Southold NY Real Estate & Homes for Rent

Enjoy this Waterfront rental just steps to Goose Creek beach. Easy water access to Goose Creek from this private location, perfect for kayaking and paddle boarding. Features include 3 bedrooms including second floor primary en-suite with water views, 2 additional guest bedrooms, 2 additional guest baths and plenty of living space overlooking Goose Creek. Spacious bright kitchen, dining area with doors to waterside deck where you will experience beautiful sunsets. The perfect retreat for your summer fun or any other time of the year. Close to all North Fork amenities. Permit # 1023

Bring your swim suit, flip flops, and summer vibe! This amazing property located in a private beachfront community across the street from a beautiful sandy bay beach. The community is set far off the main rd providing a great ambience of being away from it all! Great place to relax, boat, entertain, dine al fresco, and all things fun in the sun. Lovely updated, immaculate home with 3beds and 2 full baths, office space, living room, dining room, outdoor deck with bay views! Pack some extra clothes, you will not want to go home!

Southold, North Fork - artful cottage located in Southold by Founder's Landing Park/Wharf House. Opposite a fabulous bay beach sits this unique, furnished, one bedroom residence. Full kitchen with dishwasher, bright and sunny living room, comfortable bedroom... home is heated by natural gas. Park like property with outside sitting area. Privacy and pet friendly. Enjoy life on the east end in this furnished home ready for you and convenient to area restaurants, wineries, and all the North Fork has to offer. Permit #0107

Spacious Open Floor Plan Newer Home. Inground Pool with Built in Hot Tub and Blue Stone Pool Surround. Screened Porch Overlooking Pool Area. Nice Yard. Wood Burning Fireplace. Good Wifi. Long Island Sound Beach and Historic Lighthouse Museum and Park Several Doors Away. Summer 2024 - Memorial Day through June $30,000. Off Season Until End of April 2024 at $10,000 Per Month (Single or Multiple Months Rental Considered). Permit #0537.

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.

Southold Goose Creek Waterfront. Immaculate sun-filled home with all you will need to relax and enjoy summer. Large living room, and dining room. Well equipped Kitchen with sliders to deck, Den with amazing water views. Ensuite bedroom with water views, 2 additional bedrooms and bathrooms. Furnished deck and large yard. There is a dock to fish, boat, paddle board or kayak (2 included) from your own dock. A perfect retreat close to all the best of the North Fork. Rental Permit 0691

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

Cozy Northern White Cedar Log Style Chalet With Heated Saltwater Pool. It is the juxtaposition between the rustic qualities and the elegant essence of this home that makes it so unique! Covered Wrap Around Porch. 2 Car Garage Attached, 1 Detached. Open Floor Plan. Two Spacious Bedrooms, The Primary Is En-Suite. Extra Loft Style Bedroom With Two Single Beds. Two Full Baths. Unique Smoke House. Appointed Details Inside This Home Were Skillfully Created By The Hands Of A Master Craftsman. Tucked Away On An Acre Property With Ample Privacy. The Perfect Home For Those Seeking A Secluded Vacation On The North Fork. Close Proximity To A Private Beach(Cedar Beach), Easy Access To The Water For Kayak Enthusiasts And A Ramp For Launching Small Crafts. Very Close To Goose Creek & Peconic Bay. Be Part Of What The North Fork Has To Offer: Pristine Beaches, Delectable Restaurants, Local Produce & A Burgeoning Wine Country. Southold Town Rental Permit #1016. May = $4000 per 2 week stay) (June = $5000 per 2 week stay) (July = $7500 per 2 week stay) (August = $10,000 per 2 week stay) (September = $9000 per 2 weeks) (October Through April = $3500 per 2 week stay)

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.

2024 Rates July $6,750.00/week (two week minimum) or $27,000.00 for the month: Brand New Modern Farmhouse Completed in 2021 and located in the heart Hog's Neck in Southold Hamlet. This home features an impressive 20x50 heated pool w/ electric cover, out door shower and sprawling paver patio. The interior is open and airy w/ Chef's Kitchen outfitted with Thermador appliances, large living room with built in shelving, gas fireplace and formal dining room. All four bedrooms are located on the second level: 1 Primary En-suite, 1 Junior Suite, 2 Guest Bedrooms and Full Hallway Bathroom. You will enjoy being within close proximity to Goose Creek, South Harbor Park Beach and Southold's vibrant business district!

