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Beach house vacation rentals in Greenport

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Top-rated beach house rentals in Greenport

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Top guest favorite

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.

Home in The Hamptons

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.

Top guest favorite

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

4.98 out of 5 average rating, 224 reviews

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

The exterior of a two-story beach cottage is visible, featuring a soft gray facade and a balcony on the upper level. Large windows illuminate the lower floor, surrounded by a well-kept lawn and garden. A decorative trellis adds character to the welcoming entryway.

Home in East Haven

4.89 out of 5 average rating, 240 reviews

Beach Cottage by the Sea

Beautiful 1920's beach cottage with beach access just across the street. Enjoy the sea breeze, ocean views, and sound of the waves lapping in this quaint home with unique architecture. Ten minutes to downtown New Haven and Yale for great places to eat, museums, and nightlife. Public beach and playground nearby. Warm and welcoming community. Master bedroom has vaulted ceilings and deck with views of the sea. Central Air, Cable TV, outdoor grill, plenty of parking. Enjoy this lovely home!

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

4.95 out of 5 average rating, 57 reviews

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.

A serene waterfront scene captures a vibrant sunset reflecting orange and pink hues on the calm water. Silhouettes of trees frame the view, while the silhouette of a private dock juts out into the bay, enhancing the tranquil atmosphere of the setting.

Home in The Hamptons

5 out of 5 average rating, 22 reviews

Year Round Hamptons Waterfront

Magical year-round waterfront home with private dock, direct access to Peconic Bay & spectacular views in prime Hamptons location. Minutes to Southampton Village & Sag Harbor. Renovated & newly furnished, the house features an open concept kitchen, dining, living room & bathroom on the 1st floor. 2nd floor has 3 bedrooms /2 baths & den /office. Dine al fresco on the beautifully furnished outdoor patio with fire pit. Paddleboards & Kayaks provided & ready to launch directly from the dock.

A tranquil view of a private beach stretches along the coastline, where gentle waves lap against the smooth sand. Soft clouds dot the blue sky, while beach houses stand in the background, providing a serene coastal ambiance.

Home in Morgan Point

4.96 out of 5 average rating, 53 reviews

Direct Beachfront Modern Cottage on Private Beach

A Modern Beachfront 3-Bedroom House RIGHT ON WATER! AT A GLANCE: ➤ 10 seconds to water ➤ Private beach to enjoy swimming, kayaking, and strolls along the Long Island Sound ➤ Fully updated well stocked kitchen ➤ Grill for outdoor BBQ's ➤ Large deck to catch some rays ➤ Outdoor shower to rinse off ➤ New AC units & ceiling fans throughout ➤ Large TV w/ AppleTV connectivity & WIFI ➤ Only 90 min to NYC, close to Yale in New Haven ➤ Hosted by an experienced Superhost ➤ Sorry, No pets allowed.

Top guest favorite

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.

Home in The Hamptons

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).

An open living area features high ceilings and large windows that bring in natural light. A sectional sofa in deep blue surrounds a vibrant orange rug, while an artwork adorns the wall. A dining area with a wooden table and chairs can be seen in the background.

Home in Riverhead

4.85 out of 5 average rating, 41 reviews

North Fork True Beachfront Home

This is New York version of California's Big Sur, with direct beach access and spectacular water views, surrounded by forest. Modern, 3,000 sq feet. Walk down path from house to a fantastic sand beach with lifeguard. Large deck for lounging, BBQ, and sunset views. 4 bedrooms, 3 baths, outdoor shower, 4 person hot tub, 2 person sauna, separate den w/home theater, gym, hammocks, wood burning fireplace. Experience the Long Island Sound without neighbors and the suburbs; a naturalist's haven.

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

4.9 out of 5 average rating, 30 reviews

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.

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.

Home in The Hamptons

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,

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.

Home in North Fork

4.81 out of 5 average rating, 27 reviews

North Fork Sound Front Home with Pool

This Long Island Sound front property on nearly three acres of land with an inground, custom designed, gunite pool is the perfect vacation home. Walk down the ramp to your private beach for a kayak, paddle board or swim in the summer and enjoy a luxurious outdoor shower afterwards. In the fall and winter months, enjoy the extensive book collection and stay cozy by the fireplaces. Spacious and bright, this home has a unique aesthetic and can accommodate 8 guests comfortably.

Top guest favorite

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

5 out of 5 average rating, 18 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 ⛱

Vacation rentals for every style

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Cottages

Quaint homes, peaceful surroundings

Houses

A space thats all yours, with room for everyone

Apartments

Convenient locations with everyday essentials

Popular amenities for Greenport beach house rentals

Free parking on premises

Air conditioning

Beach house 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.

