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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 charming cottage is set against a backdrop of lush greenery, featuring a welcoming front porch with a white railing. Natural light illuminates the exterior, showcasing the textured shingle siding and a gabled roof. The grassy area extends toward the tree line, creating a serene atmosphere.

Home in The Hamptons

4.95 out of 5 average rating, 247 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.

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, 219 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, 236 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 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, 50 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.

A vibrant sunset reflects on calm waters, with shades of orange and purple illuminating the sky. Silhouettes of small boats are visible along the sandy shoreline, while gentle waves create a serene atmosphere. The scene offers a tranquil view of Long Island Sound at dusk.

Home in East Shore

4.95 out of 5 average rating, 121 reviews

Beach Haven - waterfront, near Yale, sunsets

Everything you need for an amazing vacation, year-round, in our comfortable home right on the beach! Walk out the back door and dip your toes in the sand and in Long Island Sound. Enjoy spectacular views from the back patio, sun room, and most rooms in the house. Watch the sunset while soaking in the hot tub. Sit by the gas fireplace with a book. Stroll along the lovely nearby sea wall. 10-minute drive to Yale and all downtown New Haven has to offer. 5-minute drive to Lighthouse Point Park.

Top guest favorite

A wooden deck area features a dining table with six chairs, accompanied by a grill. A large umbrella provides shade, while the picturesque view of the water and distant marina is visible beyond the railing, set against a clear blue sky.

Home in The Hamptons

5 out of 5 average rating, 137 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).

Top guest favorite

An open-concept kitchen and living space features modern appliances and a wood-topped island with seating for three. Light cabinets and blue walls create a bright environment, while a hallway visible in the background leads to the entrance of the cottage.

Home in Branford

4.98 out of 5 average rating, 178 reviews

“The Lighthouse” A Beach Cottage by the Sea!

Relax at this unique and tranquil getaway. Long Island Sound to the left, hiking trails to the right. Come kick your feet up at this quiet dead-end road. Enjoy all the modern amenities in this gem of a cottage community. Restaurants and nightlife are just a quick stroll away. Avoid roadside hotels and take a vacation for a night, week, or longer! Check in anytime and at your convenience!No keys to lose or to return! This property provides secure, keyless entry with an August Smart Lock!

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

4.89 out of 5 average rating, 27 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.

Top guest favorite

Home in The Hamptons

4.98 out of 5 average rating, 103 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,

Home in Saybrook Manor

4.91 out of 5 average rating, 46 reviews

Romantic Couples Retreat with Private Sandy Beach

Get ready to relax and unwind! Old Sea Lane Cottage is located in a peaceful quiet setting in Old Saybrook’s premier Indian Town Association. Tucked away on a dead end street, this cottage is home to your own private beach. Catch the sunrise and sunsets. During low tide, swim or paddle board across the water to Harveys Beach. You will never get tired of watching the birds and hearing the sounds of nature! This is a truly special location. INQUIRE ABOUT OUR EVENT FEE. No pets

A wooden walkway leads to a serene beach, with gentle waves lapping at the shore. Natural vegetation frames the pathway, and the expansive ocean stretches beyond, meeting a clear blue sky. The coastal landscape provides a peaceful atmosphere.

Home in North Fork

4.88 out of 5 average rating, 24 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.

Vacation rentals for every style

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Popular amenities for Greenport beach house rentals

Free parking on premises

Air conditioning

Beach house rentals with a pool

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

A heated lap pool is set within a wooden deck, surrounded by lush greenery and a large tree with vibrant red leaves. Two sun loungers are positioned nearby, inviting relaxation under the sun, while soft deck planks create a warm and welcoming atmosphere.

Home in Brookhaven

4.88 out of 5 average rating, 8 reviews

Brookhaven Beach Design Retreat - Pool Update 2025

A spacious outdoor area features a private pool with a wooden deck, surrounded by lounge chairs and a sandy beach area. The home is visible in the background, complemented by lush greenery and a clear blue sky.

Home in The Hamptons

3BR/2BA: beachfront, pool, hot tub, outdoor dining

An aerial view captures the unique structure of the waterfront home, surrounded by rocky landscapes and water on three sides. A pool is seen in the backyard, bordered by landscaped greenery, alongside a small beach area and a pier extending into the water.

Home in Branford

4.92 out of 5 average rating, 26 reviews

Breathtaking Panoramic Waterfront

Home in The Hamptons

Breezy Bay

An outdoor pool gleams under a bright blue sky, surrounded by a spacious wooden deck. The inviting water reflects sunlight, while distant views of natural surroundings and the bay are visible in the background.

