Beach house vacation rentals in Southampton

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Top-rated beach house rentals in Southampton

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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 East Hampton

4.95 out of 5 average rating, 237 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 bright and airy living area is enhanced by large windows allowing natural light to fill the space. A comfortable white sofa is positioned at the center, accompanied by decorative pillows. Two stylish pendant lights hang above, and a coffee table sits atop a textured rug, creating a welcoming atmosphere.

Home in North Fork

5 out of 5 average rating, 3 reviews

Orient cottage in the Village

Enjoy staying in our newly renovated (2021) country cottage in the picturesque town of Orient, NY. Our lovingly restored cottage has 3 bedrooms and a very comfortable open floor plan with a wood-burning fireplace. Our gourmet kitchen will fulfill your dreams of cooking a delicious meal for friends and family. Upstairs you will find 3 very comfortable bedrooms and 2 baths, one which is ensuite with the primary bedroom. It's a stone's throw away from Village Street, the country store and the bay.

Guest favorite

The exterior of a two-story beach cottage is displayed at night, featuring illuminated steps and strings of lights adorning the railings. A front door painted in a soft blue stands out, while windows above allow glimpses of the home’s interior. Nearby vehicles are parked on the driveway.

Home in Milford

5 out of 5 average rating, 9 reviews

Salty Kisses Cottage Relax

Salty kisses beach cottage is simply adorable. The perfect getaway. Your happy place, always fresh linens, tasteful coastal decor. Direct water views Beach access across street Amazing sunrise and sunsets. At the end of the road is Silver Sands State Park with showers and food. Walk on the boardwalk to Walnut Beach. Live music, milford creamery, bees knees, pizza, lazy lobster and specialty stores. We have a lovely backyard for grilling and chillin. Downtown & Lisman landing only 1-2 mile walk.

Top guest favorite

The kitchen showcases a modern design with white cabinetry and stainless steel appliances. A wooden dining table is surrounded by red metal chairs, while an open layout is enhanced by natural light streaming through large sliding doors leading to the outdoor space.

Home in Montauk

5 out of 5 average rating, 22 reviews

Family Friendly Designer 3bd Centrally Located

Enjoy Montauk for all its pleasures and call this immaculate golf course house your home. Nestled on quiet Fairlawn Drive, you will enjoy a short walk to town, the train station, or the beach. The Manor is just down the street. Take a stroll up to the Fort Hill Cemetery for spectacular sunset views over Fort Pond Bay. If you plan to bring a bike, everything is within biking distance, and plenty is within walking distance. The golf course is just across the street. Rental Registry # 22-953

A hot tub is featured with luminous blue lighting, casting an ethereal glow over the bubbling water. The water jets create dynamic patterns as the surface ripples, inviting relaxation. The surrounding deck area is visible, enhancing the outdoor ambiance.

Home in Hampton Bays

5 out of 5 average rating, 31 reviews

Beach House -Walk to Beach -Live Band -Hot Tub

Fun Beach House with 5 bedrooms, 2 full bathrooms, sleeps 8 adults. 1 minute walk to the entrance of Meschutt Beach & Tiki Joe's Bar & Grill. Live Band on Wed, Fri, Sat and Sun. Fun Hot Tub, Outdoor hot/cold shower. We supply Beach chairs, Towels, Kayak, Weber BBQ grill. Complimentary Coffee and Tea. Close to Dune Road Beaches, Waterfront Restaurants, Wineries, Breweries & Ciderhouse for Beer & Cider tastings. Close to Mini-Golf, Tennis, Pickleball, Golf & Driving Range.

Guest favorite

An outdoor dining area is visible, featuring a glass-top table surrounded by six chairs beneath a large umbrella. A grill sits nearby, with a view of the water and lush greenery in the background, creating a relaxing setting for meals and gatherings.

Home in Hampton Bays

4.98 out of 5 average rating, 113 reviews

Hamptons Beachfront- Relax & Getaway- On the bay

Awesome Beachfront vacation home located directly on a private sandy beach right on Shinnecock Bay. Suntan, swim, kayak or just chill and relax in a float right on the beach in the backyard. Hungry- no worries you can bbq right off the back deck or walk to one of the best Caribbean restaurants in the Hamptons. You’ll love my place because of the location and the ambiance- vacation vibes. My place is perfect for couples, solo adventurers, business travelers, and families (with kids).

