Waterfront vacation rentals in Northwest Harbor

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, 154 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

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.

A spacious living area features a large sectional sofa adorned with various cushions, set against a backdrop of windows that provide ample natural light. A round coffee table with a vase of flowers sits in the center, creating a welcoming space for relaxation and conversation.

4.83 out of 5 average rating, 102 reviews

Montauk Private Beach Bungalow

Beautiful secluded cottage tucked away at the end of cul-de-sac and surrounded by a nature preserve. Montauk’s finest waterfront dining and bars are less than a mile. The house has a large living room with a fireplace, king bed in one and a full bed with a twin bunk in the other, a full bath, and an eat-in kitchen with dining for 6. There is a large very private patio with a grill, dining table and lounge area. The private beach is stunning and a 3 minute walk from the house. Pets are welcome.

4.88 out of 5 average rating, 104 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!

Two wooden Adirondack chairs are positioned on a spacious sun deck, overlooking expansive views of lush greenery and the waterfront. The bright blue sky complements the serene atmosphere, creating an inviting space for relaxation and enjoyment of the natural surroundings.

5 out of 5 average rating, 240 reviews

Montauk Waterfront Condo w/ Sunset Views

Modern 1 Bedroom Condo in gated community (Rough Riders) with sunset views from beautiful deck. The community has multiple tennis courts, pool, jacuzzi, and sauna (pool / sauna / jacuzzi only open Late May - early October). The property is great for walks along the boardwalk and many guests enjoy swimming off the pier. The unit is less than a 5 minute car / Uber ride to town and a short 5-10 minute walk to Navy Beach and Duryea's. Strong wifi in unit, Smart TV ( Netflix, etc, - no cable)

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

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

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.

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.

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,

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).

4.93 out of 5 average rating, 150 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.

4.9 out of 5 average rating, 227 reviews

A clear blue saltwater pool is surrounded by a landscaped yard featuring green grass and shrubs. Several lounge chairs are positioned nearby under light blue umbrellas, providing shade. A two-story house is visible in the background, framed by tall trees.

Home in North Fork

Greenport Beach house Mini Resort Spa & Catering

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).

Popular amenities for Northwest Harbor waterfront rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Waterfront apartment rentals

A light-filled living area features a comfortable sofa and glass coffee table. A dining table for four is set beside a large artwork depicting calm ocean hues. Sliding doors provide access to the balcony, enhancing the open and airy feel of the space.

5 out of 5 average rating, 8 reviews

Updated 4 Bed, 1 Bedroom Waterfront Condo

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, 80 reviews

Hamptons Waterfront Escape/ Hot Tub/ Resort Style

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

A bright and airy bedroom features a spacious bed with neutral bedding and decorative pillows. A large window with a sloped ceiling allows natural light to fill the space. A minimalist bookshelf and a cozy reading area with a lamp provide a welcoming touch.

4.94 out of 5 average rating, 16 reviews

Bayside Boho Retreat

An updated modern bathroom features white subway tiles and a glass shower enclosure. A marble vanity with brushed gold fixtures complements the sleek design. Fresh towels are neatly arranged for guest convenience, with a decorative mirror reflecting a light blue accent wall.

4.76 out of 5 average rating, 21 reviews

Oceanside Studio on Old Montauk Highway - Incredib

A clear view of the ocean is captured from the private deck, with sunlight sparkling on the water's surface. The horizon shows a calm sea under a bright sky, while a stretch of land and road can be seen in the foreground.

5 out of 5 average rating, 4 reviews

Oceanfront Condo in Montauk

5 out of 5 average rating, 3 reviews

Apartment in North Fork

Greenport Condo with Stunning Views & Beach Access

4.79 out of 5 average rating, 344 reviews

A spacious living area showcases a light grey sectional sofa and a matching loveseat arranged around a wooden coffee table. A striped area rug adds a pop of color to the dark flooring. Shelves line the walls, and large windows allow natural light to fill the room.

Apartment in North Fork

Amazing Greenport Village Apartment in CENTER!

Waterfront house rentals

5 out of 5 average rating, 44 reviews

A spacious backyard is featured, with a circular stone fire pit surrounded by several colorful Adirondack chairs. Lush green grass extends towards a charming white house in the background, bordered by trees under a clear blue sky.

Home in South End

Private Waterfront Access + Hot Tub + Scenic Yard

4.89 out of 5 average rating, 28 reviews

A beachfront house with a wooden exterior is depicted, featuring multiple windows adorned with green planters. Soft sand covers the area in front, leading to the water, which reflects the clear blue sky. A small chair is visible on the sand, emphasizing the serene beach setting.

Home in North Fork

The Sandy Shack - Coastal Escape

4.95 out of 5 average rating, 44 reviews

A striking sunset is captured over Bellport Bay, with vibrant hues of orange and pink reflecting on the water. Silhouettes of grasses frame the foreground, while a small wooden structure is visible, complementing the serene coastal view.

Home in Shirley

Sunset Cottage - Waterfront Getaway

4.9 out of 5 average rating, 30 reviews

A serene backyard is depicted, featuring a soft green lawn bordered by flourishing plants and flowers. Stone pathways meander gently through the garden, leading towards a view of the water. Trees provide shade, enhancing the natural, peaceful setting.

Home in South End

Coastal Cottage on the Water

4.94 out of 5 average rating, 129 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!

A bright and airy outdoor space features a long pool bordered by lounge chairs and greenery. The white house stands in the background, with large windows reflecting the blue sky. An umbrella provides shade beside the pool, promoting relaxation.

5 out of 5 average rating, 46 reviews

Beautiful Southampton Home w/ Pool, Close to Beach

A bright, open-concept living space is featured, with large windows allowing natural light to fill the room. A wooden dining table accommodates several chairs, while a cozy seating area includes a sofa and a television. Surfboards are mounted decoratively on the wall.

5 out of 5 average rating, 79 reviews

Modern Beach House - Walk to Town & Beach

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

Waterfront condo rentals

A serene twilight scene features a calm waterfront with soft hues of orange and blue in the sky, reflecting over the still water. A winding boardwalk leads towards the horizon, illuminated by subtle lights. A pier stands in the distance, enhancing the tranquil ambiance.

5 out of 5 average rating, 5 reviews

Montauk Sunset at your fingertip!

A serene view from inside the co-op, showcasing a wooden deck with wicker chairs. The sandy beach and water are visible beyond the doors. Soft light filters through, indicating a tranquil atmosphere during sunset.

4.89 out of 5 average rating, 9 reviews

Montauk on Fort Pond Bay Summer Rental

An aerial view displays the condo complex adjacent to the waterfront, featuring a central pool surrounded by a landscaped patio. The blue ocean extends beyond the property, with boats visible in the distance under a clear sky, enhancing the serene coastal environment.

4.94 out of 5 average rating, 34 reviews

Sun N Sound Resort, Montauk, NY

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, 126 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, 156 reviews

2 BR Waterfront Autumn Escape in Wine Country

A spacious studio is shown, featuring a king-size bed with crisp white linens. Natural light floods the room through large sliding doors that open to a private balcony with views of the waterfront. A ceiling fan hangs above, and a sitting area with a green sofa is present.

4.9 out of 5 average rating, 10 reviews

Endless Summer Studio Condo w Balcony Bayview

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

A serene sunset illuminates the horizon over calm waters, with soft golden reflections stretching across the surface. The sky displays subtle gradients of orange and blue, creating a tranquil atmosphere as the day transitions to night.