Beach house vacation rentals in Southampton

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.

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.

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, 68 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. Below are amazing features you can look forward to during your stay: • In-ground Heated Pool w/lounge chairs • Outdoor Shower • 3-Burner Weber Grill • 1 Acre Yard fully fenced in that is child-friendly • Beach Bicycles • Bay Beach Access • Minutes from the ocean beach (Ponquogue Beach)

4.98 out of 5 average rating, 220 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

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, 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 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.

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).

4.89 out of 5 average rating, 27 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.

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,

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.

5 out of 5 average rating, 29 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!

Superhost

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.

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.

A spacious living area features a white sectional sofa and leather armchairs, arranged to face large glass doors that provide views of the beach. Natural light fills the room, highlighting warm wood paneling and a cozy, inviting atmosphere. A dining table is visible in the background.

5 out of 5 average rating, 14 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 ⛱

4.98 out of 5 average rating, 100 reviews

Sea Roost

This private, two-cottage property contains a few of the last remaining original fisherman cottages at Hither Hills built in the 1940s. Set on a lush, private knoll - South of the Highway - Sea Roost boasts mature landscaping and is located steps to Montauk's quiet and secluded Hither Hills Beach. The property consists of a 2 bed/2 bath cottage with separate artist studio (Qn bed, kitchenette & full bath). Dogs negotiable with pet fee. IG @searoosts