luxury real estate for rent Southold, United States

2025 Rates: June $30,000, July $60,000, July-August $125,000 and August-Labor Day $65,000. This stunning two-story home sits on 3.44 acres of beautiful lawns and trees, featuring a circular driveway and a double-arched covered porch with bluestone patio. Inside, the foyer opens to a light filled dining room and great room with 10 foot coffered ceilings, exquisite details, and an elegant chef's kitchen equipped with Crownpoint custom cabinetry and top -of-the-line Wolf and Sub-Zero appliances. French doors lead to a covered porch overlooking the pool and yard. The second floor has 3 bedrooms each with a private bath and 9 foot ceilings. A separate staircase leads to a den with pull out sofa, wet-bar with ref/freezer and it's own full bath. Additional features include a full house generator, alarm system, and two smart tv's. This home is close proximity to Wades Beach and Mashomack Preserve.

Available 2024: May $9,500, Memorial Day-Labor Day $83,500, June $24,500, July $29,500, July-August $59,000, August-Labor Day $29,500, September $14,500, October $9,500. Available off season for $6,000 per month November 1, 2023, through April 31, 2024. Paradise along the Long Island Sound. This pristine and newly renovated home is a very unique offering w/ straight shot sunset views over the LI Sound and private beach access just 100 yards from the house down a sandy path through the Peconic Dunes. The home features an impressive primary en-suite overlooking the Sound, 2 guest bedrooms w/ shared hallway bathroom, and an additional flex room that can be used for sleeping quarters or as a remote home office. High soaring ceilings on the main floor allow for sun soaked exposure throughout the Great Room and impressive large Chef's kitchen. Truly a special property that will offer an authentic North Fork Summer experience! Permit# 0874.

Available 2024- MD-LD $53,500, May $6,000, June $12,500, July $19,500, July-August $41,000, August-LD $21,500, September $8,000, October $6,000: Escape to sweeping dunes along the Long Island Sound in the Hamlet of Peconic. This restored 1940's beach cottage offers charm, character, modern amenities and easy summer water-front living. The grounds are sprawling, incredibly private, will offer breath taking sunset and the ideal setting for summer stargazing. The interior features 3 bedrooms, 2 bathrooms, 2 living rooms and updated bathrooms and kitchen. Enjoy this serene setting nestled away along some of the North Fork's most desirable beach fronts.

Live in the heart of the action with this beautiful, newly renovated 2-bedroom, 1-bathroom apartment in Greenport Village. This furnished and fully-equipped haven is perfect for anyone seeking a convenient and comfortable place to call home. Available for Seasonal Rent; July $6k, August $6k and Year Round Rent; $3,500

2024 Rates: September $15,000 and October $10,000. This property is a stunning waterfront home located on West Cove in the exclusive Nassau Point area. Offering breathtaking views of the Great Peconic Bay, Robins Island, and New Suffolk, this home exudes charm and sophistication. The main level boasts two spacious great rooms, an enclosed three-season room, an eat-in kitchen, a dining room, and a primary en-suite bedroom. The finished basement includes two additional bedrooms, a full bathroom, and a media room, while the second floor features two more bedrooms and another full bathroom. The property's grounds are beautifully landscaped and elevated, with a mahogany deck, stone patio, outdoor dining area, and stairs leading to a raised platform beach with a pergola, providing easy access to the Bay for a refreshing dip.

Classic contemporary style New Construction in the heart of Greenport Village. This 2900+ sqft offering features 4 wide white oak hardwood floors throughout w/ inviting Great Room, eat-in Kitchen and Junior Suite bedroom on Main Level. The second floor features an cozy additional den/media room with two generously sized guest bedrooms sharing a full bathroom, laundry, ample storage, a primary ensuite bedroom with walk-in closet and large walk-in shower. In addition to the 1st and 2nd floors is a partially finished basement with separate outdoor access already in place or as lower level gym or media room. For those looking for tremendous value and as central Greenport Village location, this is an absolute must see.

Newly Renovated Ranch Oasis in the Heart of the North Fork! Embrace the laid-back luxury of living in this stunning 3-bedroom, 2.5-bathroom ranch, completely renovated and move-in ready! This beautiful home is ideally situated in the central part of the North Fork, putting you within easy reach of everything this vibrant region has to offer. Stroll to charming shops, hop on public transportation to explore further, or indulge in fresh produce at farm stands - all just moments away. Craving a taste of the good life? World-renowned vineyards, delectable restaurants, and the picturesque Nassau Point Beach are all at your fingertips. This prime location also grants you access to all Southold town beaches, ensuring endless summer fun. Don't miss this opportunity to live in the heart of the North Fork's magic!

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.

Vacation at this spectacular, completely renovated 4 en suite bedroom home this summer located in the desirable Fleet's Neck neighborhood with 2 gorgeous beaches moments away! Entertain in the open concept living area featuring a large island overlooking the family and dining area, perfect for large gatherings. The first floor features 2 bedrooms with 2 full baths with glass sliders leading out to the deck. Downstairs has 2 more ensuite bedrooms with glass sliders leading out to a patio. Soak up the sun and relax by the saltwater pool, rinse of the sand with the spacious outside shower or enjoy the patio where there is plenty of room to entertain throughout any time of the day. Available April: $12,000, May: $17,500, June: $22,500, July: $35,000, August - LBD: $40,000 and Memorial Day - LBD: $95,000

Summer 2024 Rates: May24-June30 $20K, July2-Aug1 $30K, Aug2-Sept3 $35K, Sept4-Oct4 $15K: Rare new construction on a quiet side street in Greenport Village, this modern luxury home is the perfect base to explore the beaches, wineries, and farm-to-table dining of the North Fork. Walking distance to downtown Greenport and a short drive from all the major North Fork sights. Or just whittle away your days enjoying the amenities of your luxurious home retreat. Lounge in your heated saltwater pool while sipping a cold drink. Curl up with a book in front of your gas fireplace. Catch up on sleep surrounded by plush bedding on your memory foam mattress. Immerse yourself in the low-key North Fork lifestyle at your private Greenport Getaway.

