2 Bedroom Houses for Rent in Southold, NY

RR#:RP240326 Escape to the tranquility of waterfront living with this 2 bedroom 2 bathroom cottage - perfect for those who crave stunning sunsets, serene waters and nature. Nestled right on the water this cozy haven offers endless relaxation and summer entertainment, whether you are hosting friends or enjoying a quiet retreat. Amazing sunsets - Enjoy breathtaking views every evening from your outdoor covered porch or private patio where you can dine al fresco while the sun sets. Boating -Step outside to your own private dock where you can kayak, boat or paddle right

Property Status: Active Cutchogue, North Fork work-live annual rental features 2 plus bedrooms, 2.5 baths and lots of light in contemporary farmhouse style. Open floor plan features large living room with decorative wood stove, dining room, eat in kitchen with sitting area and deck access. Bonus room and 2 car garage on first floor PLUS upstairs large owner's suite with private full bath, and additional bedroom and loft plus a second full bath. A perfect house in the country with ample yard for entertaining under a pergola. All steps to the village of Cutchogue, area beach

Property Status: Active Perfect summer cottage. Location can't be beat! A stone's throw to serene Pequash beach. Nestled in quiet Fleet's Neck with 2 bay beaches within walking distance. Well maintained home. Available for summer or short term off-season rental., Additional information: Lease Term:August-Labor Day,Flexible,July,July-August,June,Memorial-Labor,Off Season,Weekly Rent Amt:2000 Office Phone: (631) 765-6000 Copyright © 2025 OneKey MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should b

Property Status: Active Charming 2-bedroom, 1-bathroom summer cottage nestled in East Marion's sought after Gardiner's Bay Estates community. This delightful home offers the perfect blend of tranquility and community spirit, where life slows down. During the 4th of July Holiday, you'll get to enjoy the little red wagon community parade, reminiscent of a simpler time. The private beach community boasts access to a private sandy beach, mooring, bulkhead space and a swim platform. The outdoor patio offers a quiet retreat for alfresco dining while the screened-in porch prov

Rental Registration #: 25-159 New to the market, completely renovated Cottage with 2 bedrooms, 1 bath, all new appliances, wood floors, new roof, new cedar siding and new AC condenser. Delivered unfurnished, the property is ready to move-in for annual tenant. Listing ID: 874973

Now available for year-round, winter 2024/25 and the summer season 2025, this house is an absolute jewel. On a quaint Village street, desired by many. 2 bedrooms, 2 bathrooms. Short distance to ocean and the center of the Village. Listing ID: 899340

Property Status: Active NEWLY REDUCED PRICE FOR THE SEASON-GREAT HOME, GREAT VALUE!! ** MUST SEE ** Beautifully and Tastefully, Fully-Renovated 2 Bed, 3 Bath home featuring a stunning, private landscaped yard with a 20' x 40' Heated, Saltwater Gunite Pool. This home will make your Summer of 2025 an absolute delight, as it is completely ready for you and your bags! You will find an abundance of options to fill your days, as the Town of East Hampton is renowned for its wonderful Beaches, Shops, Restaurants, Theaters and Cultural Events. This home is easy to maintain, an

Enjoy the perfect location for convenience and coastal living. This charming 2 bedroom and 1.5 half bath home just a few blocks from Main Street's shopping, restaurants and the ocean beaches. Step inside and be greeted by the open plan with wood-burning fireplace, multiple oversized glass doors open to central deck and garden allow for one story living at its best. Designer owner touches throughout create a warm and inviting atmosphere. The recently renovated kitchen and fresh furnishings will make for a great summer experience on one of the most desirable streets in Sout

Newly renovated 5-star hotel-quality 2-bedroom, 2.5-bathroom luxury townhouse located south of the highway, just minutes from the Village and the best beaches in the Hamptons. This exquisite home features a piano, tennis and pickleball courts, and multiple pools set on beautiful grounds, with a private, quiet backyard offering all-day sunny exposures. Enter into the airy double-height foyer and immediately notice the attention to detail and craftsmanship. The first floor includes an 8-person dining area and an eat-in kitchen with quartz countertops and new stainless steel

