luxury seaside houses for rent Shelter Island, United States

Charming historic Bayfront beach cottage located on Orient Harbor in Orient Village. Featuring 75 feet of private walkout beach, waterside porch, screen bay view gazebo for entertaining. Interior includes wide plank wood floors, renovated baths, spacious kitchen water view living room with wood burning fireplace, 2 ensuite bedrooms for a total of 3 bedrooms/ 2.5 baths. Walk to Country Store, Post Office, Orient Yacht Club, marinas, and other village amenities. Close to renowned Orient Beach State Park & Cross Island Ferry. Available Aug $35,000. Permit# 1374. No showings until after January 15, 2026.

Sound Front Contemporary Octagonal Home with Private Beach. Contemporary and chic, mint condition 1970's modular octagonal home located on a breath-taking sound front walk-out private beach in Orient. Three bedrooms, each with a full bath and an additional powder room. Updated kitchen and bathrooms. Every room is furnished with period mid-C style furniture. Living room has original Malm wood burning fireplace. Many spacious common areas, including glazed porch connecting the two octagonal wings. Relax on the large water-side deck with hot tub while enjoy panoramic water views from every room. Offered June $15,000; July $35,000; Aug $35,000; Sept $20,000. Permit #0465.

Stunning waterfront shingle style home overlooking Long Island Sound with private beach access. Waterview, heated pool. Wrap-around porch. Original beach stone fireplace, vintage beadboard walls, large, updated gourmet kitchen, open common area, 5 bedrooms, 3 bathrooms, large master ensuite with private screen water view balcony. Beautiful interior furnishings, with teak rocking chairs, chaise lounges and picnic table on porch and pool area for entertaining. Close to Orient Village amenities, marinas, Country store, Yacht Club, and bay beaches. Offered June 3-27 $28,000; Sept 2-16 $14,000. Permit# 1108.

Your quintessential North Fork summer starts here. Tucked away in the quiet beach community of Paradise Shores, this Bayfront cottage is the summer retreat you’ve been dreaming of. Positioned directly on Southold Bay with unobstructed views of Shelter Island, this charming cottage offers the best scenery on the North Fork. Whether you're hosting a sunset dinner or just enjoying a quiet morning, the backdrop is always spectacular. Loaded with vintage charm and coastal energy, it’s a place where the days are measured by the tides rather than the clock. The first floor features a waterfront sunroom, cozy living room, galley kitchen, two bedrooms and a full bath. For ultimate privacy, escape to the second floor, featuring a primary suite with a dedicated sitting area -the perfect perch for morning coffee- and half bath. Step outside to your own secluded paradise where you will find a waterfront deck offering the perfect space for al fresco dining, stargazing, or simply watching the boats pass by. It’s the ultimate front-row seat to the island's beautiful golden-hour. This property has all the markers of a perfect North Fork getaway. Permit #1435. Available Memorial Day-June 30: $18,000, July 1-31: $20,000 and August 1-31: $25,000.

Located just outside Bridgehampton village sits this quiet cottage available for summer and off-season rental. Tasteful amenities include a large living room with fireplace and vaulted ceiling, a separate kitchen with washer/dryer, a dining area, two bedrooms and a full bath. A charming patio allows for outdoor nature enjoyment, all within minutes of local area shops, restaurants and ocean beaches. [[Rental Registration # RP241102]] EH RR #: RP241102 Rental Terms: Winter Season: $30,000 Per Month June: $15,000 Memorial Day - Labor Day: $60,000 July: $25,000 July - Labor Day: $50,000

Find your rental for the US Open at this stunning getaway in Amagansett Dunes! Offering 4 bedrooms, 3 baths with the backyard fully landscaped for privacy. A beautiful gourmet kitchen, dining area, living room with fireplace, den/media room and bedroom are on the first floor, with 3 bedrooms including a primary bedroom suite on the second floor. Situated just one block to the ocean and the community only boardwalk to the beach. Slipping away to the ocean's edge, tucking into the dunes for a bit of sunshine or relaxing in the comfort of this very nice retreat offers one of the most desirable destinations In the Amagansett Dunes.

Single story waterfront home offering 3 bedrooms, 2 baths & South of 27! [[Rental Registration # 241322]] EH RR #: 241322 Rental Terms: August - Labor Day: $30,000 July: $22,000 Other / Short Term - Year Round: $80,000 Winter Season: $4,100 Per Month July - Labor Day: $55,000