$60,000
Available: Right Now
Listed: 03/05/2024
14 A Heron Lane, Shelter Island, Suffolk County, NY 11964, USA
Stylishly renovated beach house with spectacular sunrise to sunset water views on a sandy beach. Set on West Neck Harbor with 3 waterside ensuite bedrooms plus a study with convertible sofa and 4 bathrooms in all. In a lovely setting well off the mai...
$19,290
Available: Right Now
Listed: 04/05/2024
Town of Southold, NY, 11944
Long term stay available - please inquire* Entire house with pool * Fenced in yard *Located in Greenport, New York. This property offers a private pool, free WiFi and free private parking,...
$39,000
Available: Right Now
Listed: 03/05/2024
11 Tim's Trail, Shelter Island Heights, Suffolk County, NY 11964, USA
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 privat...
$13,740
Available: Right Now
Listed: 05/05/2024
Town of Southold, NY, 11944
Set in the historic section of Greenport village, the Captain’s House, built in 1820, is an elegant and charming 3 bedroom, 2 bath home ready to enjoy, especially for a summer getaway or a cozy holiday retreat. It's a 3 block walk into town and a sho...
$6,750
Available: Right Now
Listed: 01/05/2024
Shelter Island Heights, NY
Come stay in the heart of Shelter Island, central to all beaches, shopping, and restaurants. Spacious 3 bedroom ranch sleeps up to 6, with blissfully comfy "W Hotel" beds. Bedroom lamps have built-in USB ports for charging your phone. Living room wit...
$13,000
Available: Right Now
Listed: 03/05/2024
30 Brander Parkway, Shelter Island Heights, Suffolk County, NY 11964, USA
This charming farmhouse features 3 bedrooms, 3 full baths, open living, dining, and a kitchen with doors out to the large deck with a pool. Located in the Silver Beach area of Shelter Island, it is within close proximity of the most beautiful beaches...
$12,000
Available: Right Now
Listed: 30/04/2024
Town of Southold, NY, 11944
Discounts available for stays 14 days. Please inquire prior to booking for details.Completely updated, modern and light-filled Cape Cod-style home. You cannot beat this location overlooking the vineyard and only a short walk to the beach or a sho...
$47,000
Available: Right Now
Listed: 03/05/2024
14 Westview Road, Shelter Island Heights, Suffolk County, NY 11964, USA
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...
$95,000
$95,000
Available: Right Now
Listed: 03/05/2024
4 Sheep Pasture Lane, Shelter Island Heights, Suffolk County, NY 11964, USA
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...
$30,000
Available: Right Now
Listed: 03/05/2024
55 B North Cartwright Road, Shelter Island, Suffolk County, NY 11964, USA
Original Farmhouse in great location, offering complete privacy on 3.4 acres. Beautiful private large property overlooking nature preserve. First floor has a living room with fireplace, family/TV room with french doors opening up to the back gardens,...
$38,910
Available: Right Now
Listed: 06/05/2024
Shelter Island Heights, NY
This newly renovated sun-drenched Shelter Island retreat with an exquisite 21'x42' Gunite, wifi-enabled luxury heated pool is located in the tranquil Hay Beach area on a shy acre within close proximity to sandy beaches. A 1971-built ranch style charm...
$16,560
Available: Right Now
Listed: 02/05/2024
Town of Southold, NY, 11944
Cozy Greenport CottageOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Welcome to Maple Street Manor, managed by Vacasa. This house is located in Greenport...
$13,500
Available: Right Now
Listed: 01/05/2024
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...
$13,500
Available: Right Now
Listed: 04/05/2024
Town of Southold, NY, 11944
This beautiful house is located in a private beach community. An 8 minute walk brings you to a private beach with views of the Peconic Bay and Shelter Island. Enjoy the complimentary use of two kayaks and two stand up paddle boards, which are easily ...
$50,000
$50,000
Available: Right Now
Listed: 03/05/2024
4 B South Ram Island Drive, Shelter Island Heights, Suffolk County, NY 11965, USA
This post-modern summer rental has a large open kitchen, dining and living room with French doors leading out to a large deck with Gunite pool. Separate library with doors leading out to the screened in porch has wonderful sunset views. Two guest roo...
$85,000
Available: Right Now
Listed: 03/05/2024
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...
$35,000
Available: Right Now
Listed: 03/05/2024
318 Fifth Street, Village of Greenport, Southold, NY 11944, USA
Greenport Village West Dublin architectural home is available for you to enjoy! This wonderful home includes 3 bedrooms, 2 full baths, formal dining room, beautifully designed open floor with impeccable detail. The backyard setting is fabulous with p...
$60,000
$60,000
Available: Right Now
Listed: 03/05/2024
18 Little Ram Island Drive, Shelter Island Heights, Suffolk County, NY 11965, USA
In one of the most sought after locations on Shelter Island, this original waterfront cottage has the most beautiful waterviews overlooking Coecles harbor to Gardiners Bay, with full sunlight from Sunrise to Sunset. This 4 bedroom 2 bath property sit...
$25,000
Available: Right Now
Listed: 03/05/2024
116 South Ferry Road, Shelter Island, Suffolk County, NY 11964, USA
Comfortable, charming cottage with central air conditioning and expansive family room with iron day beds for relaxation post a day at the beach. Blue stone patio with Brown Jordan furnishings and outdoor shower. Home has three bedrooms and two baths ...
$22,000
Available: Right Now
Listed: 03/05/2024
412 Carpenter Street, Village of Greenport, Southold, NY 11944, USA
Newly renovated farmhouse located in the heart of Greenport village. This 3 bedroom 2 bath first floor apartment is steps to shops, restaurants and historic waterfront. Enjoy summer days in the potager garden and nights grilling the daily catch. The ...
$18,000
Available: Right Now
Listed: 04/05/2024
Town of Shelter Island, NY, 11964
This charming and newly renovated 3 bedroom, 2 bath ranch style home is located on a quiet street close to both Sunset and Shell beaches and within walking distance to Silver Beach off of Bootleggers Alley. We have bikes on hand to help you reach the...
$35,000
Available: Right Now
Listed: 01/05/2024
114 Wade's Beach, Shelter Island, Suffolk County, NY 11964, USA
This gleaming contemporary beach house is as stylish as they come. Completely renovated with new baths, kitchen, and lovely fresh and great looking furniture, this house is a pleasure to visit. There is a master suite plus two bedrooms, a dining room...