Beach house holiday rentals in Amagansett

4.95 out of 5 average rating, 254 reviews

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 Springs

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 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.

4.95 out of 5 average rating, 61 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.

4.96 out of 5 average rating, 70 reviews

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 Hampton Bays

Best View + Putting Green + Private Beach

Perched high atop 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!

5 out of 5 average rating, 139 reviews

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 Hampton Bays

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).

4.88 out of 5 average rating, 42 reviews

Waterfront Bungalow w/Private Beach on Peconic Bay

Enjoy a variety of activities when staying at this charming bungalow with a private beach on the Peconic Bay. Enjoy the local Vineyards, take a leisurely stroll in downtown Greenport, ferry to Shelter Island, drive to Orient, or discover local hiking trails. Savor the culinary delights at the area's great restaurants, with fresh seafood and farm-to-table dining. Nestled between Greenport and Orient Point, East Marion provides access to all the North Fork has to offer. Rental Permit # 0449

4.82 out of 5 average rating, 51 reviews

Home in Montauk

4-Minute Walk to Secluded Beach - Hither Hills Gem

Sunny, Spacious 2-story Modern House With Partial Ocean Views, Large Backyard, Two Wrap-around Decks upstairs and downstairs, 4-Minute Stroll to Secluded, Quiet Beach. 4-Minute Drive to Town Rustic Setting in Montauk’s Most Exclusive Neighborhood, Hither Hills Weber gas grill for BBQs Teakwood outdoor dining table & eight chairs for your outdoor dining pleasure Plenty of beach & patio chairs AC upstairs and downstairs Non-declaration of guests will result in termination of booking

4.87 out of 5 average rating, 45 reviews

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 Baiting Hollow

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.

4.91 out of 5 average rating, 34 reviews

Home in Southold

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.

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, 65 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!

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.

5 out of 5 average rating, 35 reviews

Hang by the (Chel)SEA

Enjoy a relaxing stay with family and friends at this cozy soundview beach house. Wake up to breathtaking views of the water, where you can go right into the back yard of your very own private beach! Have a morning coffee on the front balcony of the home that overlooks the beautiful marshlands and then spend the day relaxing on the beach, or kayaking in the water! End the evening with a glass of wine on the back deck, that overlooks the water with the most spectacular sunsets!

A spacious balcony extends along the side of the house, offering unobstructed views of the shimmering water. Weathered wooden benches provide seating, while the gentle waves can be observed lapping against the shore in the distance.

4.86 out of 5 average rating, 37 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.