$22,050
Available: Right Now
Listed: 28/06/2024
Town of Shelter Island, NY, 11964
A water front home with magnificent Shelter Island Sound views from the entire main area, including living room, porch, pool and other areas of the home; this house is your vacation paradise. It has four bedrooms (comfortably sleeping 8), as well as ...
$24,750
Available: Right Now
Listed: 28/06/2024
Town of Shelter Island, NY, 11964
Summer 2023 calendar has been updated ! The month of July is now available and can be rented for the entire period or in 2 week blocks- August 1-18 is also available Please note 2 week minimum rental period This serene, modern sun drenched spacio...
$35,730
Available: Right Now
Listed: 24/06/2024
Town of Southold, NY, 11944
Snug Harbor StylishPristine waterfront home with direct access to private bay and dock, primary bedroom balcony, spacious deck with grill, multiple outdoor lounge areas, minutes to Greenport village and local beaches!3BR/4BA:Nautical-themed i...
$18,000
Available: Right Now
Listed: 28/06/2024
Town of Shelter Island, NY, 11964
This family friendly private three-bedroom, two bathroom Silver Beach ranch house is perfect for any season. Enjoy the pool, covered porch and walking distance to beaches and bays, the large chef's kitchen and comfy living room with fireplace in cool...
$37,500
Available: Right Now
Listed: 28/06/2024
Town of Shelter Island, NY, 11964
4 sunlit bedrooms (two with private bath), two story living room with open floorplan, extra sleeping space, gas fireplace, extended wifi, smart TVs, large decks with lots of outdoor seating and heated in-ground pool. Lovely private landscaped grounds...
$70,470
Available: Right Now
Listed: 23/06/2024
Town of Shelter Island, NY, 11964
Take the singular Shelter Island drive over Ram Island’s renowned causeways to this meticulously renovated and expanded 1933 charming, waterview home of stone and cedar on the most sought after Big Ram Island block. 5 bedrooms, 6 bathrooms and large ...
$36,540
Available: Right Now
Listed: 23/06/2024
Shelter Island Heights, NY
Beautiful turn-of-the century Victorian Summer Beautiful turn of the century home located on Rainbow Park with breathtaking views of Dering Harbor !Large sunny eat- in kitchen with marble floors and countertops with access to veranda and patio to...
$25,500
Available: Right Now
Listed: 24/06/2024
Town of Shelter Island, NY, 11964
*** 2024 update please read *** We are offering : Monthly or md-ld only . Prices are listed as monthly rates for the periods above .Lush, private 2 acres with heated gunite pool and gorgeous views of the ...
$19,530
Available: Right Now
Listed: 28/06/2024
Town of Shelter Island, NY, 11964
Please note that a reservation for this property needs to be approved before it is confirmed.Shelter Island Modern RanchBeautiful Ranch Style Shelter Island Home with Private Pool, Close to Golf Courses, The Beach, Art Galleries3BR/2.5BA:...
$25,860
Available: Right Now
Listed: 24/06/2024
Shelter Island, NY
Relaxation begins on the 6 minute ferry ride to this magical island. Summerfield is a spectacular, grand compound that has it all. Huge main house great for groups, 4700ft w/ privacy for all overlooking serene nature reserve. Star gaze in the bubblin...
$11,280
Available: Right Now
Listed: 25/06/2024
Town of Southold, NY, 11944
Modern on 9th Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Originally an old-time candy and soda shop this 1957 home is truly a charmer. Recently updat...
$18,000
Available: Right Now
Listed: 28/06/2024
Town of Southold, NY, 11944
Beautiful updated historic home in the village of Greenport. Central AC, newly renovated kitchens and bathrooms, large fenced in yard, patio with bbq, outdoor shower, fire pit. Bike to nearby vineyards and beaches and walk to restaurants, stores and ...
$12,000
Available: Right Now
Listed: 23/06/2024
Shelter Island, NY
Sleeps 4 adults (max) or total of 6 with kids.Perfect family getaway.Shelter Island Rental License #: 2023-V-0018Weekly and Monthly Discounts for Winter Rentals!Stay at our newly renovated, light filled home! In the warmer months loun...
$30,000
Available: Right Now
Listed: 24/06/2024
Town of Southold, NY, 11944
Welcome to this stunning & newly renovated Greenport home. This magnificent home seamlessly blends comfort, style and luxury living. The home provides a bright & airy feel throughout amongst its two levels of living. The first floor provides two spac...
$30,840
Available: Right Now
Listed: 25/06/2024
Town of Shelter Island, NY, 11964
If you’re looking to escape bustling city life, book this 5-bedroom, 6.5-bath home in the Hamptons area! This Shelter Island vacation rental features an office and free WiFi, as well as amenities like a game room and pool to ensure a productive and r...
$32,010
Available: Right Now
Listed: 28/06/2024
Town of Southold, NY, 11944
The perfect getaway. Within walking distance to beach, town, Jitney, LIRR and ferries to the South Fork. This quiet and bright house is located in the heart of Greenport. Enjoy wineries, breweries, amazing restaurants, shops and beaches.Guests ha...
$39,990
Available: Right Now
Listed: 28/06/2024
Town of Southold, NY, 11944
Same location I have two 2 cottages that sleep 4 each . See VRBO search bar [Where To] with the ListingID 173361and the ListingID 167288.The centerpiece of this family owned waterfront estate, “The Main House” is a neo-victorian 5-bedroom, 3-bath...
$14,130
Available: Right Now
Listed: 25/06/2024
Town of Shelter Island, NY, 11964
Great house in great location. 3 bedrooms (including one with bunk bed and additional bed) . Open floor plan with updated kitchen and bathrooms. In addition to large pool, great yard and outdoor shower. Short walk to nearby beach or bike to Sunset or...
$84,000
Available: Right Now
Listed: 28/06/2024
Town of Shelter Island, NY, 11964
This luxury home includes 6 bedrooms with additional sleeping accomodations for 4 in the downstairs walkout recreational room. All bedrooms have ensuite baths, 300 count linens & mutiple pillows & plush towels. The gourmet kitchen is a cook's dream. ...
$49,800
Available: Right Now
Listed: 28/06/2024
Town of Shelter Island, NY, 11964
Wake up smiling every morning in this sun-filled house. Spend days lounging and evenings grilling and dining around the 40 long pool. Relax inside on the comfortable museum quality modern furniture or warm yourself by the hanging, rotating fireplace....
$33,870
Available: Right Now
Listed: 23/06/2024
Town of Shelter Island, NY, 11964
This Shelter Island beach house has all the necessary ingredients for a fabulous year-round getaway. Located on a shy acre just outside the Village of Dering Harbor, this sun-filled and spacious waterfront home is on a slight elevation, with 150-foot...
$72,720
Available: Right Now
Listed: 28/06/2024
Shelter Island, NY
Sunset BeachElevated Views Over Shelter Island Sound, Wraparound Deck Overlooking Beach, High-End Amenities, Access to sandy dock6BR/5.5BA,Cinematic Media Room, Fitness Room, 2 Docks, Indoor Pool & SpaTheres ordinary, and theres Sunset Be...