$60,000 per month
16 Little Ram Island Dr, Shelter Island, NY 11964
In one of the most sought after locations on Shelter Island, this original waterfront cottage has the most beautiful water views overlooking Coecles harbor to Gardiners Bay, with full sunlight from Sunrise to Sunset. This 4 bedroom 2 bath property sits at the end of a long winding driveway providing great privacy. There has been a new kitchen renovation now providing water views while cooking.
$50,000 per month
28 Gardiners Bay Dr, Shelter Island Heights, NY 11965
Experience the ultimate in tranquility and luxury at this secluded oasis, where every moment is a picturesque escape. Discover breathtaking panoramic water views and soak in the mesmerizing sunrise & sunsets over Gardiner's Bay from just about every room in the house. Boasting an impressive layout featuring an open plan den/media room, dining room, and chef's kitchen-all thoughtfully designed to
Michael Brennan Douglas Elliman Real Estate
$50,000 per month
37 Tuthill Dr, Shelter Island, NY 11964
WHEN AN ARTIST MAKES A HOME Serena Dugan, Co-Founder of Serena&Lily has completed her renovation of 37 Tuthill Drive, Shelter Island. This property is a robust representation of Serena's vision as an artist and a designer. Each detail was carefully considered and selected, and her point of view is visible throughout the house. The artwork, fabrics, and wallpapers are of her design. In some
$18,000 per month
5 Bay Ave, Shelter Island, NY 11964
Open plan beach house with superb water views located in the highly sought after Montclair Colony. Centrally located near markets and many conveniences, there is much to adore in this home. Open plan living room with sunroom, dining and eat in kitchen. This home offers two bedrooms with two full baths and another bedroom with a full bath over the two car garage. In addition the master bedroom has
Michael Brennan Douglas Elliman Real Estate
$26,450 per month
13 Brander Pkwy Unit ID1014115P, Shelter Island, NY 11964
Welcome to Sandpoint, an exclusive Shelter Island retreat nestled on 1.4 acres, just a stone's throw from a sandy beach and across from a 12-acre preserve. This stunning home features five bedrooms, including two master suites and one room with twin beds. Sunlit and spacious, the heart of the home is a well-equipped kitchen with an oversized island overlooking a large pool and landscaped grounds.
$75,000 per month
15 Montclair Ave, Shelter Island, NY 11964
Enjoy all The Hamptons have to offer in this newly recreated waterfront home in the heart of West Neck Harbor! Complete with a boat and complimentary captain at the end of your private dock. Every detail was masterfully thought through by a leading design team. The floor plan offers a first-floor primary suite, four additional private guest bedrooms with two gracious common living spaces, a
Margot Reutter Corcoran
$40,000 per month
6 Cobbetts Ln, Shelter Island, NY 11964
An incredible property with everything you need for a fantastic summer vacation. This 5-6 bedroom, 5 bath home features a spacious, open living room with fireplace, dining area, charming eat-in country kitchen, media room, waterview deck, wrap brick patio, heated pool, tennis court and small strip of beach! All on 3 acres with stunning waterviews. Available for winter rental. [[Rental
$50,000 per month
21 Peconic Ave, Shelter Island, NY 11964
Impeccable cottage ideally located in the heart of Silver Beach. Very Closeto the secluded association beach and a short distance to Shell Beach. Lovely deck with water view and cool summer breezes. Three bedrooms and two bath. Ref. R103 MD - LD $50,000 June - LD $50,000, June $10,000, July $20,000, and August $25,000
Melina Wein M WEIN REALTY INC
$25,000 per month
21 Peconic Ave, Shelter Island, NY 11964
Discover summer on Shelter Island in this newly renovated and beautifully furnished 3 bedroom two bath cottage , with wrap around decks overlooking Peconic Bay and evening Sunsets. Located in this quiet community with Beaches directly across from your house this is Summer as you remember it. The open floor plan of the house provides great spaces for family and friends to enjoy meals and gather
$38,500 per month
91 Shore Rd, Shelter Island, NY 11964
