Beachfront holiday rental in Southold

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 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, 57 reviews

Best View + Putting Green + Private Beach

Perched high atop the Shinnecock Hills, our home boasts panoramic bay and ocean views unlike any other in the Hamptons! Located just 5 minutes from Shinnecock Hills Golf Club + your own private putting green, our property will create an awesome guest experience for the upcoming 2026 US Open! Tranquil, sanctuary like setting with manicured landscaping, mature privacy trees, waterfalls, like your own arboretum! Private beach, local favorite restaurants and hang outs are within walking distance!

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.

4.98 out of 5 average rating, 225 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

4.95 out of 5 average rating, 57 reviews

A weathered wooden sign is attached to a large tree, directing visitors towards the beach. The sign is marked with the words 'TO THE BEACH' and is surrounded by a grassy area with additional trees in the background, offering a sense of calm and connection to nature.

Home in North Fork

The North Star: Greenport Waterview Beach Getaway

Welcome to our charming home in Greenport, NY. Right across the street from the private community beach! We are neighbors to the most famous wineries on the North Fork. 3 bedrooms, 2 baths, & a den that has a pull-out queen sleeper sofa. Private beach. Outdoor shower. Comes fully equipped with towels & linens. 2 miles from the town of Greenport. Perfect house for families/groups. DOG(s) FRIENDLY (w/ a pet fee) with fenced front yard & deck- sorry no cats! Looking for adults aged 30 or over.

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).

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.

4.98 out of 5 average rating, 167 reviews

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.

4.9 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

A coastal cottage on the water surrounded by vineyards and farm stands on the North Fork. Unwind in the backyard with a private view of the Goldsmith's Inlet where you can watch the sunrise, bird watch, and admire our local swans. A quick 5-minute walk to the Long Island Sound where you can sunbathe, swim, kayak, and watch the beautiful sunset. Conveniently located near Greenport, Orient, and Southold. *IMPORTANT* Kayaks and grill are only available from May 1st to October 31st.

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,

5 out of 5 average rating, 19 reviews

The beachfront home features a wrap-around balcony and large windows that provide views of the shore. The exterior is surrounded by a stone wall and sandy beach, with a staircase leading down to the water from the deck.

Home in North Fork

Kayaks ~ Bikes ~ Boards ~ 6mins> Greenport ~ 55"TV

★ "Beautiful hidden home on the water… enjoy the North Fork summer in style." Private beachfront property with 2 homes & views of Gardiner’s bay. ☞ Bikes + kayaks + paddle boards ☞ Wrap around balcony w/ seating ☞ Fully equipped + stocked kitchen ☞ Deck w/ lounging + water views ☞ Dedicated workspace + printer ☞ Master w/ king + bathroom ☞ 55” Smart TV + Xbox ☞ Indoor gas fireplace 6 mins → DT Greenport (cafes, dining, shopping) 13 mins → Orient Beach State Park ⛱

Popular amenities for Southold beachfront rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Pet-friendly beachfront home rentals

Superhost

A cottage is nestled among a lush garden with blooming flowers and manicured grass. The exterior features a combination of green siding and gray shingles. Pathways made of stones lead to the entrance, embracing a serene and inviting environment.

4.75 out of 5 average rating, 24 reviews

Southampton cozy cottage by the beach.

The interior of a safari tent is shown, featuring a queen bed dressed in white linens. A nightstand and dresser are located beside the bed. A covered porch area with seating is visible through large, screened openings, showcasing views of nature and the water beyond.

Tent in The Hamptons

4.79 out of 5 average rating, 29 reviews

Safari Tent Glamping,S15-CedarPt, East Hampton, NY

Aerial view of a waterfront community features several quaint houses along a serene creek. Lush greenery surrounds the area, with water gently reflecting the sky. A dock extends into the water, offering access for outdoor activities.

5 out of 5 average rating, 4 reviews

Roy's Cottage

The exterior of a contemporary home is shown, featuring a mix of wood siding and large windows. A spacious deck is visible, accompanied by green grass and a swing set in the foreground. Nearby, additional residential structures are partially seen in the background.

Home in South End

Southold Beach House

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.

