luxury house for rent Shelter Island, United States (page 2)

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.

Summer in Orient. Relax on the front porch of this 3 bedroom, 2 bath Ranch in Green Acres, a short walk to association Sound beach & Orient State Park. Open floor plan with updated kitchen, wood burning fireplace & rear deck off dining area - perfect for entertaining. Private yard with specimen trees & vegetable garden with automatic sprinkler system. Available June $5,000; July $8,000; August $9,000; September $4,000; MD-LD $22,000. Permit # 0208

Square footage is approximate as Town of Southold does not have square footage of second half story recorded.

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.

Spacious & immaculate Sound front Contemporary home sitting on a hilltop in Orient, overlooking Long Island Sound to the north & farm fields to the south. Meticulously renovated & professionally designed 4 bedrooms, 5.5 baths with 128 ft of private beach. The ground floor has a large family room with glass doors to a blue stone patio, lawn, & stairs to the beach. This level includes an ensuite bedroom, additional full bath, Malm fire drum, & infra-red sauna. The main floor offers an open floor plan with living/dining/den/kitchen, a 2-sided fireplace, new kitchen, new baths, waterside & farm view decks. A professional ping-pong table, CAC, & outdoor shower are additional amenities. The panoramic Sound and farm views on 1.84 acres offer unique privacy. Offered July 65,000; Aug 75,000. Permit# 1059.

This recently renovated home is an excellent blend of village charm and modern amenities. Located one block from Haven's Beach and a five-minute stroll from the village center, this historic house has a gracious open floor plan that is ideal for summer entertaining. The large open kitchen has an easy flow to the outdoor mahogany deck, tastefully landscaped backyard and 10'x40' heated gunite saltwater pool. The master bedroom features an en-suite bathroom with large glass shower and radiant heated floors. A Juliet balcony overlooks the backyard, complete with its own fruit-producing peach tree. Two additional bedrooms and a recently added fourth bedroom/den on the first floor combine with additional amenities, including a large mudroom, a double set of washer/dryers, three-zone central A/C, a wood burning fireplace, and a 50 HDTV. The dual benefit of a secluded location and proximity to town complete this Sag Harbor Village gem. EH RR #: R-24-0004 Rental Terms: Winter Season: $45,000 Per Month September: $30,000 August - Labor Day: $65,000

Step into summer in Orient this year. Relax and rejuvenate in the quiet soundfront beach community of Orient by the Sea. The sunny open concept floor plan with sliding glass doors leads out to the covered backyard deck and invites indoor and outdoor entertaining. Just a short drive away to Greenport's many restaurants, the area's popular wineries for a tasting, or take a bike ride to Orient Beach State Park for a peaceful day on the bay. Permit #0863

2024 Rates: June $6,250/week or $25K/month; July $8,125/week or $32,500/month A1-LD $8,750/week or $35K/month. Experience North Fork summer living in this newly introduced gem! Nestled in the sought-after Eastern Sterling Shores community, this impeccably designed modern farmhouse offers exclusive access to a private Long Island Sound beach. Step inside to discover a light-filled and meticulously styled interior adorned with contemporary finishes and furnishings. The heart of the home is the chef's kitchen seamlessly integrated into the Great Room and anchored by a cozy gas fireplace. On the first floor, you'll find a convenient half bath, a junior en-suite bedroom, a spacious mudroom, and a sizeable 2-car garage. Ascend to the second level to encounter two additional guest bedrooms sharing a full bathroom, along with a stunning primary en-suite bedroom. The primary bath boasts a luxurious double vanity, a walk-in shower, a soaking tub, and an expansive walk-in closet for added convenience and indulgence. Outside, the property showcases a captivating landscape featuring a sprawling stone patio enveloping a 20x40 heated salt-water pool, complemented by an outdoor shower - an ideal setting for hosting gatherings and enjoying the summer sun.

2025 Rates: MDW-LD $142,500; June $30K; July $52,500; A1-LD $55K. This Modern Hamptons style home offers everything you could ask for from a Summer retreat to the East End. Featuring over 3500sqft of living space, the impressive Great Room is the centerpiece of the house and flows seamlessly to the rear yard which features a 20x40 heated gunite pool with sun deck, large architectural stone patio w/ fire-pit and large gas fired grill. In addition, you will enjoy lazy summer walks to the Rock Cove Estate community private Sound side beach and peak-a-boo water-views from the second floor. All bedrooms are generously proportioned but the Primary En-Suite is truly spectacular with high vaulted ceilings, private waterside balcony, walk in closet and En-suite full bathroom. Bonus feature, the second floor offers a game/media-room w/ full-size pool table, shuffle board table and waterside balcony. Don't let this amazing offering slip away!

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

Escape to a charming 3 bed, 2 bath Sag Harbor rental for an off-season retreat. Open living and dining area, fully equipped kitchen, and cozy bedrooms offer comfort and relaxation. Modern amenities, including a fireplace, ensure a cozy stay. Explore the historic village's boutiques and dine in its renowned restaurants. Take leisurely strolls by the waterfront Located 1 mile from Foster Memorial Beach (Long Beach) and 1/2 mile from Sag Harbor Village. Experience Sag Harbor's allure in this inviting rental.

Escape to this 4 bedroom, 3 bath waterfront North Fork Retreat with expansive views across Hashamomuck to Peconic Bay. The back yard features a deck with private stairs leading down to the water, perfect for kayaking and paddle boarding. End the day entertaining around the fire or with a sunset stroll on your deeded Long Island Sound beach just a block away. Make this home your jumping point to enjoy the beaches, parks, restaurants, vineyards, farm stands, golf courses, and the many other activities the East End has to offer. The list is endless and is awaiting your arrival! Rental Permit #0477

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.

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

Diamond contemporary, 4 bedrooms, 3.5 bath, full basement, LR, DR, EIK, IGP, Pool house, won't last!!

This privately located home is waiting for you to come spend some time this summer! Just minutes away from the Village of Sag Harbor, restaurants and the bay beaches, this home features 4 bedrooms, 3.5 baths with an open concept. The main floor offers a master bedroom with master bath, a beautiful kitchen, dining and living room, as well as a family room with a fireplace and a powder room. The second floor includes 3 bedrooms, 2 full baths. The basement is finished with gym equipment, den/office area. Outside is your beautiful deck with plenty of room for entertaining, a hot tub and heated in ground pool.

2024 Rates JULY 32,500 Brand New Modern Farmhouse Completed in 2021 and located in the heart Hog's Neck in Southold Hamlet. This home features an impressive 20x50 heated pool w/ electric cover, out door shower and sprawling paver patio. The interior is open and airy w/ 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!