A romantic and secluded summer getaway. Enjoy a front row seat to breathtaking and dramatic views of the Shelter Island Sound, Crescent (Sunset) Beach, Quinipet Sailing, North Ferry, Greenport, Southold and 4th of July fireworks. Conveniently just steps from Kissing Rock, Crescent Beach, The Pridwin Hotel (Spa and Restaurant), Sunset Beach (Restaurant and Nightlife), Shelter Island House
$35,000 per month
6 South St, Shelter Island Heights, NY 11965
Charm, history, location. Built as a carriage house circa 1890, this little gem has been meticulously restored and decorated. First time offered as a rental since it's restoration was completed in 2021.This is a chance to live and enjoy a part of Shelter Island history. bounded on two sides by preserved land and an estuary, the woodland setting provides year-round beauty and tranquility in the
$17,000 per month
6 Crab Creek Rd, Shelter Island, NY 11964
It all about the sandy Peconic Bay beach and stunning maze of creeks at the end of this quiet street. Create wonderful summer memories in this open and comfortable cottage. After a fun day at the waters edge unwind in the bright and airy sun-room with easy access to large deck and peaceful yard. Living room with high ceiling, skylights and fireplace flows into dining room and kitchen providing
$24,000 per month
9 Country Club Dr, Shelter Island, NY 11964
This open and bright 3 bedroom 2 Bath with heated pool is the perfect summer escape. Enjoy strolls on beautifully preserved Menhaden Beach from this quiet enclave. The house features central air, outdoor shower, finished lower level, comfortable outdoor areas with decks and patios, Pet considered [[Rental Registration # 2023-L-205]]
$31,000 per month
17 Stearns Point Rd, Shelter Island, NY 11964
Located within close proximity to popular Sunset Beach, golf, tennis and Perlman Music Camp in desirable resort area, this hand-crafted Scandinavian style farmhouse with summer guest cottage and barn with loft on 1.5 acres was thoughtfully built and completed in 2010 using rich textures and environmentally efficient amenities. Pine and cedar aromas fill the air inside this beautifully sunlit
$45,000 per month
34 Country Club Dr, Shelter Island, NY 11964
Located on the Gardiners Bay Country Club, this gorgeous newly built home features an open living room, dining room and wonderful high end kitchen. Bedrooms feature en-suite baths and are all tastefully decorated. This open layout is wonderful for entertaining, from the kitchen to the covered porches overlooking the heated pool and GBCC beyond. For further enjoyment, there is a pickleball
$30,000 per month
28 Cobbetts Ln, Shelter Island, NY 11964
Secluded 3+ bedroom, 2.5 bath contemporary on 1.5 beautiful acres with new gunite, heated pool. Common rooms include open plan living room with soaring ceilings and fireplace, comfortable dining area and kitchen with new appliances. The primary bedroom suite has a king bed and full private bath. All overlook a back expanse with deck, fenced pool and gorgeous trees. A tv media room is also on
$55,000 per month
4 Bay Ave, Shelter Island, NY 11964
This clean and modern harborfront home is located in an area that features glorious sunsets. There are lovely gardens and shade trees with meditation areas to read or relax in, and the main home offers an open floor plan, with an L-shaped living room that maximizes views of the water, a fireplace for chilly nights, dining area overlooking the water, and efficient kitchen. There is a first floor
$26,000 per month
71 Gardiners Bay Dr, Shelter Island, NY 11964
Beautiful home across the street from beach access, relax and unwind in this 4 bedroom 3 bath home steps to beach. Back deck off the dining room for additional entertaining space. Additional playroom on the lower level. The kitchen and baths are recently updated. [[Rental Registration # 2025-V0002]]
$15,000 per month
10 Crescent Way, Shelter Island, NY 11964
This 4 bedroom 3 and a half bathroom awaits your summer vacation. Perfect for families, entertaining, and relaxing. The first floor features 3 bedrooms including a guest suite. Additional 2 bedrooms with a shared bath and a half bath. The eat in kitchen, living room with cathedral ceilings and dining room blend for seamless entertaining. The second floor features a private primary ensuite
$90,000 per month
15 Montclair Ave, Shelter Island, NY 11964