4.87 out of 5 average rating, 91 reviews

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

A serene coastal view captures a vibrant sunset, where the sun dips below the horizon, casting warm hues across the sky. Gentle waves lap against dark rocks, creating a tranquil atmosphere along the shore. The scene evokes a sense of calm and natural beauty.

4.92 out of 5 average rating, 63 reviews

Cottage in Calverton

A two-story oceanfront home features a modern design with large glass windows and a sloped roof. Multiple balconies provide access to outdoor views, while a white fence encloses the property. Surrounding dunes with tall grass add to the tranquil coastal setting.

5 out of 5 average rating, 8 reviews

Oceanfront Home, Spectacular Views from Each Room.

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.

4.95 out of 5 average rating, 75 reviews

Beach Cottage 3 | New Suffolk | Northfork

Beachfront home rentals with a pool

An outdoor private pool is surrounded by lush greenery and colorful flowers, providing a serene backdrop. Wooden lounge chairs are positioned around the pool area, creating inviting spaces for relaxation. The clear blue water of the pool contrasts beautifully with the natural tones of the surrounding landscape.

Bayside Sensation in Southampton

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

Superhost

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

4.8 out of 5 average rating, 25 reviews

Waterfront Elevated Bungalow - Spectacular Views

A spacious heated in-ground pool is surrounded by a stone patio and vibrant landscaping. Lounge chairs are arranged along the poolside, accompanied by a large umbrella for shade. Lush greenery and blooming flowers frame the area, creating a serene outdoor retreat.

4.97 out of 5 average rating, 72 reviews

4 BR Hamptons Oasis w/ Pool,Jacuzzi & Beach Access

A charming guest house is framed by a large tree and lush green lawn. The porch features white railings and potted plants, inviting relaxation. A gravel pathway leads to the entrance, while the backdrop showcases a horse paddock and carefully maintained greenery.

5 out of 5 average rating, 16 reviews

Bayfield Farms Country Estate Guest House

Apartment in Greenport

New place to stay

Waterfront Renovated Duplex

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!

Guesthouse in The Hamptons

A row of charming cottages is positioned along a neatly manicured lawn, with lush greenery surrounding them. The cottages feature wooden decks that offer outdoor seating areas, while trees stand tall in the background, contributing to a serene environment.

5 out of 5 average rating, 23 reviews

One Bedroom Hamptons Waterfront Cottage

Private beachfront home rentals

4.92 out of 5 average rating, 25 reviews

Beach cottage on Noyac Bay

The exterior of the cottage is shown, featuring a blue shingle facade and inviting double doors. A gravel pathway leads to a spacious patio with two chairs, surrounded by greenery, under a vibrant sunset sky.

5 out of 5 average rating, 9 reviews

Beach cottage bungalow

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, 80 reviews

Hamptons Waterfront Escape/ Hot Tub/ Resort Style

A wooden deck features comfortable seating with white cushions, positioned around a small table set with tea and pastries. Lush green grass surrounds the area, dotted with tall trees, while a clear view of the harbor can be seen in the background.

4.82 out of 5 average rating, 38 reviews

Historic East Hampton Home - Private Beach Access

Superhost

Two white Adirondack chairs are positioned near a fire pit, offering a scenic view of the calm water and a partially cloudy sky at sunset. Pebbles and grassy areas surround the seating, enhancing the serene beach atmosphere.

Apartment in South End

4.79 out of 5 average rating, 67 reviews

Incredible 2 Bedroom Waterfront Cottage!

4.92 out of 5 average rating, 52 reviews

Home in Shirley

Waterfront Designer Retreat | Fire Pit & Sunsets

A bright living room features a white sofa and a lounge chair, creating a comfortable seating area. Natural light fills the space through large windows dressed with sheer curtains, which overlook a serene outdoor scene. A stylish coffee table sits centrally on a soft area rug.

Cottage in South End

4.74 out of 5 average rating, 197 reviews

Cozy&Chic Beach Cottage (wineries, remote working)

A spacious deck featuring a seating area with comfortable lounge chairs and a dining table. Large umbrellas provide shade while offering panoramic views of the water below. The clear blue sky aligns with the serene bay, creating a peaceful outdoor retreat.