2024 Rates: May 1-20 $5K, May 24-June 30 $15K , July 3-30 $20K , August-LD 2-LD $22,500, September 5-30 $6,500, October $7,500, MD-LD $57,500: Pristine Mid Century Modern Waterfront with 200' Of Private Sugar Sand Beach! Property Features Breathtaking Views Of Robins Island, Southampton And Nassau Point. Chic Furnishings Adorn This Lovely Home Along with Interior Panoramic Views Of The Great Peconic Bay. Open Living Space with High Ceilings, Master Suite, 3 Additional Bedrooms, An Eat-In Kitchen And 2.5 Baths.

Also available Nov 1 - Apr 30 $36K This beautiful waterfront home in Sag Harbor is now available for rent for the first time. Sweeping views of the Little Narrows section of Sag Harbor abound and are afforded from many areas of the property. Highlights of the first floor include a large living and dining area that overlook the water, a separate kitchen, a charming study surrounded by windows, a guest room and hall bath. Upstairs is another guest room and bath and the primary suite, which has its own bath, a private veranda and is surrounded by windows and expansive water vistas. The backyard has a covered porch, an outdoor shower, a large deck and a long dock out to the bay, which is wonderful for boating, kayaking and even a swim. This waterfront gem is very close to Sag Harbor Village and its many wonderful parks, shops and restaurants. Rental Reg. # RP230721 Reg. Expires 6/15/2025 EH RR #: RP230721 Rental Terms: Winter Season: $33,000 Per Month Two Weeks: $35,000 August - Labor Day: $60,000

Looking for a resort like retreat just outside of bustling Greenport Village? Look no further! This 6 bedroom, 4.5 bathroom stunner offers everything you could ask for and more. From 3 en-suite bedrooms to an open floor-plan with high-end appliances and a killer in-ground pool/hot tub combo, this property serves as the ideal summer rental. This rare offering is also just a short walk to a sugar sand bay beach, close proximity to Islands End Golf Course, local wineries, farm stands and much more!, Additional information: Appearance:Pristine,Interior Features:Guest Quarters

Relax and enjoy this beautifully appointed bay front house w/ private beach and stunning views of Orient Harbor, Bug Light and Shelter Island. Moor your boat in the bay; kayak, swim, fish or chill on the decks and porches. Basement game room w/ Ping-Pong, TV and games. Conveniently located near shopping, restaurants, ferries, farm stands, vineyards.

Introducing a beautifully updated 3 bed, 2 bath home, quietly nestled on .45 acres. This residence features a spacious living room perfect for relaxation, a modern, well-equipped kitchen, a cozy den/bonus room for added versatility, and brand new baths. The home also includes a beautiful sunroom that opens up to the backyard, where you'll find spacious patio areas, pool with a brand-new liner, hot tub, an outdoor shower, and a serene sauna-ideal for enjoying the outdoors year-round. A partly finished basement and large shed offers additional space for storage or recreational use. Ideally located just minutes from Sag Harbor, Southampton, and Bridgehampton, this home provides convenient access to world-class ocean and bay beaches, as well as renowned local shopping and dining. A perfect Hamptons retreat combining comfort, privacy, and prime location.

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.

Enjoy a beautiful airy and bright mint condition Bay Front Orient Contemporary home, perfect for relaxing and entertaining. This 4-bedroom 4.5 bath home has gourmet kitchen, fireplace, open common space for easy entertaining. First floor has access to bay side screened porch from living room and den (or 4th bedroom with full bath). Second floor master bedroom and a guest bedroom open onto upper bay side deck, a third bedroom with full bath completes the layout. Private stairs to the beach and deeded beach rights to association Bay beach just a short walk from the house. Property is close to all village amenities: Country Store, Post Office, Marinas, Bay and Sound beaches. Offered Apr $10,000; May $12,000; June $15,000; July $35,000; Aug $35,000; Sept $20,000; Oct $15,000; Nov $10,000. Permit# 1020.

2024 availability includes: Any 2 weeks in May: $3,500, June: $12,000, July: $18,000, Aug 1 - 15th: $10,000, and Sept 23-Oct 7th: $5,000. Escape to the North Fork and enjoy the perfect blend of comfort & coastal living in this meticulously maintained 3-bed, 3-full bath home. As you step inside, you'll be greeted by living space adorned with nautical-inspired decor, plenty of natural light, and a gas fireplace. The fully equipped kitchen is a chef's delight, with stainless steel appliances and ample counter space for culinary creations. The open-concept design ensures a seamless flow between the kitchen, dining, and living areas, creating an ideal space for entertaining. Upstairs you'll find the primary king suite with views of Mattituck Inlet and a private spa-like bathroom off the expansive walk-in closet. Two additional well-appointed bedrooms, one w/ a queen bed, the other w/ a full bed, provide plenty of comfort for family members or guests. There's a pull out couch for overflow as well. Theater/media room in the basement, perfect for the rainy days or movie date nights. As you venture outdoors, a pristine landscaped backyard awaits, complete with a patio for outdoor dining, an outdoor BBQ area with a pizza oven, and a cozy fire pit. The home also has a pull out couch for additional overflow, two separate work spaces for those who need to work while on vacation, and split zone Sonos speakers throughout the house and in the backyard. Conveniently located near sought after Love Lane, several renowned wineries, farm-to-table restaurants, several local beaches, and more. Seize the opportunity before someone else does! 2 week minimum required.