Enjoy all The Hamptons have to offer in this newly recreated waterfront home in the heart of West Neck Harbor! Complete with a boat and complimentary captain at the end of your private dock. Every detail was masterfully thought through by a leading design team. The floor plan offers a first-floor primary suite, four additional private guest bedrooms with two gracious common living spaces, a
$39,000 per month
37 Gardiners Bay Dr, Shelter Island, NY 11964
Within close proximity to sandy Hay Beach, this immaculate 4 bedroom, 4 bath cedar shingled three-level modern has the spirit of living in a birds nest with sliding glass doors and porches everywhere overlooking cherry trees and wrap around deck, bay breezes blow throughout gently. The kitchen is a chef's delight, with granite counters, maple cabinets, Viking stove, Monogram refrigerator, Bosch
$69,000 per month
32 Hilo Dr, Shelter Island, NY 11964
This wonderful traditional has been totally remodeled and is a wonderful August rental. Four bedrooms, 3 with the most beautiful water views, and 4 and a half remodeled baths as well as a remodeled kitchen is the type of summer rental one is always dreaming of. Located on a water front bluff in Hilo Shores, sip cocktails on the veranda overlooking the pool and West Neck Bay in the distance. If
$35,000 per month
50 Country Club Dr, Shelter Island, NY 11964
Sited on a gentle rise, minutes from Menhaden Lane beach, the stunning, Philip Johnson's Glass House inspired restoration of this Mid Century Modern home, has brick flooring throughout the main floor and an abundance of natural light. The home has splendor with the added benefits and comforts of today's amenities. Three bed three bath, with the den converting into the fourth bedroom/ private
$50,000 per month
151 N Ferry Rd, Shelter Island, NY 11964
This stunning 5 bedroom, 4.5 bath home has 6 acres and easy access to Dering Harbor Marina, the Shelter Island Yacht Club, Town dock, ferry, tennis, shops and restaurants in picturesque Shelter Island Heights. The house has first and second floor verandas, a center hall foyer, flanked by the living and dining rooms with a family-room, fireplace, powder room, marble and stainless kitchen and mud
$18,000 per month
6 Summerfield Place, Shelter Island, NY 11964
Charming Summer Victorian on Water. The peaceful living room and dining room are surrounded by the stunning waterfront porch The open and comfortable eat-in-kitchen and family room are comfortable essentials to this easy living home. First floor bedroom with full bath along with five craftsman's bedrooms and waterfront screened in porch on the second floor completes this charmer! Near
$15,000 per month
3 Crab Creek Rd, Shelter Island, NY 11964
Prime Location is Silver Beach, 3 bedroom 3 bath home situated on 1.27 acres with heated gunite pool with bluestone patio and outdoor shower and Tennis/ pickleball court. There is a pool house with a half bath features a lounge area and a gym. Recently renovated and turn key.Located a short distance to Silver Beach Association beach. [[Rental Registration # 2024-L-0052]]
$25,000 per month
14 Montclair Ave, Shelter Island, NY 11964
Located in Montclair Colony on the southwest corner bring your boat to your own private dock. Watch the sailboats go by and enjoy fantastic sunsets. [[Rental Registration # 2025-L-0013]]
$25,000 per month
14 Great Cir Dr, Shelter Island, NY 11964
Recently updated with new bathrooms, kitchen and appliances, this wonderful Hay Beach house is located in a quiet neighborhood. Set on 1.20 Acres, the pool is private and inviting. Large patio and decks are at hand for wonderful summertime bar-b-ques. This is a wonderful summer rental with beaches nearby. [[Rental Registration # 2024-L-0007]]
$7,000 per month
17 Wade Rd, Shelter Island, NY 11964
Located near Coecles Harbor and Sylvester Manor farm, this 3 bedroom 3 bath ranch home has 2 newly updated bathrooms and central air conditioning. A great place to spend your summer days. [[Rental Registration # 2024-L-0037]]
$65,000 per month
2 E Brander Pkwy, Shelter Island, NY 11964
2023-L-0167 Shelter Island Silver Beach waterfront home. Stunning views surround this 3-4 bedroom, 3 bath home with deep water dock boat slip and waterside deck. Home has central air and gourmet kitchen. Close to town beach. [[Rental Registration # 2023-L-0167]]
$26,500 per month
185 N Ram Island Dr, Shelter Island, NY 11964
