luxury house for rent Shelter Island, United States

Enjoy a beautiful airy and bright mint condition Bay Front Orient Contemporary home, perfect for relaxing and entertaining. This 4-bedroom 4.5 bath home has gourmet kitchen, fireplace, open common space for easy entertaining. First floor has access to bay side screened porch from living room and den (or 4th bedroom with full bath). Second floor master bedroom and a guest bedroom open onto upper bay side deck, a third bedroom with full bath completes the layout. Private stairs to the beach and deeded beach rights to association Bay beach just a short walk from the house. Property is close to all village amenities: Country Store, Post Office, Marinas, Bay and Sound beaches. Offered Apr $10,000; May $12,000; June $15,000; July $35,000; Aug $35,000; Sept $20,000; Oct $15,000; Nov $10,000. Permit# 1020.

Relax and enjoy this beautifully appointed bay front house w/ private beach and stunning views of Orient Harbor, Bug Light and Shelter Island. Moor your boat in the bay; kayak, swim, fish or chill on the decks and porches. Basement game room w/ Ping-Pong, TV and games. Conveniently located near shopping, restaurants, ferries, farm stands, vineyards.

Impeccably restored 19th Century gem located in the heart of Orient Village with bay views. Close to bay and sound beaches, and a stroll to all village amenities. Featuring 2 parlors, 3 bedrooms, library, office, eat-in kitchen, updated baths, charming garden, out-door dining, and grill, out-door shower. Offered May $7,000; Aug 12-26 $10,000; Sept $10,000; Oct $7,000; Nov $6,000. Permit #0483.

Classic contemporary style New Construction in the heart of Greenport Village. This 2900+ sqft offering features 4 wide white oak hardwood floors throughout w/ inviting Great Room, eat-in Kitchen and Junior Suite bedroom on Main Level. The second floor features an cozy additional den/media room with two generously sized guest bedrooms sharing a full bathroom, laundry, ample storage, a primary ensuite bedroom with walk-in closet and large walk-in shower. In addition to the 1st and 2nd floors is a partially finished basement with separate outdoor access already in place or as lower level gym or media room. For those looking for tremendous value and as central Greenport Village location, this is an absolute must see.

Not available for year round rent at this time. Newly renovated three bedroom, two bath bungalow just outside of popular Greenport Village.This house provides a sense of privacy and relaxation close to the beach. Located less than one mile away, the captivating Rocky Point Beach is a picturesque retreat for everyone to enjoy. Additionally, there is the exquisite Truman's Beach nearby, which provides a stunning view of Connecticut. Lavender Bay and Sep's Farm are conveniently located only 0.4 miles away.The exterior of the property is designed for entertainment, featuring a spacious patio, barbecue area, fire pit, and even an outdoor shower to refresh after a dip in the nearby beaches.

Summer 2024 Rates: May24-June30 $20K, July2-Aug1 $30K, Aug2-Sept3 $35K, Sept4-Oct4 $15K: Rare new construction on a quiet side street in Greenport Village, this modern luxury home is the perfect base to explore the beaches, wineries, and farm-to-table dining of the North Fork. Walking distance to downtown Greenport and a short drive from all the major North Fork sights. Or just whittle away your days enjoying the amenities of your luxurious home retreat. Lounge in your heated saltwater pool while sipping a cold drink. Curl up with a book in front of your gas fireplace. Catch up on sleep surrounded by plush bedding on your memory foam mattress. Immerse yourself in the low-key North Fork lifestyle at your private Greenport Getaway.

A welcoming first floor with beautiful natural light from the giant sliders welcoming you to the deck with a large and heated pool. Enjoy the privacy protected by lush green trees and bring relaxation to the next level. Upstairs you will find two good sized bedrooms with a shared bathroom. With the outdoor oasis, you likely won't be spending too much time indoors, but if you choose to you will be as comfortable as ever. Washer and dryer are available in the basement so you never have to leave this gorgeous set up!

