$33,000
$33,000
Available: Right Now
Listed: 15/04/2024
37 Gardiners Bay Drive, Shelter Island Heights, Suffolk County, NY 11964, USA
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...
$10,770
Available: Right Now
Listed: 16/04/2024
Town of Southold, NY, 11944
The 19th-century historic and centrally located Stirling Square in Greenport Village has been reimagined into the modern and tasteful American Beech Boutique Hotel, Restaurant & Bar. During your stay, you can explore the vibrant village, natural scen...
$36,750
Available: Right Now
Listed: 16/04/2024
Shelter Island Heights, NY
This is a 2 house property that can sleep up to 15 if necessary. The Main house has 4 bedrooms and 3 baths, while the cottage has 3 bedrooms and one bath -- as well as an outdoor shower! You can rent one or both--it is up to you! The homes sit on a l...
$22,710
Available: Right Now
Listed: 16/04/2024
Town of Shelter Island, NY, 11964
* Please Read House Rules And Policy's Before Booking*Perfect For Families!! New to the rental market in 2022! Located within close proximity to Sandy beach with sunsets galore and resort areas, this neat-as-a-pin home has all the ingredients for...
$23,220
Available: Right Now
Listed: 19/04/2024
Town of Southold, NY, 11944
Newly renovated modern farmhouse with the perfect blend of style & comfort. Bask in the serenity of our fully equipped 600 sq ft deck and outdoor oasis (includes plenty of comfy seating, dining, Weber Genesis II grill, fire pit table, and so much mor...
$22,000
Available: Right Now
Listed: 15/04/2024
130 Johnson Place, Village of Greenport, Southold, NY 11944, USA
Greenport village 5 bedrooms, 2 baths with sweeping Water Views, adjacent to 6th St bay beach and park. Architect-designed and decorated interiors, chef's kitchen, 2nd floor sundeck and large yard with garden and outdoor dining area. Huge water-facin...
$21,750
Available: Right Now
Listed: 19/04/2024
Town of Southold, NY, 11944
This condo is one of the nicest decorated in Cliffside. Gorgeous shiplap walls with navy accents. It has a beautiful fireplace, new deck and much more. This unit has the capabilities to be handicap accessible. The master bathroom has a queen size bed...
$20,000
Available: Right Now
Listed: 15/04/2024
2 Hagar Road, Shelter Island, Suffolk County, NY 11964, USA
Available short term, this 4 Bedroom waterfront house creates incredible freedom between the insides and outside living areas. The expansive covered porch overlooking the water is a tranquil place to relax and entertain. The pool area is a special ha...
$40,500
Available: Right Now
Listed: 16/04/2024
Town of Shelter Island, NY, 11964
Bright and beautiful, this home promises tranquility. Wake up to a glistening pool outside your bedroom door with distant water views to the Peconic Bay. Walk to beach in private beach community. Take the kayak or paddle board out to connect with the...
$15,330
Available: Right Now
Listed: 17/04/2024
Town of Southold, NY, 11944
Welcome to our most lovely Greenport Beach Home.....800feet to sixth street beach and playground. A true beach getaway, with beautiful outdoor patio, outdoor shower, covered front porch and covered balcony off the master bedroom. Spacious private yar...
$85,000
Available: Right Now
Listed: 15/04/2024
23 West Neck Road, Shelter Island, Suffolk County, NY 11964, USA
Rental Registration #20L-0086This farmhouse features a wrap around porch, free form pool and large lawn and open floor plan. With an open layout, entertaining guests is easy. The kitchen features granite countertops, stainless steel appliances and br...
$26,160
Available: Right Now
Listed: 17/04/2024
Town of Southold, NY, 11944
High on a bluff overlooking the Sound, this amazing Sound front home has been completely renovated with a chef's gourmet kitchen (fully equipped), bright open living room, panoramic water views from every room. 3 Bedrooms, 2 bathrooms and a huge deck...
$11,280
Available: Right Now
Listed: 17/04/2024
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...
$20,000
Available: Right Now
Listed: 15/04/2024
42 Jaspa Road, Shelter Island, Suffolk County, NY 11964, USA
This pristine, recently renovated five bedroom Cape Cod is ready for summer! Conveniently located within close proximity to beach, fine dining, recreation areas, and bordering a preserve. Two story home with chef's kitchen, high end appliances, quart...
$23,970
Available: Right Now
Listed: 18/04/2024
Town of Southold, NY, 11944
Please read full description ! Rental registry # 0952Private modern cabin near the bay situated on 3.8 acres on culdesac. The cabin is set 200 ft off a quiet culdesac that lies across the street from Gull Pond. Separated on three sides by ...
$62,500
Available: Right Now
Listed: 15/04/2024
8 Chequit Avenue, Shelter Island Heights, Suffolk County, NY 11965, USA
Paradise Found. A waterfront splendor. Where modern meets magical. Stepping into this modern barn style home begins an experience of inspiration. Surrounded by water and actually built over water, this 3 bedroom retreat is an architectural treat. Mas...
$5,970
Available: Right Now
Listed: 16/04/2024
Town of Southold, NY, 11944
The 19th-century historic and centrally located Stirling Square in Greenport Village has been reimagined into the modern and tasteful American Beech Boutique Hotel, Restaurant & Bar. During your stay, you can explore the vibrant village, natural scen...
$40,000
Available: Right Now
Listed: 15/04/2024
37 Grand Avenue, Shelter Island Heights, Suffolk County, NY 11965, USA
Rental Registration #2022-S-0002.Since the turn of the century, this Victorian has greeted visitors coming from the North Ferry onto Shelter Island. It has a new life with a full-scale, high end restoration that imbues the best of yesterday with the ...
$25,110
Available: Right Now
Listed: 19/04/2024
Town of Shelter Island, NY, 11964
Feel like you are on a luxury cruise ship! Beautiful Shelter Island three bedroom/ three bathroom home. Large living room/dining room, two car garage. The home has unobstructed expansive views of Peconic Bay. This bright and airy house faces ...
$72,000
$72,000
Available: Right Now
Listed: 15/04/2024
15 Stearns Point Road, Shelter Island Heights, Suffolk County, NY 11965, USA
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 ...
$21,990
Available: Right Now
Listed: 16/04/2024
Shelter Island, NY
Steps from the beach, this beach house is the perfect destination to enjoy beautiful Shelter Island. Recently renovated summer home across a private beach with large windows, and a sizable garden. The property is two-story with five bedrooms, three b...
$34,000
Available: Right Now
Listed: 15/04/2024
60 Midway Road, Shelter Island, Suffolk County, NY 11964, USA
Shelter Island waterfront 4 bedroom, 3.5 bath contemporary with extraordinary views toward West Neck Harbor. Located on a landscaped acre on a lovely, peaceful inlet, this two story home enjoys beautiful views from the main floor living room with fir...