luxury real estate for rent Shelter Island, United States

A light, bright and mint condition Orient Village 4 bedroom, 4 bath bayfront home, featuring beautiful classic lines and architectural details throughout. Walls of windows and high ceilings showcase stunning sunsets over Orient Harbor and beyond. Gourmet kitchen, open floor plan with glass doors to outdoor dining area, waterside lawn, two decks and stairs to the water makes this a perfect opportunity for entertaining and family relaxation. Rental includes a gas grill, 2 boat moorings and nearby association sandy beach. This very well appointed home includes an open fireplace, perfect for an extended stay throughout the fall and beyond in an idyllic location that beckons peace and relaxation surrounded by nature and luxury. Nov-March $12,000/mo.; Apr $14,000; May $16,000; June $25,000; July $40,000; Aug $60,000; Sept $60,000. Permit# 0595.

Vineyard Views. Modern Farmhouse on private 1 acre located on the only private, working vineyard in Orient Village. 16 x 32 heated pool, newly renovated chef's kitchen and baths. The home features 3 bedrooms, 3 full baths. Ground floor designed with open common space and designer furnishings for luxurious entertaining, featuring living room with cathedral ceiling with sliders to pool and deck, eat-in kitchen and dining room with sliders to vineyard deck. Den with pull out queen bed, bedroom with queen bed, 2 full baths, laundry and screened porch complete the ground floor plan. Second floor has 2 additional bedrooms; master with king bed, and 3rd bedroom with 2 full beds, and full bath. Amenities include central air, fully stocked kitchen with Aga stove, high speed internet, TVs with streaming video, gas grill. Walk to Village, Yacht Club & steps to a Willow Terrace bay beach. Embrace the North Fork lifestyle. Permit #0516

Impeccably restored and updated 1850's Farmhouse in the heart of Orient Village. Featuring a great room with open floor plan - gourmet kitchen/dining/living room, a second-floor master bedroom with sitting room, full bath, and walk-in closet for a total of 3-bedrooms 2.5 baths in the main house. There is a separate Cottage with kitchenette, bedroom, and full bath, perfect for guests. Lovely private grounds with gardens, grand lawn, and heated salt water gunite pool. Walking distance to all village amenities, beaches, and marinas. Offered June $20,000; July $45,000; Aug $45,000; Sept $25,000. Permit # 1019.

Private, recently renovated, arts and crafts style ranch located in the heart of Orient Village. Three bedrooms, 2 full baths, open kitchen/ living room/ dining room, library, front porch, rear deck with screened outdoor dining area & grilling station. Close to beaches, marinas & village amenities. Offered Aug $15,000. Permit #0505.

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.

Bayfront beach Cottage with panoramic views, stylish & chic. Great room with newly renovated kitchen, dining area, living room, bay side deck. Master bedroom & bath and additional guest bedroom & full bath, outdoor shower, private beach. Offered Nov 2023-March 2024 $4,000/mo.; 2024: Apr $4,500; July $14,000, Aug $16,000, Aug-LD $17,000; Sept $9,000; Oct $5,000. Permit# 0569.

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.

Ithaca's premier luxury patio home community on Blue Heron Way. Newly constructed 2 car garage, 2 bedroom, 2 bathroom center and end units now leasing. No expense spared in creating single level luxury units. Beautiful kitchen with quartz counters, island with custom farmhouse sink, garbage disposals, counter depth fridge, exterior vented microwave range / hood, modern cabinetry and more. 2 full bathrooms, 1 a primary on-suite with walk- in closet, feature quartz vanities, heated ceramic tile floors, comfort height toilets, medicine cabinets and modern sliding shower doors. 2 car garage with automatic door opener offers easy access to additional dry storage via pull down stairs. Mud/utility room with front loading washer and dryer, coat closet and huge pantry. All units fitted with custom cellular shades, solid core doors and glass sliders out to blue stone patios. Energy efficient Mitsubishi heat pump technology along with heat recovery ventilators provide green, low-cost heat and AC throughout. Check out the virtual tour.