Superhost

A spacious living area features a modern sectional sofa adorned with decorative pillows. A large chandelier adds visual interest, while natural light enters through sliding glass doors, revealing a view of the outdoor space. Framed artwork is arranged on the adjacent wall.

Home in Sag Harbor

Newly Renovated Sag Harbor House

Welcome to this newly renovated, charming Sag Harbor house, just a short stroll from the beach and a delightful farm stand. This beautifully decorated home features a cozy yet stylish interior, perfect for relaxation and entertaining. The incredible backyard is a true oasis, adorned with designer landscape and luxurious and comfortable outdoor furniture. Enjoy sunny afternoons by the salt water pool or the fire pit in the evening. This idyllic retreat is the ultimate getaway!

Guest favorite

An elevated view showcases the modern retreat surrounded by greenery. The expansive deck features a pool and hot tub, while covered areas offer shaded seating. Warm lights illuminate the exterior, creating a welcoming ambiance as the sun sets in the background.

Home in Ocean Bay Park

5 out of 5 average rating, 8 reviews

Windows on the Sea ★ Modern Pool & Beach Retreat ★

Welcome to the ultimate retreat just 100 feet from the beach on this quiet Ocean Bay Park block in Fire Island. Modern gut renovation of this 5 bedroom 3.5 bath will be the perfect size for your whole extended family (sleeps 12). High end custom finishes throughout complement some ocean views combined with plenty of thoughtful amenities. Enjoy your own ocean view in our private windowed Modpools Pool & Hot-tub with over 1200 sq. feet of deck. Just bring your bathing suit!

Guest favorite

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

4.93 out of 5 average rating, 40 reviews

Waterfront Designer Stay • Sunsets • Near Beach!

Welcome to The Swan House 🦢🏡 —your peaceful, designer retreat on Bellport Bay. Enjoy stunning sunsets, swans gliding by, and direct water access from the backyard. Relax on the spacious deck, fire up the grill, or take a short drive to Smith Point Beach. Inside, you’ll find an open, sun-filled layout with curated furnishings and a calming coastal vibe. This stylish escape offers serene waterfront living in any season—just 90 minutes from NYC.

Guest favorite

The exterior of a charming two-story carriage house is shown, featuring a light blue façade. A red awning covers a section of the porch, which is framed by large windows. An outdoor dining area with a dark wicker table and chairs is placed on the patio, surrounded by well-maintained grass.

Home in Westhampton Beach

4.94 out of 5 average rating, 72 reviews

In-Town Charming Westhampton Village Beach House

Relaxing and comfortable best describe this perfectly located & recently renovated 1900s Westhampton Beach carriage home - south of the HWY. 2min walk to Main Street. You will be close to everything when you stay at this centrally located home - walk to farmer's market, restaurants, shops, park and beaches. Ideal for a small family gathering or those on the go escaping the city and don't want to drive and be located in town.

Guest favorite

A serene beach scene is captured at sunset, featuring soft, warm hues in the sky blending with the calm water. The sandy shore curves gently along the edge, with distant islands visible on the horizon, creating a peaceful coastal atmosphere.

Home in Sag Harbor

4.95 out of 5 average rating, 20 reviews

Beach Cottage | Steps to Water| Fireplace|Firepit

Kick back and relax in this calm, stylish beach cottage in Sag Harbor. It is the perfect spot for a single or couple to enjoy the Hamptons beachy lifestyle. Fully appointed for your stay, just bring your bathing suit. Outside is your own patio with sitting area, dining table with umbrella, firepit/BBQ area, and my own tiny cottage across the lawn so I (or other guests may be there in August/September/October stays).

Guest favorite

The exterior of the house is shown, featuring large windows that invite natural light. Lounge chairs with green cushions are arranged for relaxation, accompanied by an umbrella for shade. The wooden siding adds a rustic charm, and the surrounding deck offers ample space for outdoor enjoyment.

Home in Fire Island Pines

5 out of 5 average rating, 5 reviews

The DEN-I-ZEN House with Ocean Views - FI Pines

This is the DEN-I-ZEN House in Fire Island Pines. Our home has a communal vibe that offers privacy and space for between 8-10 people. Two rooms have bunks and there are 2 full shared baths in the center of the house. Lounge spaces on two outdoor deck areas plus a platform on the adjacent lot with a hot tub. This south facing home has ocean views and sounds plus sun all day long with a wall of windows.