Waterfront holiday rentals in Shirley

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

4.97 out of 5 average rating, 101 reviews

The kitchen features modern cabinetry with a contrasting dark granite island. Three cushioned stools are positioned at the island. Natural light enters through a window above the sink, illuminating new stainless steel appliances and a sleek backsplash. A door leads to the outdoor area.

Home in Black Rock

Cape on the Water

Welcome to our Cape on the Water! This unique property is located on beautiful Ash Creek, an inlet off Long Island Sound offering views of tidal wetlands, including tons of fish, bird, kayakers, paddle boarders, small sail boats etc. The house is a newly renovated Cape Cod with open floor concepts, updated Kitchen and bath rooms. Refinished oak hardwood floors through out the entire house. Brand new large deck. The house has a very cozy feel and has been also updated with brand new HVAC system.

A bright living area features large windows that offer views of the nearby pond. Comfortable seating includes a white sofa, patterned chairs, and a coffee table, all arranged on a natural fiber rug. Light from the windows enhances the serene atmosphere.

4.87 out of 5 average rating, 117 reviews

Sag Harbor, Designer w large Pool (3 bed/2.5 bath)

Relax with friends / family at this home in a magical setting overlooking Lily pond Completely private but 5 mins to Sag Harbor downtown / restaurants / Havens beach, and 10 mins to Bridgehampton. Location, location! And Views! - 3 Beds and 2.5 baths + pool house - Pool house with twin sofa bed + full bath - 50ft heated Gunite pool (125/d extra to heat) - Outdoor deck overlooking pond - Amazing views! - Fire pit with Adirondack chairs Unique house to unwind while being close to the action

4.88 out of 5 average rating, 118 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, 613 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!

4.93 out of 5 average rating, 169 reviews

A serene waterfront view is presented, showcasing calm waters reflecting a soft pink sky. Lush green grasses frame the foreground, while a tree line marks the horizon, creating a tranquil landscape. A few ducks can be seen gently floating on the water.

Loft in Milford

Lovely water front lower-level loft, free parking

This unique centrally located water front loft is located on the second Gulf Pond 1.5 miles from historic Milford center buzzing with water front restaurants and downtown shopping. This one bedroom, one bath, has a private entrance and free off street parking. Outdoor patio & grill with kitchenette, enjoy a waterfront view throughout the 400 sq ft space. Close to I-95, the Merrit Parkway, and Milford train station. Explore 17 miles of beaches in this New England town by bike, kayak, or foot.

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.

4.93 out of 5 average rating, 139 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, 136 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

4.97 out of 5 average rating, 196 reviews

A modern, two-story structure showcases large windows framed by climbing greenery. A stone pathway leads to a glass-paneled door, with potted flowers positioned along the entrance. The surrounding area is filled with trees, creating a serene atmosphere.

Cottage in Weston

The River Loft

Escape to The River Loft, a private riverfront retreat in Weston, CT. Built in 2015 by a visionary local architect, The River Loft open-air design seamlessly integrates the outdoors with the interior space. As you step inside this 750 sf small home, you'll be instantly captivated by the layout that makes it feel spacious. Sitting on over 2 acres of forested land with private river access. Book now for an unforgettable experience. For more images & videos visit insta @the.riverloft

4.92 out of 5 average rating, 154 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.

4.84 out of 5 average rating, 220 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

Across the street from historic Northport dock and the beautiful town park, this downtown studio is walking distance to everything. Drive or boat in to town and have a lovely convenient place to stay close to everything. Dining, shopping, the park, and the Famous Engleman theater. The studio has a private entrance, full kitchen, and bath with shower and tub. Enjoy a night, weekend, or whole week in historic Northport Village.

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, 7 reviews

Apartment in West Islip

Lakefront GetawaY & Romantic NightS + BeacheS NeaR

5 out of 5 average rating, 5 reviews

Apartment in Cos Cob

2-Mini Bedrooms.

5 out of 5 average rating, 79 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 The Hamptons

A serene waterfront view showcases a private deck adorned with lush greenery and vibrant flowers. A saltwater hot tub and lounge area invite relaxation, while the expansive water stretches into the distance. Comfortable seating arrangements enhance the tranquil outdoor environment.

4.94 out of 5 average rating, 81 reviews

Hamptons Waterfront Escape/ Hot Tub/ Resort Style

4.98 out of 5 average rating, 45 reviews

A well-lit sleeping area features a modern bed with crisp linens and patterned blankets. Side tables are positioned beside the bed, with lamps providing soft lighting. Natural wood flooring enhances the cozy atmosphere, while hooks on the wall offer convenient storage.

Apartment in Fire Island

Studio for 2 in Cherry Grove, Fire Island

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.

4.84 out of 5 average rating, 103 reviews

Water View SONO 2 Bedroom Walk to Metro & Dining

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

Waterfront house rentals

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.

4.83 out of 5 average rating, 112 reviews

Beachfront house on Long Island Sound

A landscaped yard features a lush green lawn framed by mature trees and bushes. The expansive bay and ocean views are visible in the background. A colorful sunset paints the sky, creating a serene and tranquil setting.

4.98 out of 5 average rating, 60 reviews

Best View + Putting Green + Private Beach

5 out of 5 average rating, 47 reviews

An aerial view captures the heated saltwater pool surrounded by a spacious patio. Lounge chairs and shaded seating areas are arranged near the pool, with outdoor furniture positioned for relaxation. Lush greenery and a landscaped garden frame the space, providing a serene environment.

Home in Yaphank

Long Island Getaway w/ Heated Pool & Lake

4.95 out of 5 average rating, 127 reviews

Oceanfront Beach House w/ Private Hot Tub

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

A renovated kitchen is presented, featuring a central island with bar stools and modern appliances. Soft green backsplash tiles add a refreshing touch, while natural light pours in through the windows, illuminating the clean lines and open layout of the space.

4.94 out of 5 average rating, 33 reviews

Hamptons Home, 3bed/2bath Near Beach & Restaurants

The exterior of a two-story beach house is displayed, featuring a light-colored facade with a welcoming front porch and a gravel driveway. Inside, bright, open living spaces include a modern kitchen with sleek black appliances, a comfortable living area with a sofa, and a serene bedroom filled with natural light.

4.98 out of 5 average rating, 85 reviews

Luxe Beach House / 3 Bd-King / Chef Kitchen /4 TV

A vibrant sunset fills the sky with hues of pink, orange, and purple, reflecting on the tranquil water. Silhouettes of two birdhouses are visible on posts in the foreground, framed by lush vegetation along the shore.

4.98 out of 5 average rating, 138 reviews

3 Bedroom Beach House with Hot Tub!

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.

4.86 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

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

4.51 out of 5 average rating, 78 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, 176 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.