Beautifully updated & fully renovated traditional Arts & Crafts home in the heart of Orient Village and one block from Orient Harbor. Gourmet kitchen with Thermador 6 burner/griddle stove, Subzero refrigerator, Bosch dishwasher. Enclosed front porch. Fenced yard, outdoor shower, backyard deck for relaxing, grilling & dining. Professionally landscaped with vegetable garden and outdoor shower. Offered April $9,000; May $10,000; June $16,000; July $25,000; Sept $16,000. Permit #0827.

Charming and chic 3 bedroom, 1.5 bath Cottage on Lake Marion with many charming original features. Open, sunny floor plan with common area that opens onto spacious lakefront deck perfect for relaxing, grilling & dining. Wood burning fireplace, fully equipped cook's kitchen, private dock, outdoor shower, & easy stroll to association bay beach. Offered June $8,000; Aug $16,000. Permit# 0692.

Beautifully appointed townhouse in coveted Stirling Cove Condominiums. Enter a light filled room with magnificent views of the cove and bay. Featuring newly renovated, spacious kitchen, dining room, elegant living room with wood burning fireplace, water view deck, and powder room. Second floor has master bedroom suite with expanded, renovated bath and private water view balcony. A guest room with private bath and laundry complete the floor plan. Unit comes with a private boat slip in the protected basin with easy access to the cove and bay. Complex offers heated in-ground pool, tennis courts, private beach - all just a short walk to Greenport Village restaurants, shopping, and grocery. Near Islands End golf course and access to all that the North Fork has to offer. Full-time on-site management. Jan $5.000; Feb $5.000; March $5,000; Apr $6,500; May $11,000, June $15,000; July $22,000; Aug $22,000; Sept $15,000; Oct $10,000; Nov $7,000; Dec $7,000. Permit # 21-048.

Authentic 1770 Cottage in the heart of Orient Village. Lovingly restored & maintained Village home on beautifully landscaped lot, offering private grounds & distant views of sunsets over the bay. Furnished in period antiques, screened-in porch off kitchen, first floor bedroom. Walk to amenities, bay beach, Yacht Club, marina, farm stand & Jitney. Offered July $10,000; Aug $10,000; Sept $7,000. Permit #0091.

Relax, rejuvenate and recharge in this updated North Fork gem with new kitchen, outdoor deck, screened in porch and large fenced in yard. Three bedrooms and full bath on the 2nd floor. Located on a quiet road but still close to beaches, farm stands and local vineyards! $6,500 per week. 2 week minimum.

Spend your summer enjoying all the North Fork has to offer at this Greenport waterfront home with dock and community bay beach. Completely updated with high end touches throughout including chef's custom kitchen with island, 3 bedrooms (2 are en-suite), 4 full bathrooms, expansive waterfront deck, and a lower level entertainment lounge. The perfect place to relax and unwind.

2024 RATES: JUNE $12,500, JULY $16,000.00 AUGUST $17,000 MD-LD $44,500. Victorian classic in the heart of Greenport Village. Centrally located to all forms of public transportation and close proximity to public Bay beach. This property offers convenience, style and stunning views of Shelter Island and the Peconic Bay. Main features are large front porch, inviting/well appointed living spaces multiple en-suite bedrooms and a large rear yard for entertaining. This historical treasure has been recently updated and provides both the charm of a classic New England port village home and the accommodations of an updated home. Easy North Fork living in Greenport Village.

Beautifully converted 19th C Barn - three story residence with 4 bedrooms, 3 full baths, Eat-in kitchen, deck off living room with sound views, and private beach access. Apr $5,000; May $5,000; June $8,000; July $15,000; Aug $15,000; Sept $10,000; Oct - Mar $4,000/mo; yearly $6,500/mo. Permit# 0774.

Stunning Waterfront shingle style home overlooking Long Island Sound. 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 Aug-LD $55,000; Sept 5-30 $25,000. Permit# 1108.

Experience the ultimate North Fork summer with the perfect combination of comfort and privacy in this spacious 4 bedroom home with heated pool on 3.5 acres. Explore the pristine beaches, beautiful vineyards and breweries or check out one of the many chef renowned restaurants the area has to offer. This property is the ideal retreat for a memorable summer getaway on the North Fork.

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.