ML# :3552206 Not available for year round rent at this time. Newly renovated three bedroom, two bath bungalow just outside of popular Greenport Village.This house provides a sense of privacy and relaxation close to the beach. Located less than one mile away, the captivating Rocky Point Beach is a picturesque retreat for everyone to enjoy. Additionally, there is the exquisite Truman’s Beach nearby, which provides a stunning view of Connecticut. Lavender Bay and Sep’s Farm are conveniently located only 0.4 miles away.The exterior of the property is designed for entertainment, featuring a spacious patio, barbecue area, fire pit, and even an outdoor shower to refresh after a dip in the nearby beaches.
1850 Rocky Point Rd, East Marion, NY, 11939
ML# :3482797 This Luxury Beach Cottage is an adorable and affordable getaway located directly on the beach and is 5 min from the long stretch of vineyards and farm stands. Enjoy kayaks, stand-up paddle boards, and floats. Everything you would possibly need for a wonderful stay at the beach. The home’s large patio doors open onto the warm sand, with lounge chairs, outdoor dining, a gas grill, an outdoor hot and cold shower, and non-motorized water toys ready for you to enjoy. We are pet-friendly here on the beach so bring your furry friend’s leash and get ready for some nice, long walks on the beach. This is a 1-bedroom home that has a queen bed, a sofa bed, and a full bathroom, that sleeps 4 people. You also have access to the boat or vehicle parking. You are free to explore local destinations including the vineyards for wine tasting, farm stands to support local growers, a close-knit beach community, and nature reserves to explore. A 5-star restaurant is just across the street and 5 minutes away as well as the Hamptons, Greenport, Montauk, and/or Shelter Island.
2 Oak Street, Wading River, NY, 11792
ML# :3541214 Newly renovated farmhouse located in the heart of Greenport village. This 3 bedroom 2 bath first floor apartment is steps to shops, restaurants & historic waterfront. Enjoy summer days in the potager garden and nights grilling the daily catch. The apt features a sunny open kitchen with an open floor plan, a master bedroom with en suite bath, and two additional bedrooms with ample light and a cozy feel.
412 Carpenter, Greenport, NY, 11944
ML# :3549344 Welcome to Greenport waterfront! This charming two bedroom, two bathroom furnished vacation rental has everything you need to unwind and relax. This home boasts a great flow for entertaining for the ultimate getaway. A community pool, private beach, dock, tennis and a stone’s throw to town complete the package. Laundry in unit. Prime waterfront location with stunning views from the patio are enviable in any weather. This unit is crisp and clean. Just a few feet from the sandy beach and pool & tennis courts. Close to easy day trips on the ferries to Shelter Island and the Hamptons and near to Long island’s famous North Fork Wine Trail.
35 Stirling Cove, Greenport, NY, 11944
ML# :3547655 Situated in a charming and serene neighborhood in Greenport and located just minutes from both Greenport Village and Southold Town Beach, this recently updated Cape offers 1, 500 sq. ft. with 4-bedrooms, 2-baths and a spacious living area that flows seamlessly into a bright and airy eat-in kitchen. A full, unfinished basement leads out to an expansive, fenced backyard, and the attached 1-car garage and driveway capable of accommodating 2 additional vehicles ensures sufficient parking for tenants. Don’t overlook the opportunity to rent this gem! Please note that the reported square footage is an approximation as the Town of Southold does not have records of the square footage for the second half story.
27 Madison Street, Greenport, NY, 11944
ML# :3529654 Summer in Orient. Relax on the front porch of this 3 bedroom, 2 bath Ranch in Green Acres, a short walk to association Sound beach & Orient State Park. Open floor plan with updated kitchen, wood burning fireplace & rear deck off dining area - perfect for entertaining. Private yard with specimen trees & vegetable garden with automatic sprinkler system. Available MD-LD $19, 000; June $4, 000; July $7, 000; August $8, 000; September $4, 000. Permit # 0208
80 Greenway West, Orient, NY, 11957
ML# :3515044 Beautiful and inviting are words that come to mind when describing this welcoming vacation home in the charming private beach community of Paradise Shores. Only 200’ to the community’s private beach, and picnic area, the home has water views, 5 bedrooms, 2 baths, a screened in porch for lazy days, an upstairs balcony to take in the view, a large outdoor shower w/changing room, an outdoor kitchen on the back deck for entertaining and a cozy firepit area. Central air and ceiling fans in each bedroom for comfort. All tastefully decorated with a relaxed vacation vibe. Oh, and Kayaks are available too! Every inch of this home feels like your dream vacation! (Southold Town Rental Permit #0984). 2024 Rates: June $16k or $4k/week, July $25k or $5k/wk, First 3 weeks in August $6k/week. September, after LD, $4, 500/week. Two week minimum applies to all stays.
2460 Paradise Shores Rd, Southold, NY, 11971
ML# :3489910 Cozy ranch home with a backyard overlooking a farm. Heated pool, completely updated furniture, paver patio, fire pit, and bbq. Amazing location with water access for small boats, kayaks, and paddle boards down the road. A beautiful sandy beach less than one mile from the home. Multiple beaches to enjoy! Many extraordinary vineyards less than a mile from the home. Available May - September at $9, 000 per month. Southold Town Rental Permit #0934
885 Little Neck Rd, Cutchogue, NY, 11935
ML# :3455258 Year Round ONLY $4500 Per Month!! Welcome To Plum Island Lane In The Much Sought After Community Of ’Orient By The Sea’ - Which Is A Stones Throw From The Private Beach! This Perfect Get Away Home Consists Of 3 Large Bedrooms, 1.5 Bathrooms, A Spacious EIK, Bright Open-Plan Living Room, Laundry And Recently Installed In-Ground 20 x 40 Saltwater Swimming Pool! This Gem Of A Home Was Completely Renovated To A Premium Standard In 2021. It Is Fully Furnished And Contains All New Modern Appliances. Close To The Cross Sound Ferry, Orient State Park And Public Marina. Reserve A Viewing Right Away And Avoid Missing Out On This Beauty! May: $6, 000 - June: $10, 000 - July: $18, 000 - August to LD: $18, 000 - September: $9, 000 & MD to LD: $32, 000. Rental Permit #: 0812
2420 Plum Island Lane, Orient, NY, 11957
ML# :3253024 Welcome to this Comfortable open-concept waterfront home, in private neighborhood views of Peconic Bay from house and deck. The home boasts 2 new decks, and a new master bath. Getaway yourself, or with friends and family. Four beds, 3 baths, with two queen beds, two full, and a King Master bedroom and new spa-like master bath-Jacuzzi bathtub, rain shower head to relax the days away. First-floor bedroom with attached bath. Private Bay Beach for the neighborhood. Natural Gas for BBQ, Great wrap-around deck to relax and dine by the water with an Outside gas fireplace to warm you. Cable/Streaming/Wi-Fi boost for working from home, CAC too. Additional living area in the basement. Relax by the outside firepit facing the water. Close to vineyards, breweries, restaurants, and shopping. Pets welcome. Available Sept-May.
61 Brookside, Jamesport, NY, 11947