the bay, surrounded by green marshland. A wooden dock leads into the water, with several colorful chairs positioned for relaxation. Soft hills and houses line the distant shore under a gentle mist.

Home in Mastic Beach

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.

4.98 out of 5 average rating, 168 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.

4.89 out of 5 average rating, 165 reviews

An outdoor deck is seen featuring a spacious octagonal hot tub. It overlooks a calm canal bordered by green grass and trees. Nearby boats are docked, and the tranquil water reflects the clear sky, creating a peaceful atmosphere.

Home in Oakdale

Waterfront Round House View

A unique little beach house on the south shore of long island with the most beautiful view. The house is located on a canal. Dock is available! **We have Paddle Boards, Surf Boards and 3- 2 person Kayaks onsite for you to use during your stay** You can get to the Great South Bay by paddling to the mouth of the canal. And you can get to Fire Island by hiring a Water Taxi to pick you up! The octagon house was built in the 1970s. It's recently been refreshed with all new beds & linens.

4.93 out of 5 average rating, 145 reviews

A patio is shown with a wooden table and a dark wicker chair overlooking a scenic view. A clear sky with scattered clouds is visible in the background, along with open fields and distant structures. Utility poles line the road, adding context to the setting.

Home in Patchogue

Joyful Beach House, viewing The Great South Bay

Amazing Great South Bay view with access to Shorefront and Rider Parks. This Ranch has an unobstructed view of the Shorefront Band Shell. Watch concerts and sunsets from the comfort of your patio. Walk down to the Patchogue Beach Club and enjoy the pool and beach. This open-concept home has 2 bedrooms, one bath, a remodeled bathroom, and a kitchen. The kitchen has stainless steel appliances, a farm sink, and a butcher block countertop with natural lighting that will brighten the home.

4.95 out of 5 average rating, 170 reviews

An inviting waterfront deck is displayed, featuring two lounge chairs with striped fabric and a small table. A fire pit sits nearby, surrounded by a clear view of the bay, where sailboats are gently anchored. Lush greenery lines the horizon, enhancing the serene atmosphere.

Home in Centerport

The Harbor House: Beachfront Home 1 hour from NYC

FEATURED #1 on Refinery29's "11 Best Beach Houses Near NYC" Welcome to Long Island’s iconic Gold Coast! Wake up to sweeping waterfront views and, if you’re lucky, catch a glimpse of our local bald eagle family soaring overhead! Explore nearby gems like the Vanderbilt Mansion & Planetarium, Caumsett State Historic Park Preserve, Del Vino Vineyards, and the lively Paramount Theatre. Stroll through Downtown Huntington or Northport Village for boutique shopping, great restaurants.

Popular amenities for Shirley waterfront rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Waterfront apartment rentals

4.88 out of 5 average rating, 8 reviews

Apartment in West Islip

Lakefront GetawaY & Romantic NightS + BeacheS NeaR

Apartment in Rockaway Beach

4.81 out of 5 average rating, 301 reviews

Beachfront apartment with ocean view and huge deck

4.92 out of 5 average rating, 25 reviews

A peaceful beach scene captured at night reveals a sandy shoreline reflecting moonlight. Houses line the beach, their warm lights creating a welcoming glow. Calm waters extend to the horizon, while scattered clouds drift in a starry sky, enhancing the serene coastal atmosphere.

Apartment in Milford

Spring is here & the beach is near! BOOK NOW!

Apartment in The Hamptons

4.94 out of 5 average rating, 88 reviews

Hamptons Waterfront Suite | Private Hot Tub

4.83 out of 5 average rating, 228 reviews

A wooden dock extends into the water, lined with boats gently bobbing on the surface. Lush green hills rise in the background, while a clear blue sky with scattered clouds frames the scene. People are gathered along the dock, enjoying the views.

Apartment in Northport

Harbor Studio - Across from historic Northport doc

5 out of 5 average rating, 11 reviews

Apartment in North Fork

Greenport Condo with Stunning Views & Beach Access

5 out of 5 average rating, 69 reviews

An aerial view captures the peaceful Great South Bay area, showcasing a residential neighborhood with various boats and docks along the canal. A mix of homes and buildings line the streets, surrounded by lush greenery, contributing to the serene coastal atmosphere.

