ML# :3452918   Classic North Fork Beach home located just 10 homes away from South Harbor Beach and Park, Amazing comfort and privacy on this acre plus setting. Home is crisp, clean, and fully furnished ready for you to enjoy. South Harbors expansive beach offers an inlet to paddle board, kayak, fish, and relax on the water. Please call for availability; 2024 Rates: May $5000, June $7000, July $8000, September $4500, October $4500, November $3500, December $3500 Southold Town Rental Permit #0374

ML# :3537205   Treasure the memories made during the Summer of ’24 at this chic waterview home overlooking Corey Creek. Completely redesigned and renovated in 2017-2018, this four bedroom, four bath (plus outdoor shower) open floor plan post-Modern boasts nearly every amenity. Located off the beaten path in quiet Laughing Waters, this home includes beach rights at the community’s private beach. Listed price is per week. Southold Town requires a minimum occupancy of two weeks. Permit # 0971.

ML# :3455253   NEW LOWER RATES FOR 2024! Make meaningful memories in this soaring contemporary overlooking beautiful Hog Neck Bay and Corey Creek. Enjoy water views from nearly every room. Open floor living/dining area. CAC, W/D, Internet/WiFi, all utilities included. Large waterside deck, huge patio with nearly-new Weber gas grill, outdoor shower, private community beach. Permit #0520

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.

ML# :3469228   Beautiful Harbor Lights Beach House available October 1st, 2023 - April 30th, 2024 for off season. Great location just 5 homes away from Harbor Lights Association Beach and Park and 1/2 mile away from Goose Creek Beach. This spacious ranch renovated in 2021 offers a comfortable open floor plan with cathedral ceilings. Bedroom suite includes a full bathroom. There are two additional bedrooms and a second full bathroom. Full fenced back yard surrounds the sun filled paver patio - lawn care included! Come enjoy this exquisitely updated home in a wonderful beach community! Southold Town Rental Permit #0471

ML# :3538553   In The Heart Of Downtown Southold, Close To Everything Including Einstein Square, Southold General, Maroni’s, Food Market, & All Downtown Shopping. Spacious Apartment Features 3/4 Bedrooms, and 2 Baths, Wood Floors.

ML# :3518830   This beautifully furnished farmhouse offers you a warm welcome home on the North Fork. Amazing decor throughout every room for you to enjoy your stay. There are three bedrooms and two full bathrooms, hardwood floors, central air conditioning, and a back deck overlooking a fenced in yard. Great location just one block from the town restaurants, shops, and all transportation. Numerous beaches to explore and make memories forever! Available November 1st -April 30th @ $3300 per month, May $5000, June $6000, August $10, 000, September $6, 000, October $5, 000. Two week stays are welcome! Southold Town Rental Permit #0898

ML# :3433327   The perfect summer spot ! Plenty of room in this beautiful home and enjoy the Reydon Shores private beach too! This comfortable home features a spacious kitchen which leads out into a grand deck for outdoor dining. There are 4 bedrooms and 3 bathrooms which includes a first floor master bedroom en-suite, living/dining room and a large family room. The amenities continue outside on the park-like backyard setting with an outdoor shower, basketball hoop, badminton and ping pong. The home is located just 9 homes away from the beach - 2 kayaks included. Available starting Sept $7, 000 off season months $3300. Southold Town Rental Permit #0641

ML# :3521304   The ’Yellow House’ sits on 5 secluded acres with beautiful vineyard views and sunsets. A large and sandy bay beach is located at the end of the road. The house is newly painted and furnished, has central air conditioning, oil heat, and newer kitchen appliances. A full-size washer and dryer are in the basement. The house has three bedrooms, two with queens and one with a twin. There is one full bath, a large upstairs office, a detached two-car garage, and a small patio in the back that overlooks the vineyard’s fields. Renters insurance and references required.

ML# :3528113   Founders Village 55+ community - one of the most sought after condo communities in Village of Southold. Great location in the condo complex with more grounds and open space. 2 bedrooms, 2 baths, fireplace in living room, washer/dryer on first floor. Plenty of storage space in the basement. Easy walk to town, shopping and public transportation. Pool and Club House. Walk to summer concerts on the Square on Main Street, library, grocery, and lots of restaurants, shops, post office, and public transportation close by - every thing you need!