Home in The Hamptons

Bayside Sensation in Southampton

A serene outdoor area features a heated saltwater pool surrounded by well-manicured grass. Two lounge chairs are positioned nearby, providing a perfect spot for relaxation. The house is visible to the left, with a deck leading to the pool, framed by lush trees.

Home in Brookhaven

5 out of 5 average rating, 16 reviews

Beautiful 2 acres, 3 Bd /2 b, Pool, Pets Welcome

Home in East Hampton

New place to stay

Charming East Hampton Home, Private Heated Pool

An aerial view showcases River House nestled amidst lush greenery and serene water views. Large windows reflect the surrounding landscape, while the spacious outdoor area is visible beneath the trees, inviting exploration and relaxation.

Home in Brookhaven

4.88 out of 5 average rating, 8 reviews

Brookhaven Beach Design Retreat w/ Pool

Home in The Hamptons

Breezy Bay

Home in The Hamptons

Bayfront Luxury Retreat with Heated 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.

Home in The Hamptons

4.55 out of 5 average rating, 49 reviews

Steps to the Ocean, Bayside Tranquility, W/Pool!

Private beach house rentals

A wooden staircase leads down from lush greenery to a sandy beach. The path is flanked by trees and shrubs, while a view of the water and beach is visible at the bottom of the steps.

Home in The Hamptons

Exclusive Hamptons Waterfront Getaway

A spacious waterfront home is surrounded by lush greenery and well-maintained landscaping. Large trees provide shade, framing the property. The home features a welcoming façade and is positioned to offer views of the water, with a deck visible for outdoor relaxation.

Home in Rocky Point

3.33 out of 5 average rating, 3 reviews

Waterfront home on Long Island Sound

Home in Shirley

4.92 out of 5 average rating, 51 reviews

Waterfront Designer Stay *Sunsets•Fire Pit•Beach*

A two-story house is elevated on stilts, showcasing large windows that allow natural light to fill the interior. A gravel driveway leads to the house, bordered by flowering plants. Scenic salt marsh views are visible in the background, enhancing the home's inviting presence.

Home in Morgan Point

4.95 out of 5 average rating, 56 reviews

Spectacular Waterfront Home on Private Sandy Beach

Home in Shirley

New place to stay

Bayside Retreat | 2 Bedroom House

A lush, green lawn meets a tranquil bay, showcasing lounge chairs and umbrellas positioned for comfort. The clear water reflects the blue sky, creating a serene backdrop of natural beauty. A pathway leads to the private beachfront, inviting outdoor relaxation.

Home in The Hamptons

Shore Road Serenity

Top guest favorite

A serene outdoor space is presented, featuring red lounge chairs under red umbrellas. A gentle slope leads to the rocky shoreline, where the calm water meets the sky. Soft clouds drift above, and the scene encourages relaxation by the beach.

Home in East Haven

5 out of 5 average rating, 20 reviews

Waterfront Stairway to Heaven!

A green lawn gently slopes towards the water, featuring two lounge chairs positioned for relaxation. A large tree provides shade, while a distant view of the shoreline and an American flag add to the serene waterfront setting under a clear blue sky.

Home in Guilford

5 out of 5 average rating, 29 reviews

Relaxing Waterfront Escape on CT Shore

Pet-friendly beach house rentals

A wooden dining set is positioned on a deck overlooking the water, featuring a large red umbrella providing shade. Tables are set with blue plates, and greenery frames the peaceful view of the inlet and distant seating by the shore.

Home in South End

4.96 out of 5 average rating, 28 reviews

Shelter Bay Cove Waterfront + Beach + spectacular

A wooden table is set for outdoor dining, featuring a range of cheeses, crackers, and fresh fruit arranged on serving trays. A glass of rosé sits nearby, with a view of the ocean visible in the background under a cloudy sky.

Home in Morgan Point

5 out of 5 average rating, 56 reviews

Direct Waterfront Home Located on Private Beach

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

4.98 out of 5 average rating, 46 reviews

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 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.

Home in The Hamptons

5 out of 5 average rating, 8 reviews

Oceanfront Home, Spectacular Views from Each Room.

An outdoor deck features a large dining table surrounded by multiple chairs, shaded by a sun umbrella. In the background, beach chairs and an umbrella are set on the sand, with calm waters extending toward the horizon.

Home in North Fork

5 out of 5 average rating, 30 reviews

Hang by the (Chel)SEA

A cozy living room features exposed wooden beams and built-in bookshelves filled with books. Comfortable seating is arranged around a round table, with a stone fireplace as a focal point. Natural light streams through large windows, enhancing the inviting atmosphere of the space.

Home in The Hamptons

5 out of 5 average rating, 17 reviews

Country Estate and Farm just outside East Hampton

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

Destinations to explore