This soothing beach house is so Zen, you will feel like you are at a spa retreat! Peaceful and perfectly appointed, the backyard features a fabulous lagoon style pool, with a waterfall and hot tub, an amazing outdoor kitchen and bar, bathroom and outdoor shower! 3 bedrooms, 2 baths, including a spacious primary suite with a gorgeous spa like bathroom. All this and steps to the association beach! Surrounded by marinas, award winning vineyards, restaurants, farm stands & great shopping. Make this absolutely mint home your North Fork summer rental, you will not want to leave! Rental Permit #1002

Welcome to your future summer retreat! This beautiful newly built home offers the perfect blend of comfort and luxury, featuring 4 spacious bedrooms and 4 full baths. First floor primary bedroom with luxurious ensuite bathroom. Inside, you'll find ample space and modern amenities that cater to your every need. However, what truly sets this property apart is the outdoor paradise waiting for you in the backyard. Immerse yourself in the heated saltwater pool or unwind in the relaxing hot tub - it's your private sanctuary. Don't miss the chance to rent this exceptional home and experience a lifestyle of unparalleled indulgence. Close to the beach!! Permit# - 0980

Room for All in this Spacious 6 Bedroom Luxurious Home with Gourmet Kitchen with 6 Burner Wolf Stove, Formal Dining Room. Large Living Room with Fireplace, a Separate Den and Large Bedrooms. Rainy Day Game Room and More in Lower Level. All set on 2.3 Acres with In Ground Pool, Nicely Finished Outdoor Space and Yard Area and Just a Short Distance to Kenneys and McCabes Beaches. Summer 2024 - June 1 to June 28 - $30,000 or $8,500 Per Week With Two Week Minimum. August 25 to September 8 (Two Weeks) $18,500; September $30,000 or $8,500 per Week With Two Week Minimum. Off Season - October through April at $15,000 Per month for Single or Multiple Month Rentals. Permit #0233.

Chic ranch at 600 Corey Creek Lane, Southold. Featuring a beautiful wood-burning fireplace centered in the living room with high vaulted ceilings. 3 beds and 2 baths complete this home with an updated kitchen flowing into the dining area. Outside is a generous-sized patio with a firepit perfect for unwinding and having a relaxing night. Great location; close to town with shops and restaurants plus access to Corey Creek at the end of the road and sandy South Harbor beach minutes away! Fully furnished. RP# 0512

Welcome to 1355 Watersedge Way a delightful Bayfront home located on Little Peconic Bay in Southold. Inside you have a spacious living room with a smart TV and a wall of sliding glass doors the lead out to the waterside deck, eat in kitchen, two bedrooms and one bathroom. on the lower level there is a family room with wet bar and access to the yard and outdoor shower, one bedroom, a full bath, and washer and dryer. The house is located next to a nature preserve with 300 ft. of beach providing easy access to the water/bay and plenty of privacy. Enjoy the spectacular views of the water and sunsets! MD TO LD $50k, June$12k, July $23K; August 1 to LD $24K, off season $7k for 30 days. House is available from May to November with a minimum of four weeks that does not need to align with the calendar month. RP# 0929

Permit #493 Newly Renovated Farmhouse Centrally Located In Southold With Easy Access By Bus, Train or Car. Enjoy Your Morning Coffee As The Sun Rises Over The Farmfield. Spend An Afternoon Exploring The Beauty of the North Fork, Soak in the Sun at one of the Beautiful Peconic Bay or Long Island Sound Beaches, Enjoy Live Music at Numerous Wineries and/or Breweries, Browse unique local finds at One of Many Antique and/or Quaint Shops, and Don't Forget to Stop by Our Bountiful Farm Stands. Cool Off With a Dip in the Heated Saltwater Pool, Enjoy Dinner Under the Stars and Reminisce Around the Fire Pit. Utilities Included. 10% Security & Exit Clean. Enjoy Summer On The North Fork!