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 stone pathway leads up to the entrance of the cottage, bordered by vibrant pink and white flowers. Lush greenery frames the scene, complemented by decorative lanterns, creating an inviting approach to the home.

Home in Guilford

4.95 out of 5 average rating, 75 reviews

Scenic Mulberry Point Connecticut Beach House

A charming beach house is positioned directly on the shore, featuring multiple levels and a wrap-around deck. The lower level showcases a stone wall that outlines the sandy area, while the surrounding landscape includes beach grass and distant homes.

Home in Madison

4.83 out of 5 average rating, 12 reviews

Sea La Vie - Beachfront Private Home

A vibrant sunset is visible through a window, casting a warm light over a calm bay. The sun reflects on the water, and silhouettes of trees frame the scene, creating a serene coastal atmosphere.

Home in The Hamptons

4.95 out of 5 average rating, 96 reviews

Stunning Bay-front Views - Hampton Bays

A bright living space features large windows providing panoramic views of the Long Island Sound. A cozy sectional sofa with decorative cushions faces a minimalist gas fireplace, while a wooden coffee table sits nearby. The open layout connects to the dining area and kitchen, enhancing the coastal ambiance.

Home in Westbrook

5 out of 5 average rating, 13 reviews

Adults Only Toes In The Sand Beachfront Charmer

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.

Home in The Hamptons

4.79 out of 5 average rating, 33 reviews

Historic East Hampton Home - Private Beach Access

A spacious outdoor deck overlooks the tranquil waters of Long Island Sound, featuring comfortable lounge seating and a fire pit. The serene beach is visible in the background, framed by lush greenery, inviting relaxation and outdoor gatherings under the open sky.

Home in Morgan Point

4.91 out of 5 average rating, 57 reviews

Oceanfront Getaway - Quiet, Firepit + Pvt Beach

Home in Old Lyme

5 out of 5 average rating, 27 reviews

BEACH FRONT COTTAGE OVERLOOKING THE SOUND

A covered deck features several wicker chairs with turquoise cushions, providing an inviting space to relax. The expansive waterfront view showcases the beach, with gentle waves lapping at the shore. Natural light filters through the open railings, enhancing the serene atmosphere.

Home in Westbrook

5 out of 5 average rating, 5 reviews

Dreamy Waterfront Westbrook Home on Private Beach

Pet-friendly beach house rentals

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 view of the private beach from the home, showcasing a clear blue sky above. A pathway winds through lush green grass towards beach chairs and an umbrella. Duck Island is visible in the distance, highlighting the serene coastal setting.

Home in Westbrook

4.84 out of 5 average rating, 51 reviews

Duckling Crossing | Beach House on the Sand

An open living area features a light-colored wooden floor, with a cozy gray sofa adorned with dark blue cushions. A round, wooden coffee table is positioned in front. A mirror and framed art decorate the walls, while a ceiling fan offers a gentle breeze.

Home in Saybrook Manor

4.83 out of 5 average rating, 24 reviews

Seas the Day at the CT Shoreline

Top guest favorite

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.

Home in The Hamptons

4.98 out of 5 average rating, 51 reviews

Best View + Putting Green + Private Beach

A vibrant sunset is captured over calm waters, with hues of orange and pink reflecting on the surface. Fluffy clouds are scattered across the sky, adding depth to the serene atmosphere. The shoreline is visible in the foreground, gently meeting the water.

Home in The Hamptons

4.86 out of 5 average rating, 44 reviews

2-Bedroom Private Suite, close to Montauk

A dining area is showcased with a round table surrounded by four teal chairs. Large sliding doors reveal bay views, framed by sheer white curtains. A rug with black and white stripes lies beneath the table, complementing the light hardwood flooring and wall-mounted artwork.

Home in Shirley

4.96 out of 5 average rating, 48 reviews

Waterfront Designer Stay • Sunsets • Near Beach!

The exterior of a three-story home is highlighted, featuring a balcony on the top floor and large windows that provide ample natural light. Two lounge chairs and a small table are positioned on the sandy ground in front of the house, inviting relaxation.

Home in Madison

4.89 out of 5 average rating, 53 reviews

Coastal getaway with water views in every room

Top guest favorite

A spacious outdoor deck features a dining set with blue chairs and a large umbrella, offering shade. Nearby, blue beach chairs and umbrellas are arranged on the sandy beach, with a kayak resting beside them, all set against a serene waterfront view.

Home in North Fork

5 out of 5 average rating, 29 reviews

Hang by the (Chel)SEA

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