Waterfront holiday rentals in Shirley

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.

4.89 out of 5 average rating, 158 reviews

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

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

4.88 out of 5 average rating, 113 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!

4.85 out of 5 average rating, 186 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.

4.86 out of 5 average rating, 125 reviews

A cozy studio features a comfortable bed adorned with floral bedding and soft pillows. A modern chair and side table complement the space. Light is provided by a bedside lamp, and the room is accented with turquoise curtains and a decorative mirror on the wall.

Apartment in Freeport

Eleg B&B Stu Apt steps frm Nautical Mile

-Pvt Studio -Special Occassion Decor -Bkfst: pcakes, waffles, Jimmy Dean -Mr. Cool A/C & Ht Pmp -Fireplace -Recliner/pull-out bed, -Bkfst bar, -Kitchenette -Kurig Mach -Elec Kettle -Mwave -Refrige -Toaster -Jet Blndr -Iron, Iron Bd, hangers, (Hallway closet) -Hair Dryer (Hlwy clst) -WiFi -Wht Noise Mach -PS4, Fire Stick, -Ergo Chr, Dsk, Mse, Mntr, Keybrd -50 Inch smt tv, -Bosch hot water, -5 min walk to Nautical Mile <40min train to Mhttn/JFK -Jones bch -Wstbry Mall -UBS Stadm -Eshr Pk

4.94 out of 5 average rating, 130 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, 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.

4.99 out of 5 average rating, 151 reviews

A spacious living area is equipped with a dark sofa, decorative cushions, and a light rug, complemented by natural light from windows. A wooden dining table with chairs is positioned near a sideboard, inviting relaxation and gatherings.

Cottage in Miller Place

Cozy Country Cottage #2

Relax and get away from it all at this newly renovated cottage in historic Miller Place. Enjoy your private fenced in backyard with your own deck, picnic table and BBQ. You can walk across the street to the historic Miller Place Pond or walk 2 blocks to the famous McNulty's Ice Cream Parlor. Take your beach gear 2 miles to Cedar Beach or go 4.5 miles to Port Jefferson for the best food and entertainment. So many options for dinning and entertainment. You are at the foot of wine country!

4.93 out of 5 average rating, 136 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.

4.97 out of 5 average rating, 131 reviews

A modern living room is highlighted by a set of white sofas with tufted detailing, accented by blue cushions. A light fixture with a circular design illuminates the space, while sheer curtains frame the windows. A coffee table and two armchairs complement the room’s layout.

Apartment in Freeport

Quiet Waterfront Entire Apartment

Nestled in South Freeport, this 1 Br apt brings it all within your reach. Whether you are hoping to relax/work while drinking coffee on the patio or living room over looking the water, this is a very quiet and relaxing place to be. 5 minutes from the famous Nautical Mile where you can enjoy different restaurants, boat rides and other activities, minutes away from Southern State and Meadowbrook Pkwy, 15 minutes away from Jones Beach. Near different universities. AC in bedroom as well

A serene scene features a well-kept pool surrounded by lounge chairs, reflecting the colors of the sunset. The main house and pool house are visible, each with large windows and inviting outdoor spaces. Lush greenery outlines the property, enhancing the tranquil setting.

4.85 out of 5 average rating, 113 reviews

Stunning Hamptons Waterfront Escape w/ Sunset View

Experience an unforgettable trip in the Hamptons at our waterfront haven! Savor the views from our spacious deck. Vaulted ceilings and large windows flood the space with natural light. Brand new Weber Grill (2025). We have completed renovations of 3 bathrooms, 2 kitchens, and the entire pool house over the last 18 months. Our home is <10 minutes drive to the beach, groceries, and restaurants! Note our pool and dock are closed and will open Memorial Day Weekend (late May 2026).

4.92 out of 5 average rating, 153 reviews

A bright living area features light-colored walls and wooden flooring. A comfortable sofa and a plush chair are arranged around a rustic coffee table. A ceiling fan hangs above, while a kitchen with a blue island is visible in the background, enhancing the space's openness.

Home in North Fork

Modern Farmhouse Steps to Beach & Love Lane

Our home is professionally designed and set on a spacious, manicured green parcel enclosed by a Cul-de-sac with complete privacy inside and out. The home is designed with all modern conveniences and is located less than a 5 minute walk to Love Lane (Mattituck's charming downtown), Veteran's Beach (one of the best beaches on the Northfork) and the Mattituck train station. It is a place to relax, unwind and enjoy all that North Fork has to offer.

Popular amenities for Shirley waterfront rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Waterfront apartment accommodation

4.86 out of 5 average rating, 44 reviews

A compact kitchenette features wooden cabinets and a granite countertop. A white refrigerator stands beside a microwave, while a sink is available. The backsplash showcases a mix of neutral tiles, and the floor is finished with light-toned planks, enhancing the space's open feel.

Apartment in Massapequa

Island beach NY Waterfront Apt.

