Beach house holiday rentals in Southampton

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.

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).

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

Designer’s home in Sag Harbor

Nestled in Sag Harbor, this elegant 5-bedroom home offers a saltwater heated pool just 2 miles away from the town. A mere five-minute stroll takes you to the Serene Green local farm stand and Long Beach Bay, where you can indulge in swimming, paddleboarding, and witnessing breathtaking sunsets. The chef's kitchen is perfect for culinary adventures, and you can savor your meals either poolside under the charming string lights at the 8-person farm table or indoors at the 8-person table

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!

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.

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).

Near Beach & Sag Harbor in the Heart of Hamptons!

In the heart of the Hamptons, house with cathedral ceiling near bay beach. Spacious living room, comfy Southwest decor, eat-in-kitchen, washer/dryer, wifi, on a quiet cul-de-sac street, organic lawn, near a great beach. 2-3 bedrooms available. Drive into SAG Harbor, Southampton or East Hampton for dining, shopping, sightseeing, plus gorgeous, award-winning ocean beaches. No smoking inside this home; no pets

Roy's Cottage

Kick back and relax in this calm, stylish space on one of the Hamptons most unique streets. Surrounded on three sides by water (with a town beach at the end of the road), this little house sits directly on Davis Creek and the house comes with a kayak! The small house is perfect for a couple (or a couple with child) but sleeps up to 4 for the weekend guests. Enjoy outdoor life on bucolic Towd Point!!