Property Status: Active In the heart of Southampton Village is this newly renovated classic Hamptons beach cottage. Offering 2 bedrooms and a full bath with an open living/dining area and fully equipped kitchen with island seating. Washer/ Dryer and central air along with a garage complete this charming residence ready for year round living. Office Phone: (631) 283-5050 Copyright © 2025 My State MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

Updated, open concept, 2 bedroom ranch in Bayview Pines with private beach access in a lovely community. Fenced, private backyard

Property Status: Active Located only 1.3 miles from the iconic Shinnecock Hills Golf Club, this adorable and stylish 2-bedroom, 1-bathroom home is the ideal rental for the 2026 Shinnecock Open—or simply a relaxing Southampton escape. The interior features a newly renovated kitchen with stainless steel appliances, a comfortable living room, and both a family and sitting room for added space and flexibility. Thoughtfully furnished with charm and comfort in mind, it’s a perfect home base for summer living. Step out back to enjoy a covered porch overlooking a beautifully lan

Property Status: Active Bay View Estates in the next up and coming area in the Hampton's. Come visit this quaint beachfront community and enjoy the historical hamlet. The community is nestled between the south fork and the north fork where you can enjoy the best of both worlds. Brand New totally renovated in 2024, this 2 bedroom home located in Flanders is just a short distance to the private community beach, docking space available upon request . The home offers 2 Bedrooms, 1 bathroom Living Room and dining area with a brand new kitchen, a covered porch that leads into th

Property Status: Active Outstanding water views! Come watch the leaves change while enjoying this beautifully appointed luxury townhome in a gated community with only 12 units. Condo has primary ensuite with balcony, secondary ensuite, an open concept living area with large balcony, finished lower level with sliders to patio and laundry room. There is also a clubhouse with fitness room and community pool. All this within close proximity to restaurants, shops, beaches and all the south and north fork have to offer. Easy commute with jitney and railroad close by., Additional

Property Status: Active Stunning Townhouse w Tennis & Pool. Newly renovated 5-star hotel-quality 2 bedroom, 2.5 bathroom luxury townhouse. Minutes to the Village and the best beaches in the Hamptons. Piano, tennis, pickle-ball and multiple pools on beautiful grounds and a private, quiet backyard with all day Southern sunny exposures. Enter into the airy double height foyer and you will immediately notice the attention to detail and craftsmanship. The first floor includes an 8-person dining area, eat-in kitchen with quartz countertops and new stainless steel appliances whi

Property Status: Active Available to rent through May 31, 2026 with possible option to extend through the summer. This fully furnished 2 bedroom, 2 bath cozy cottage in Sachem Head will be the perfect place to enjoy all that this sought after beach community offers. First floor bedroom, large spacious living area with wood burning stove, light & bright kitchen, full bath & laundry room. Second floor is primary bedroom suite. A 'kick back and relax' covered front porch and quiet peaceful surroundings. Walk to association private beach and State owned Trolley Road Coastal Ac

Property Status: Active Oak Hills! Beautiful water views from most rooms. Two story cliff top setting with inground swimming pool. Hardwood floors, stainless steel appliances. 2 BR, 1.5 baths, primary bedroom with waterside balcony. Oak Hills sunset viewing platform and stairs to Long Island Sound Beach. Gorgeous sunsets, peace and quiet. Relax here all year round! Office Phone: (631) 722-5800 Copyright © 2025 OneKey MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verifi

Property Status: Active Beachfront Cottage on the Sound with private cliff for sunsets and sunbathing. 2 Bedrooms, 1 bath. Vintage charm with all modern amenities and updates. Cedar shingled artists retreat with beautiful waterviews. Screened porch, open deck, air conditioning, and hardwood floors. Spend your summer exploring all the North Fork offers. Visit the vineyards, beaches, boating and restaurants., Additional information: Appearance:Excellent,Interior Features:Separate Thermostat, Interior Features:Separate Thermostat Office Phone: (631) 722-5800 Copyright © 20