Set on 1.8 acres of bay front on Ram Island. House has 4 bedrooms, 2 bathrooms, sleek modern beach cottage decor, and has forever views onto Gardiner's Bay. The property is set up for gracious outdoor summer living, including a wall of sliding doors from living room, formal dining room and master suite overlooking the bluff, kitchen with granite countertops, vaulted ceiling, fireplace, infinity
$15,000 per month
11 Tims Trail, Shelter Island, NY 11964
Bright and Fresh 3 bedroom 2 bath ranch located on quiet street close to beaches. The open floor plan of the kitchen, dining room and living room creates a comfortable and relaxing space. The family room leads to outside dining, patio area and private yard. A nice place to enjoy this summer. [[Rental Registration # 2023L0141]]
$20,000 per month
8 E Brander Pkwy, Shelter Island, NY 11964
Stay two weeks in this charming four bedroom, two bath home features a living room with fireplace, den, country kitchen and large screened rocking chair porch with water view. Wake up early to explore the creek at sunrise or gather the gang for a splendid sunset walk. A special Silver Beach location. [[Rental Registration # 2024-S-0158]]
$37,000 per month
3 Primrose Place, Shelter Island, NY 11964
Located near Coecles Harbor, Gardiners Bay Country Club golf course, and several island beaches, this new home on a wooded acre enjoys a spacious open design with vaulted ceilings. Featuring a living room with a stone fireplace, dining area, stylish chef's kitchen with textured granite counters, breakfast bar, stainless appliances, a computer station, and breakfast nook overlooking a spacious
$50,000 per month
165 N Ferry Rd, Shelter Island Heights, NY 11965
This wonderful cottage is located next to town and everything one would need for a true summer rental. No car needed when arriving via the LIRR or Jitney which are both just a quick jaunt from this houses location. Ferry, restaurants, shops and galleries are all within proximity. With 3 bedrooms and 2.5 baths, this lovely cottage features an open floor plan, office, finished lower level with
$35,000 per month
9 Montclair Ave, Shelter Island, NY 11964
Built in 1929, this spectacular water front home on West Neck Bay is enjoyed from this 3-bedroom/ 3 bathroom CAC sunny home. Spacious rooms, a studio cottage with half bath and a dock with deepwater mooring complete the picture for the summer season. RR# 2021-L-0158 [[Rental Registration # 2024-L-0004]]
$40,000 per month
152 N Ferry Rd, Shelter Island Heights, NY 11965
This beautifully designed and furnished 3 bedroom home is the perfect Summer rental, central to all that you want on the Island , Ferry, Restaurants, Markets, and Beaches . Completely redesigned and constructed by Scott Murphy of Dirt Design/Build in 2020,this home features the highest quality finishes and fixtures. The large Kitchen is perfect for wonderful meal prep for friends and family
$100,000 per month
23 Tuthill Dr, Shelter Island, NY 11964
This newly updated ranch house on Tuthill Drive (a private road on Big Ram Island) has been reimagined with the greatest attention to detail and quality. The open plan connects a spacious sun and (high fidelity) TV room with living room (and wet bar),cook's kitchen, and full dining room Three bedrooms include a private guest suite (with steam shower)primary and secondary bedrooms both
$55,000 per month
5 Penny's Path, Shelter Island, NY 11964
This charming 3 bedroom house with a pool is comfortable, fresh and bright. The updated kitchen features stone counters, new stainless appliances, and practical counter seating. Great area for relaxing and entertaining in living room, dining room, and sunroom. A large deck surrounds the pool creating an easy flow for outside living and dining. . The house is located on a quiet street close by
$23,000 per month
4 Sheep Pasture Ln, Shelter Island, NY 11964
This beautiful Contemporary home has 1.8 acres of rolling green lawn and water views of both Coecles Harbor and Gardiner's Bay. The main floor has a great room with fireplace, vaulted ceilings, dining area and two-story windows that maximize the view. There is a wrap deck easily accessed from the living areas where there is a new gas grill and heat lamp for cooler summer evenings. The kitchen has
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