Holiday rentals in The Hamptons

Serene with large pool ~ 1 block to water + dining

Serene, chic, Hamptons oasis! Enjoy your private home on a quiet street just steps to the water and minutes to Main St. Relax at one of the serene spots on the property, swim in the pool, enjoy the BBQ + firepit! You may spot a deer on the property. Cook in the fully stocked Chef's kitchen and stream on your 80' TV! Walk 1 block to waterfront dining + cafe. Enjoy coffee on the sea, dinner/cocktails watching the sunset over the marina. You'll be 8 mins. to Main St, restaurants and beaches!

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.

Tiny Cottage in Hither Woods, Montauk

A little cabin on our property in Hither Woods. A cozy hideaway conveniently located 12 minutes walk from Gurney's Beach Resort, 16 minute walk from public path to beach, and 6 minutes drive from Montauk town for restaurants and nightlife. Good for couples and solo adventurers, the space is private and homey, with outdoor shower and Chimenea fire pit. The main house is 65ft away, but we honor your privacy. The cottage comes with WiFi, window A/C and complimentary coffee or tea. Parking for 1 car

Hamptons Oceanfront Oasis

Escape the hustle & bustle of city life and unwind at this stunning home in the Hamptons. The oceanfront oasis is the perfect way to wake up to ocean views, beaches and nearby restaurants. Relax on our spacious deck - perfect for morning coffees & sunset cocktails. It is just a short drive to the train station & only 15 minutes from the airport for quick getaways. For your safety, the home is equipped with Ring cameras and one-use key codes. Book now and experience the ultimate Hamptons escape!

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 Star Rated Private Cottage Southampton/Sag Hrbr

The Honeycomb Cottage is a little retreat located on a lush acre of evergreens in Southampton rated 5 Star by every guest that has stayed. One block to Peconic Bay Beach - perfect for a day in the sun. A cozy space with TV, WiFi and Sun Deck. Luxury soaps provided, amazing shower and crisp white linens. Exclusive use of the Hot Tub for Cottage guests. Easy parking and located 15 minutes drive to Sag Harbor or Southampton Village. Koi pond with waterfall will sooth the mind and spirit.

Luxe Southampton Home w/Pool 5 Min Walk to US Open

Enjoy a stylish experience at this centrally-located home. Modern, spacious, airy home with 3 Bedrooms and 3 Bathrooms. Beautiful pool and deck with BBQ. Only 5 minute drive to Southampton Village and Cooper Beach. The perfect Summer escape. Pool is OPEN from May 1st until end of October. Pool can be heated at an extra cost. 5 minute walking distance to Shinnecock Hills Golf Course for the 2026 US Open. One of the closest houses to the course. Unbeatable location. Parking available.

Head of Pond House - Waterfront Cottage

Welcome to the charming, waterfront Cottage at Head of Pond House! Enjoy a peaceful retreat with beautiful lake access year-round and pool access from Memorial Day to October. The cottage features two comfortable king beds, including one in a cozy loft area, a full bath, WiFi, a projector for movie nights, and a fully stocked kitchen. Whether you’re looking for a relaxing escape or a comfortable base to explore the Hamptons, our waterfront cottage is the perfect spot for your getaway.

Designer home in Sag Harbor : 5BR walk to beach

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

Charming Bungalow on the Bay

This newly remodeled 1960’s bungalow is the perfect getaway for couples and families alike. Located right on Gardiner’s Bay, there’s a gorgeous view of the water from the large windows and front porch. From the front steps you can follow the 300 yard path to your own private beach where you can wade, swim, snorkel, paddleboard, or just enjoy the amazing view and salt air. (East Hampton Rental Registry Certificate Number: 24-234)

Sag Harbor Cottage, Walk to the Beach!

Renovated to perfection, this fully equipped fresh & modern beach cottage has an open-plan living room, dining room & kitchen, all with high ceilings, immaculate finishings, & a sunny lower level TV room. A broad mahogany deck with large outdoor shower & gas BBQ grill runs the full length of the house & overlooks a roomy lawn with great privacy, fire pit and mature landscaping.

Dockside 2BR - Prime Location on the Marina Unit B

Morning coffee with boats bobbing out front, dinner next door at Fish House, and lazy walks up to Gosman’s for fudge and harbor views — this is the best of dockside living, Montauk style. Tucked in Westlake Marina, at this fresh, sun-filled 2-bedroom, enjoy comfy beds, a fully equipped kitchen, and easy access to boat charters, seafood, and sunsets.