Magical 1840's Cottage in Browns Hills with endless views across Orient Bay. Beautiful south facing garden abutting farm fields. Three bedrooms 1.5 baths, outdoor shower, deeded sound beach. A private, tranquil natural sanctuary in bucolic Orient. Offered July $15,000; Aug $15,000; Sept $8,000; year-round, furnished starting Sept $32,000/mo. Permit #0308.

Situated in a charming and serene neighborhood in Greenport and located just minutes from both Greenport Village and Southold Town Beach, this recently updated Cape offers 1,500 sq. ft. with 4-bedrooms, 2-baths and a spacious living area that flows seamlessly into a bright and airy eat-in kitchen. A full, unfinished basement leads out to an expansive, fenced backyard, and the attached 1-car garage and driveway capable of accommodating 2 additional vehicles ensures sufficient parking for tenants. Don't overlook the opportunity to rent this gem! Please note that the reported square footage is an approximation as the Town of Southold does not have records of the square footage for the second half story.

Amazing North Fork home with heated salt water gunite pool located in Grandview Estates featuring 4 bedrooms (1st floor bedroom with ensuite, 2 ensuite guest bedroom on the second floor with 1 additional guest bedroom and guest bathroom) office/den also located on the second floor with a large sitting area and balcony at the landing of the second floor, large, finished basement with projection TV. Available October, November, and December for 2-week minimum period for $3,000 per week. Permit #0441.

Experience breathtaking views of Long Island Sound and Orient Point County Park from this spacious open-concept home. This beautifully updated 4-bedroom, 4-bathroom residence offers a private 20x40 heated saltwater in-ground pool and serene backyard. Host memorable gatherings in the spacious kitchen, perfect for indoor and outdoor dining. The expansive master suite boasts breathtaking views, a king-size bed, an office nook, dressing area, a full bathroom, and a private balcony. The lower level features a cozy sitting and entertainment room, an exercise room, a full bathroom, laundry facilities, a 2-car garage, and direct access to the pool and backyard. Enjoy easy access to the pristine sound beach, hiking trails, Orient State Park, and Duryeas restaurant. Located at the tip of Long Island, this exceptional home is perfect for anyone seeking coastal living with ample entertainment and relaxation space. Permit# 0234. Offered Apr $11,000; May $20,000; June $25,000; Sept 5-30 $25,000; Oct $20,000; Nov $15,000.

Here's the perfect home for year-round living or summer enjoyment! Sited on a beautifully landscaped 1+/- acre in the Northwest Woods that's convenient to East Hampton Village and bay beaches, this lovely property boasts 4 bedrooms, 2.5 baths, and much more. The living room and dining area with cathedral ceilings and skylights create a bright and airy space with wood burning fireplace and glass doors opening to the heated pool and entertaining deck. The house also boasts a generous eat in kitchen and first floor primary suite with 3 guest bedrooms upstairs and a full basement. The perfectly positioned heated pool has an electric pool cover and is surrounded by spacious decking set among flowering shrubs and mature trees to create an ideal spot for relaxing or entertaining. The house also comes with a generator to set your mind at ease should a storm or accident cause a power disruption. Nicely location close to Three Mile Harbor and bay beaches, and short drive into the Village of East Hampton. [[Rental Registration # 22-1276]] EH RR #: 22-1276 Rental Terms: Winter Season: $25,000 Per Month

Also available Nov 1 - Apr 30 $36K This beautiful waterfront home in Sag Harbor is now available for rent for the first time. Sweeping views of the Little Narrows section of Sag Harbor abound and are afforded from many areas of the property. Highlights of the first floor include a large living and dining area that overlook the water, a separate kitchen, a charming study surrounded by windows, a guest room and hall bath. Upstairs is another guest room and bath and the primary suite, which has its own bath, a private veranda and is surrounded by windows and expansive water vistas. The backyard has a covered porch, an outdoor shower, a large deck and a long dock out to the bay, which is wonderful for boating, kayaking and even a swim. This waterfront gem is very close to Sag Harbor Village and its many wonderful parks, shops and restaurants. Rental Reg. # RP230721 Reg. Expires 6/15/2025 EH RR #: RP230721 Rental Terms: Winter Season: $33,000 Per Month Two Weeks: $35,000 August - Labor Day: $60,000

