luxury real estate for rent Southold, United States

Come enjoy this newly renovated summer home, situated on 2/3 of an acre and located in the Silver Beach vicinity. Close to many beautiful beaches and blocks away to gorgeous sunsets. This home is a wonderful rental with an eat-in-kitchen, living / dining room, bedroom en-suite with shower and 2 bedrooms with hall tub/shower. The dining area has sliding doors that lead to the yard with privacy and brick patio with seating and a gas grill. Spend your summer on Shelter Island and make wonderful memories. Off Season $3,500, June -$8,000 , July $12,000 , August $12,000, July/Aug. $20,000 , MD-LD-$28,000

Wake up each morning to the sweet sounds of birdsong in this charming 4-bedroom, 2-bath, nestled amongst rolling hills. Located .6 miles from coveted Wades Beach and Mashomack Preserve. This secluded property feels like a private sanctuary, surrounded by lush greenery, blooming trees, and vibrant summer flowers. The open-concept living-dining-kitchen area is perfect for entertaining, with a spacious layout that seamlessly flows onto a wrap around deck overlooking the fenced in yard. The house has a mirror image layout for the lower and upper floors, two bedrooms and one bath upstairs and the same setup on the lower level with each its own entry. Access to Coecles Harbor Marina pool. Seasonal Rates: May $7,500 , June $10K , July $15K , Aug-LD $17,500 , May-LD $45,000 , MD-LD $40,000

Escape to your private Cutchogue oasis this summer! This stunning home boasts four bedrooms, including two en-suite, and 3.5 baths, offering luxurious accommodations for your getaway. Unwind in the in-ground pool, relax in the sauna, or lounge on the wrap-around porch overlooking a tranquil creek. Two living rooms and an open-concept kitchen provide ample space for entertaining, while the wooded lot ensures complete privacy. With coveted Nassau Point beach access less than a mile away, sun and sand are just moments from your door. Book your stay and experience the ultimate summer escape! Seasonal Rates: June $15K , July $30K , August $30K , MD-LD $70K , September $15K

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.

2025 Rates: June $8K, July $12K, A1-LD $13K, September $8K, October $7K Charming Nassau Point Cape Cod. Enjoy sprawling private grounds with community beach access as you enjoy the summer months in this ideal 3 bedroom 2 bathroom escape. The main level features and open dining/, kitchen leading to wood deck, main floor bedroom, full bathroom and living room. The second floor features 2 additional bedroom and 1 full bathroom. Don't let this amazing East End retreat slip away!

2025 Rates: Sept $17K, October $15K. 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.

Beautifully and recently renovated ranch home near Circle beach in Noyac with vaulted ceilings, open kitchen, TV room, 2 renovated bathrooms, central air, just about everything you need before you head to the beach! Close to Sag Harbor, Long Beach, restaurants and marinas.

**2025 Rates** May 23 - June 30: $18,000; July: $20,000; August 1 - Labor Day: $22,000; Memorial Day - Labor Day: $55,000. Welcome to the 123 Sterling Boat Lofts! This exceptional property, situated on Sterling Harbor in the heart of Greenport Village, represents the perfect East End retreat. Thoughtfully designed with a spacious open floor plan, this third-floor corner unit offers stunning water views from every room, blending convenience with stylish flair. In addition to the loft, you will enjoy access to a private first-floor office space, complete with a lounge and home gym overlooking the bay and harbor. An exclusive boat slip is also included, accommodating a boat up to 30 feet in length. Don’t miss out on this remarkable opportunity—make it yours today!

This privately located home is waiting for you to come and enjoy! Just minutes away from the Village of Sag Harbor, restaurants and the bay beaches, this home features 4 bedrooms, 4.5 baths with an open concept. The main floor offers a master bedroom with master bath, a beautiful kitchen, dining and living room, as well as a family room with a fireplace and a powder room. The second floor includes 3 bedrooms, 2 full baths. The basement is finished with gym equipment, den/office area. Outside is your beautiful deck with plenty of room for entertaining, a hot tub and heated in ground pool., Additional information: Lease Term: July 2025 $40K, July-August 2025 $75,000, August 2025 $40,000

Available 2025: April: $12,000, May: $17,500, June: $22,500, July: $35,000. 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.

2025 Rates are as follows: May 1 - 22: $10,000 or $3,500 per week; May 23 - June 27: $20,000 or $5,000 per week; July 13-31 $20K; Sept 4 - 30: $20,000 or $5,000 per week: 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.

2025 Rates: May $25,000.00; September $26,000.00 October $23,000.00. Experience North Fork summer living in this newly constructed gem! Nestled in the sought-after Stirling Eastern Shores community, this impeccably designed modern farmhouse offers exclusive access to a private Long Island Sound beach, just a five minute walk from the property. Step inside to discover a light-filled and meticulously styled interior adorned with contemporary finishes and furnishings. The heart of the home is the chef's kitchen seamlessly integrated into the Great Room and anchored by a cozy gas fireplace. On the first floor, you'll find a convenient half bath, a junior en-suite bedroom, a spacious mudroom, and a sizeable 2-car garage. Ascend to the second level to encounter two additional guest bedrooms sharing a full bathroom, along with a stunning primary en-suite bedroom. The primary bath boasts a luxurious double vanity, a walk-in shower, a soaking tub, and an expansive walk-in closet for added convenience and indulgence. Outside, the property showcases a captivating landscape featuring a sprawling stone patio enveloping a 20x40 heated salt-water pool, complemented by an outdoor shower - an ideal setting for hosting gatherings and enjoying the summer sun.

2025 Rates May 23-Sept 1 $65K, May 1-21 $5K, May 1-30, $10K, June 15K, July $23,500, A1-LD $25K, 9/1-30 $7,500, October $7,500: 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., Additional information: Appearance:Pristine,Interior Features:Combo Kitchen,Lease Term:August-Labor Day,Flexible,July,July-August,June,Memorial-Labor,Monthly,Off Season

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. Permit# 0026.

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.