Beachfront vacation rentals in Sag Harbor

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.

Hamptons Beach House- Sun, Sand & Relax-Beachfront

This beautiful Hamptons beachfront home is right on Shinnecock bay with your own sandy beach right in the backyard! Relax with your toes in the sand or go for a swim. Located just 4 min. by car from the main town for all your shopping needs. My place is also within walking distance to one of the Hamptons best waterfront Caribbean restaurants- so no worries about having a drink and getting home. The location and ambiance is what makes my place stand out from the rest. You’re gonna love it here!

Incredible 2 Bedroom Waterfront Cottage!

An amazing & unique experience on the North Fork of Long Island. Sitting on a bluff 15’ above our private beach, this 3 season multi-family property boasts panoramic views of the LI Sound. Amazing sunset/sunrise views, fishing, beach combing, swimming, wineries, restaurants, shopping. Huge 2nd story deck for evening cocktails. Full kitchen, BBQ, loads of amenities. Updated inside & out. Private beach shared only with other guests of the property Please note there is some noise from passing cars

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.

Savor Ocean Sunsets at a Soothing Beachfront Haven

Newly renovated and featured as a top Airbnb by New York Magazine, The Beach Cottage has been designed and decorated in a modern organic style, with a palette of whites and neutrals to create a serene and peaceful escape. Relax in the airy, light and open living room, which features a wall of glass for indoor/outdoor living with expansive, uninterrupted water views. Stay on the property for swimming, beach walks, sunsets and BBQs - or venture out to enjoy all the North Fork has to offer.

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.

Hamptons WaterLiving-Dock, Kayak, Beach, EV charge

[FOLLOW US on INSTA @29watersedge] 1-mile from the beach, this child-friendly waterfront Southampton home is a perfect family getaway. Ready for watersports: kayak, paddleboard, boat, or jet ski. Walk down to the beach for a swim in the bay. At home, the backyard has it all: large dock, fire pit, swing/playset, hammock, grill, & oversized deck to take in the views. Surrounded by nature and water, you are just minutes from restaurants and shopping in Southampton Village &Sag Harbor.

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.

Beautiful Waterview Condo on the North Fork of LI

Waterview luxury suite accommodates up to 6 guests with two bedrooms and two bathrooms located on the North Fork of Long Island at The Cliffside Resort Condominiums in Greenport, New York. This location is minutes from town as well as wineries and centrally located to the ferry which can take you to Shelter Island and the South Fork. The resort is well maintained with a pool , BBQ grills and private beach access as well as ample parking for guests.

Hamptons Waterfront Suite | Private Hot Tub

✔ Separate private guest suite with its own entrance ✔ Entire back property exclusively yours (not shared) ✔ Year-round saltwater hot tub ✔ Private dock + 2-person kayak ✔ Fire pit, lounge chairs & beach towels ✔ Stunning waterfront sunrise & sunset views ✔ Private porch & outdoor shower ✔ 55" Smart TV & electric fireplace ✔ Self check-in & central air ✔ 19 minutes to Southampton Village ✔ Adults only – No pets – No children

Historic Home + Private Waterfront Access

A rare piece of East Hampton architectural history. Designed in 1958 by Kaneji Domoto, a student of Frank Lloyd Wright, this mid-century home celebrates indoor-outdoor living with walls of glass, abundant natural light, and panoramic views of Three Mile Harbor. Set among mature trees with a private staircase down to the water, the home offers a truly unique Hamptons experience - from sunrise coffees to unforgettable sunsets.

Waterfront Escape | Private Beach, Pool & Views

Overlooking the Long Island Sound, this beautiful waterfront condo is the perfect North Fork coastal escape. Enjoy peaceful mornings with panoramic water views, spend your days soaking up the sun on the private beach, and unwind on the waterfront deck as the sun sets over the Sound. Located just minutes from Greenport Village, you’ll be close to charming boutiques, local farms, award-winning wineries, and gourmet dining.