4.99 out of 5 average rating, 155 reviews

The bedroom features a queen bed with a colorful marine-themed bedding set. Light blue walls complement the natural wood flooring. Two windows allow ample natural light, with blinds for privacy. Decorative elements include beach-themed art, a nightstand, and a dresser.

Apartment in Northport

Amazing one bdrm flat at the beach!

5 out of 5 average rating, 78 reviews

The exterior of a historic brick building displays vibrant red accents and festive decorations. American flags are hung on the facade, with a decorative wreath on the door. Showcasing a welcoming entrance, the space is complemented by a brick pathway leading to the door.

Apartment in Wall Street

Phoenix Engine #1

Apartment in The Hamptons

A cozy living area features wood-paneled walls and a neutral sofa positioned near a lamp and a chair. Natural light floods through the windows, illuminating a patterned rug on the hardwood floor. A television is mounted on the wall opposite the entrance.

4.92 out of 5 average rating, 12 reviews

Sugarloaf Annex

Apartment in South Norwalk

A comfortable living area features a black sofa and a light-colored couch with decorative pillows. A wooden coffee table sits at the center, surrounded by a small dining table and chairs. Soft lighting is provided by a stylish fixture, and natural light enters through the windows.

4.88 out of 5 average rating, 100 reviews

Water View SONO 2 Bedroom Walk to Metro & Dining

5 out of 5 average rating, 5 reviews

Apartment in North Fork

Greenport Condo with Stunning Views & Beach Access

5 out of 5 average rating, 67 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

4.94 out of 5 average rating, 53 reviews

A spacious room features warm hardwood floors and large windows allowing natural light. A king size bed is adorned with light bedding and soft pillows. A comfortable sofa can be seen in the background, alongside a wooden coffee table and plants, fostering a relaxed atmosphere.

Apartment in Stamford

Spacious. Water Views & Access. Steps to Beach.

Waterfront house rentals

4.94 out of 5 average rating, 31 reviews

An outdoor dining area is visible, featuring a dark wicker table surrounded by six matching chairs. Steps lead down to a serene waterfront, framed by lush trees displaying autumn colors. The calm water reflects the clear blue sky, creating a tranquil setting.

Home in Ridge

Lake Panamoka Bliss 3BR High End Home, Lakeside

4.9 out of 5 average rating, 39 reviews

The exterior of a modern cottage is presented with a black wood facade and multiple windows. A front porch is seen, partially enclosed with slatted wood. Lush green grass and shrubbery frame the entrance, creating a welcoming approach to the home.

Home in North Fork

Waterfront NoFo Cottage w/ public beach access

5 out of 5 average rating, 15 reviews

The living room features a spacious sectional sofa with decorative cushions, arranged around a round area rug. Natural light filters in through multiple windows, revealing a calming color palette of gray and blue. A coastal-themed art piece is displayed on the wall, adding a touch of character.

Home in Patchogue

Coastal living

4.95 out of 5 average rating, 262 reviews

A spacious outdoor pool is surrounded by natural greenery, featuring a stone patio and a diving board. A covered lounge area with large windows overlooks the pool, providing a serene setting for relaxation and leisure.

Home in Stamford

Midcentury Modern ZenHouse Sculptor Studio

4.91 out of 5 average rating, 173 reviews

The kitchen is designed with white cabinetry and stainless-steel appliances, including a refrigerator and gas stove. A large island with seating is positioned across from the sink, illuminated by natural light from nearby windows. Hardwood flooring adds warmth to the space.

Home in Bay Shore

The Harbor House

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

A bright and airy living space features a cozy beige sofa facing large windows with water views. A staircase leads to the upper level, and natural light illuminates the open layout. Light-colored furniture and decorative accents create a relaxing coastal ambiance.

4.97 out of 5 average rating, 32 reviews

Magnificent Bayfront Retreat

A bright living room features large windows that showcase water views. Comfortable white sofas are arranged around a wooden coffee table, while a dining area is visible in the background. A ceiling fan and a wall-mounted TV add to the room's functionality.

4.91 out of 5 average rating, 46 reviews

Wake up to Stunning Views at a Serene Waterfront Haven

Waterfront condo accommodation

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.

4.83 out of 5 average rating, 6 reviews

Beautiful 2 Bedroom 2 Bathroom Pool-Side Condo

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.

4.88 out of 5 average rating, 103 reviews

Waterfront Condo C-204 at The Cliffside Resort

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.

4.87 out of 5 average rating, 127 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.

4.85 out of 5 average rating, 159 reviews

2 BR Waterfront Autumn Escape in Wine Country

A tranquil waterfront scene is captured at sunset, with the sky painted in shades of pink and purple. The calm water reflects the vibrant colors, creating a mirrored effect. A dock can be seen in the foreground, adding to the serene atmosphere of the setting.

Condo in Freeport

4.55 out of 5 average rating, 77 reviews

Waterfront Zen - Private 2 Bedroom

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, 172 reviews

Beautiful Waterview Condo on the North Fork of LI

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.