Apartment in Bay Shore

Turtle Dove Cozy Gem on the Bay

4.96 out of 5 average rating, 76 reviews

A two-story beach apartment is shown with a light blue exterior and white railings. A staircase leads up to a front deck, surrounded by colorful flower beds. Large windows on the upper level provide ample natural light, while an inviting entrance is seen below.

Apartment in Milford

Steps to the Beach. Lovely 2-Bedroom apt

Waterfront house rentals

4.96 out of 5 average rating, 28 reviews

A stunning view of Hashamomuck Inlet is captured during sunset, with soft clouds reflecting warm hues on the water. A wooden deck leads to the waterfront, framed by grasses and small rocks, enhancing the sense of tranquility in this natural setting.

Home in Southold

North Fork Waterfront Escape · Sunset Views

4.83 out of 5 average rating, 116 reviews

A spacious outdoor deck area is visible, leading to a sandy beach. The house features large windows on the upper level, allowing natural light to fill the interior. Surrounding buildings include a mix of colors and styles, contributing to the residential atmosphere.

Home in Milford

Beachfront house on Long Island Sound

A modern two-story house is positioned amid landscaped grounds, featuring mature trees and a lush green lawn. The facade showcases expansive windows, which reflect the colors of the sunset sky. A smooth driveway leads up to the entrance, providing a welcoming approach.

4.96 out of 5 average rating, 69 reviews

Best View + Putting Green + Private Beach

5 out of 5 average rating, 23 reviews

The kitchen features modern appliances set against white cabinetry, complemented by black bar stools. An outdoor gathering area showcases a circular fire pit surrounded by black Adirondack chairs, with waterfront views in the background. A cozy bedroom displays a large bed with decorative pillows and natural light filtering through the window.

Home in Stratford

Charming Riverview Home • Firepit • Train & I-95

4.87 out of 5 average rating, 38 reviews

A serene waterfront view captures a calm river lined with greenery. A boat is docked at a wooden platform, with additional boats visible in the distance. Vibrant yellow flowers frame the foreground, contrasting with the rich greens of the landscape under a clear blue sky.

Home in Oakdale

Riverfront Retreat in Oakdale

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, 251 reviews

Private beach, fully updated house, on 2 acres.

5 out of 5 average rating, 5 reviews

Home in Shirley

Shirley Bayfront Getaway

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, 105 reviews

Breezy Waterfront Home With private Dock

Waterfront condo rentals

The kitchen features modern appliances, including a stove and refrigerator, complemented by open shelving displaying dishware. A dining area with a spacious table is visible, along with large glass doors that provide a view of the waterfront. Natural light enhances the warm atmosphere.

5 out of 5 average rating, 7 reviews

Water front, sunsets, sail boats, Wi-fi, birds

A living area features shiplap walls and ample natural light from large windows. A dark sectional sofa is positioned next to a glass coffee table with a small plant. An open kitchen area is visible, along with access to a screened porch through sliding doors.

4.86 out of 5 average rating, 130 reviews

Beautiful condo on Long Islands Northfork

A light-filled living area features a cozy neutral sofa, accompanied by a matching armchair. A decorative coffee table sits in the center, and a Smart TV is mounted on the wall. Sliders lead to a private waterfront deck with seating, enhancing the space's openness.

4.84 out of 5 average rating, 160 reviews

Waterfront Escape | Private Beach, Pool & Views

4.92 out of 5 average rating, 38 reviews

A spacious living area is highlighted by exposed wooden beams and brick walls. Natural light streams through two large windows. Comfortable seating is provided by a leather couch facing a low coffee table. A wooden dining table with chairs sits in the corner, adding functionality.

Condo in Long Beach

City style apartment, Beach Passes Included

The living area features a spacious dark gray couch, a light wooden coffee table, and a white dining table with woven chairs. Natural light filters through the window with plantation shutters, while decorative elements like a round mirror and wall art create a welcoming ambiance.

4.9 out of 5 average rating, 178 reviews

Beautiful Waterview Condo on the North Fork of LI

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.

4.88 out of 5 average rating, 160 reviews

Waterfront Escape | Private Beach, Pool & Views

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.

4.91 out of 5 average rating, 149 reviews

Beachside Waterview 2Br Condo w/ Pool in Greenport

The living area features a comfortable seating arrangement with a dark couch and light-colored accent chairs. A dining table sits nearby, accompanied by additional seating. Large windows offer natural light, with greenery visible outside. A flat-screen TV and decorative mirror add to the space.