NEW TO THE RENTAL MARKET! JUST A DREAM BOAT! NEWLY RENOVATED, LIGHT AND BRIGHT, BEAUTIFULLY APPOINTED, EVERY CONVENIENCE - 2 BEDROOMS, 2 BATHS. PLUS - CONVERTIBLE QUEEN SOFABED! BEAUTIFUL OUTDOOR DINING, FIRE PIT, PORCH, ENCLOSED SHOWER! PRICED RIGHT! STEPS TO POPULAR KENNEY'S BEACH - JUST BRING YOUR LITTLE RED WAGON AND STROLL TO THE BEACH AND ENJOY!

Located in a gorgeous Bay beach private community, just a stone's throw from Southold Bay. Waterviews from many rooms and the sprawling backyard. Immaculate, light filled, 5 bedroom/2 bath charmer with room for all. Features include walkout deck, a library, sunroom w/gorgeous Bay views, outdoor showerhouse. Super convenient to fine dining, shopping & wineries - just 5 minutes to either Southold or Greenport....even 3 stellar farm stands just up the road including a CSA. Farm to table heaven! Located within the Park District with access to Founders' Landing Park's treasured sandy Bay beach. Everything you need to enjoy your summer on the amazing North Fork! [Rental permit #0392; Expiration date 4/7/25].

Enjoy an experience on the North Fork of LI this summer. Whether a couple of weeks, a month, or the whole season, spend it nestled in a quiet spot that is near downtown Southold. Feel embraced by all the NOFO has to offer in this meticulously renovated, waterfront Cape, while enjoying the utmost in privacy and waterfront access. Step down into your own private swimming spot in clear Jockey Creek or enjoy your own private deep-water dock (bring your boat!). Kayak, canoe or paddle directly to Southold Bay, Shelter Island Sound and the extended fishing grounds of Greenport, Bug Light, Orient and beyond. Enjoy a quick ride into the charming downtown of Southold for elegant dining, shopping and easy access to LIRR/Jitney into NYC. Make lasting summer memories on this expansive idyllic, half acre, creekfront property which is perfect for quiet time, entertaining on the deck or play.

Permit 816. Beautiful New Construction In Private Beach Community. Creekfront Beach Access Along With 20x40 Heated Saltwater Pool. Ideal For Large Groups & Perfect For Entertaining, This Property Has It All. 8 Bedrooms And 7 Bathrooms Set On Lush Manicured Grounds, Provides Spacious Accommodations For Up To 16 Guests. Spend Afternoons Lounging By The Pool & Evenings Gathering With Family And Friends. Deeded Beach Rights, Minutes To Wineries & Just A Short Bike Ride To Restaurants And Shops In Town. Three 50amp lv2 EV Chargers Available. 14 Day Minimum.

The Perfect Place To Enjoy a North Fork Vacation! Beautiful New Home In Bay Front Community. Open Living Room With Fireplace And Flat Screen Tv. Open Dining Room And Kitchen With Easy Access To Covered Porch, Private Backyard w/ heated salt water inground Pool. Master Bedroom Suite On 1st Floor w/ king bed & smart tv, Additional Master Suite On 2nd Floor w/ king bed & smart tv, As Well As 2 Additional Bedrooms (1 queen, 1 w/ twin beds) And Full Bath. Short Walk To A Gorgeous Bay Haven Association Beach Right At The End Of The Street. . Renters Insurance required.

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

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, October $4500, November $3500, December $3500 Southold Town Rental Permit #0374

Impressive Goose Creek home with water views and large heated in-ground pool! This four bedroom, three bath house features a first floor primary bedroom with en-suite, a gourmet kitchen and open living space. The newly designed landscape is ideal for entertaining or relaxing. Enjoy its large fire pit and BBQ grill after an afternoon of Kayaking. Close to Southold town and Corey Creek Beach. Permit #0290

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