Beachfront vacation rentals in Sag Harbor

4.88 out of 5 average rating, 160 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

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

Waterfront apartment in Flanders, a Southampton Hamlet – perfect for a couple’s retreat. Resort Style: large saltwater hot tub yr round, private dock with 2-person kayak, fire pit, lounge chairs, and beach towels. Features include self-check-in, private entrance, porch, central air, 55" smart TV, electric fireplace, and outdoor shower. Take in the waterfront beautiful sunrise and sunset views. Just 19 minutes to Southampton Village for restaurants and shopping. Adults only. No pets or children.

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, 250 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.

4.79 out of 5 average rating, 68 reviews

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

Incredible 2 Bedroom Waterfront Cottage!

An amazing & unique experience on the North Fork of Long Island. Sitting on a bluff 15’ above our private beach, this 3 season multi-family property boasts panoramic views of the LI Sound. Amazing sunset/sunrise views, fishing, beach combing, swimming, wineries, restaurants, shopping. Huge 2nd story deck for evening cocktails. Full kitchen, BBQ, loads of amenities. Updated inside & out. Private beach shared only with other guests of the property Please note there is some noise from passing cars

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, 73 reviews

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

Your dream Hamptons vacation! Located on the border of Southampton and Hampton Bays, this stunning home is nestled at the end of a private cul de sac, just steps away from the gorgeous Peconic Bay Beach. • In-ground Heated Pool w/lounge chairs • Outdoor Hot Tub • Outdoor Shower • 3-Burner Weber Grill • 1 Acre Yard fully fenced in that is child-friendly • Bay Beach Access • Minutes from the Ocean beach Longer stays (30+ nights) available by request. Please message for custom pricing.

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.

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

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,

The image captures a serene sunset over the Long Island Sound, with warm, golden light reflecting on the water. Silhouettes of trees and rocky shoreline frame the scene, which features a blend of colorful clouds in the sky, creating a calming and peaceful atmosphere.

4.95 out of 5 average rating, 63 reviews

North Fork Paradise

Welcome to your North Fork escape! Newly re-built, secluded beachfront home overlooking the Long Island Sound. Wood floors, classic North Fork styling, washer/dryer, great kitchen and stellar internet. The home has direct beach access via private staircase on the property and is minutes from historic Greenport. Spend your days in idyllic surroundings as you relax in the backyard or read in the vintage living room; spend your evenings using the BBQ and sitting around the firepit!

Place to stay in The Hamptons

4.97 out of 5 average rating, 147 reviews

Walk-To-The-Beach House In The Dunes

(Weekly in season! Please inquire before booking!) This south-of-the highway artist residence is just three minutes by foot to the ocean. Up to 4 bedrooms + a queen sleeping loft, 2 full en site indoor bathrooms, one half off common room, 3 massive outdoor bathrooms, new central AC, multi-zone hi-fi, x2 two-person soaking hottubs. Fireplace, propane and charcoal grills, fiberoptic internet at blazing 500mbps! Only 6 mins to Montauk or Amagansett. Short walk to jitney stop.

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.

5 out of 5 average rating, 20 reviews

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 ⛱

4.87 out of 5 average rating, 113 reviews

A spacious living area features exposed wooden beams and a cozy brick fireplace. Comfortable seating includes a brown sofa and recliner, with decorative pillows adding warmth. A glass coffee table stands on a colorful area rug, while large windows overlook the greenery outside.

Cabin in North Fork

Beach & Woods: Cozy Cabin, Hot tub, Peloton, Oh My

Welcome to nature's retreat, our secluded North Fork haven where 2+ acres of wild beauty and private beach access promise unparalleled relaxation. Delight in our hot tub's warmth under the stars, unwind on swings, or glide on bay waters with our kayak. With enchanting porch views, an invigorating outdoor shower, and nearby organic farms, our cabin is an idyllic escape. Experience the local charm with vineyard tours and return to a haven of comfort and adventure.

Popular amenities for Sag Harbor beachfront rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly beachfront home rentals

4.94 out of 5 average rating, 51 reviews

A serene waterfront scene is presented, showcasing calm blue waters extending towards the horizon under a clear sky sprinkled with a few clouds. The sandy shoreline gently curves along the edge, bordered by sparse greenery for a peaceful coastal ambiance.

Home in Mastic Beach

Mastic Beach Surf House

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

5 out of 5 average rating, 4 reviews

Southold Beach House

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

A tranquil view of Gardiners Bay is visible through a window, framed by green glass vases and a large pitcher. The sunset casts soft colors across the water's surface, with grassy areas and trees lining the horizon.

Cottage in The Hamptons

4.86 out of 5 average rating, 28 reviews

Waterfront Cottages Gerard Drive

An outdoor seating area is showcased with a wooden picnic table shaded by a large striped umbrella. Two green chairs are positioned nearby, set against a backdrop of lush greenery and a clear view of the bay. Blue skies and gentle waters enhance the serene setting.

Home in South End

5 out of 5 average rating, 5 reviews

Charming, waterfront beach house

A spacious bedroom features a queen size bed with gray linens. Natural light floods the room through large glass doors that open to scenic views. A comfortable chair and side table complement the space, while a textured area rug enhances the warm wooden flooring.

5 out of 5 average rating, 8 reviews

North Fork Waterfront Log Cabin

Beachfront home rentals with a pool

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, 82 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 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.

Cottage in The Hamptons

5 out of 5 average rating, 16 reviews

Bayfield Farms Country Estate Guest House

Apartment in Greenport

Waterfront Renovated Duplex

Superhost

The image presents a coastal view featuring a well-maintained property adjacent to the shoreline. The sky displays a gradient of colors at sunset, and gentle waves can be seen lapping against the rocky beach. Surrounding greenery complements the tranquil setting.

4.83 out of 5 average rating, 30 reviews

North Fork Sound Front Home with Pool

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!

4.88 out of 5 average rating, 103 reviews

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.

Condo in North Fork

Waterfront Condo C-204 at The Cliffside Resort

Superhost

Home in East Hampton

Charming East Hampton Home, Private Heated Pool

Private beachfront home rentals

5 out of 5 average rating, 30 reviews

A cozy cape house is situated on a knoll, featuring a front porch with large windows. The gray shingle exterior complements the lush green lawn, which is bordered by tall grass. Trees and shrubbery frame the property, enhancing the natural surroundings.

Cottage in The Hamptons

Traditional Cape on Gardiner's Bay at Fresh Pond

4.97 out of 5 average rating, 34 reviews

A wooden dock extends into calm waters, surrounded by lush green reeds and grasses. A boat can be seen gliding across the water, with trees lining the background, creating a serene natural setting.

Home in Mastic Beach

Mastic Beach Waterfront Designer Retreat

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

A sandy beach stretches along the shoreline, meeting calm blue waters under a clear sky. A wooden staircase leads down to the beach, surrounded by sparse vegetation and rocky areas. Soft clouds drift above, contributing to a serene coastal scene.

4.91 out of 5 average rating, 35 reviews

Pumpkins & Sunflowers! Cozy Cottage in the Fall!

An open-concept living space is visible, featuring a sizable kitchen island with a granite countertop. A dining table is set for six, surrounded by elegant chairs, while large windows provide a view of the water. Soft drapes frame the windows, enhancing the airy atmosphere.

Home in South End

4.93 out of 5 average rating, 15 reviews

Beachfront - endless sunsets, sandy beach, sunroom

Home in Calverton

4.8 out of 5 average rating, 5 reviews

Cozy hose next to the water

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, 198 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.