Welcome to your dream retreat! This distinctive older home boasts five thoughtfully designed levels, offering an abundance of space and character. Each floor presents a unique ambiance, perfect for both relaxation and entertaining. Key Features: Private Primary Suite: Enjoy the ultimate sanctuary with a spacious primary suite, complete with a cozy sitting area, ample closet space, and an en-suite bathroom for your convenience. Open Living Areas: The main living level features large windows that fill the space with natural light, showcasing beautiful architectural details and providing stunning views of the surrounding landscape. Versatile Spaces: With multiple levels, you'll find areas perfect for a home office, gym, or guest suite-tailor the spaces to suit your lifestyle. Outdoor Oasis: Step outside to discover your own private paradise! The swimming pool is ideal for summer gatherings, while the surrounding patio provides a serene setting for lounging or alfresco dining. Charming Details: Original hardwood floors, intricate moldings, and vintage fixtures add a touch of history and charm throughout the home. This property is just minutes away from a private HOA beach, local amenities, and parks. Don't miss your chance to rent this unique home that combines character, comfort, and a fabulous outdoor space for the summer of 2025!

This just renovated ranch centrally located in Springs offers and incredible stay to its guests. An outdoor shower to cool down from the beach just down the road, a large lawn space for hanging in the evening, and a wonderful deck with a grill to bbq. Thats not all, the inside of this house is immaculate and the layout phenomenal. You will never want to leave this modern gem.

This 3 Bedroom, 2 bathroom, modern home is the perfect centrally located Hamptons getaway! A private home nestled into a quiet and friendly neighborhood in close proximity to bay beaches, a few marinas, great hiking trails, and amazing waterfront restaurants.

Welcome to your new sanctuary! This beautifully designed split-level home offers 4 spacious bedrooms and 3 modern bathrooms, perfect for families or those seeking extra space. As you enter, a few steps past the kitchen you'll be greeted by a bright and airy living area that flows seamlessly into the dining space and back into the kitchen, ideal for entertaining. The kitchen is fully equipped with contemporary appliances and ample storage, making meal prep a breeze. Upstairs, you'll find generously sized bedrooms with large windows, providing plenty of natural light. The primary suite features an en-suite bathroom for added privacy. Head downstairs to discover a cozy family room, perfect for movie nights or playtime. An additional bedroom and bathroom on this level adds convenience for guests and separation for those staying over. The large backyard is perfect for summer barbecues, gardening, or simply enjoying the outdoors. There's plenty of room for kids to play or for pets to roam freely. Located just moments away from Maidstone Beach, this home is close to parks, schools, and shopping as well, making it a perfect place to call home for the summer. Don't miss out on this gem-schedule a tour today!

Enjoy this Waterfront rental just steps to Goose Creek beach. Easy water access to Goose Creek from this private location, perfect for kayaking and paddle boarding. Features include 3 bedrooms including second floor primary en-suite with water views, 2 additional guest bedrooms, 2 additional guest baths and plenty of living space overlooking Goose Creek. Spacious bright kitchen, dining area with doors to waterside deck where you will experience beautiful sunsets. The perfect retreat for your summer fun or any other time of the year. Close to all North Fork amenities. Permit # 1023

2025 Rates: July $32,500, July-August $67,500 and August-Labor Day $35,000. Brand New Modern Farmhouse Completed in 2021 and located in the heart Hog's Neck in Southold Hamlet. This home features an impressive 20 x 50 heated pool with electric cover, out door shower and sprawling paver patio. The interior is open and airy with Chef's Kitchen outfitted with Thermador appliances, large living room with built in shelving, gas fireplace and formal dining room. All four bedrooms are located on the second level: 1 Primary En-suite, 1 Junior Suite, 2 Guest Bedrooms and Full Hallway Bathroom. You will enjoy being within close proximity to Goose Creek, South Harbor Park Beach and Southold's vibrant business district!