3 Bedroom Houses for Rent in Southold, NY

RP# R-2024-0042 Just moments to historic downtown Sag Harbor Village and killer sunsets at Long Beach and Sunset Beach in North Haven. This three bedroom two and half bath home has everything you are looking for in a summer stay. Open living and kitchen area, fireplace, vaulted dining area, first floor primary and two cottage style bedrooms on the second floor. Beautiful fenced in back yard offers a fire pit, outdoor shower for post beach days, two patio areas for evening dining and poolside entertaining. The 18 x45ft pool is perfect for morning laps and built in sundeck f

This amazingly totally custom-made renovated waterfront townhouse has it all plus an ideal location in the center of Sag Harbor Village close to all the amenities and enjoyments this wonderful waterfront village has to offer. The townhouse is elegantly furnished with Serena and Lily, featuring open spaces and high ceilings with floor to ceiling French glass doors opening to your own water view deck equipped with beautiful outdoor furniture, dining table and BBQ. The brand-new Chefs eat-in kitchen with island has everything you need as Thermador appliances, double oven/m

This classic updated 19th century home in the heart of historic New Suffolk is just moments to one of the North Fork's best bay beaches, plus two renowned local restaurants. It offers stylish living spaces; living room, den, dining room, eat-in kitchen, 3 bedrooms and 2 baths. Central air conditioning. Many antique details and original wood floors add to the charm. The wrap-around porch invites summer lounging, as does the spacious backyard. Available weekly during the Fall season with two-week minimum. Listing ID #860643

Property Status: Active 3 Bedroom/2 Bath Home with Heated Inground Pool and Several Beaches Nearby. Open Floor Plan and Vaulted Ceilings. Enjoy the Days of Summer on the Back Deck, Fenced Lawn and Pool. Several Nearby Beaches Too! Winter Rental (November 2025 to April 2026) Single or Multiple Months Considered at $5,000 Per Month. Summer 2026 - Memorial Day to Labor Day $45,000; June $12,000; July $16,000; August to Labor Day $20,000; Weekly $4,000 Per Week with Two Week Minimum. Permit #0586. Office Phone: (631) 477-2220 Copyright © 2025 OneKey MLS. All rights reserv

Property Status: Active Amazing Winter Rental with a Perfect Location in Sag Harbor Welcome to your new Sag Harbor lifestyle! Tucked away on a quiet cul-de-sac, this home is the perfect blend of peaceful living and prime location, just moments from everything you love about the Hamptons. The moment you step inside this charming beach cottage, you're greeted by an open floor plan bathed in natural light, creating a bright and inviting atmosphere. The design is all about effortless coastal living, with a seamless flow that leads you out to a spacious deck and a lush, level b

Property Status: Active Beautiful North Fork home within walking distance to the beach, as well as numerous vineyards, restaurants, and local shops. Upon entering this home, you will enjoy spacious living quarters full of natural light and comfortable furnishings. The perfect mix of modern comfort, the gourmet kitchen boasts stainless steel appliances, gleaming countertops, and a large center island with a breakfast bar. When you aren't hanging out in the living room, tuned into your favorite show in front of the heat of the fireplace, check out the equally plush bedrooms.

Property Status: Active Bucolic farmhouse on three lush acres in the heart of Cutchogue! This home features two large bedrooms each with queen beds and smaller third bedroom on second floor. There is a sunporch with sleeper sofa that would make an ideal work from home space. Outbuilding/shed on site can be used for storage. Half bathroom is on the first floor and a full bathroom newly tiled on the second floor. Available for year round rental. Rental Permit #0696 Office Phone: (631) 354-8100 Copyright © 2025 OneKey MLS. All rights reserved. All information provided by the

Property Status: Active This spectacular bluff-top home overlooking the Long Island Sound was designed for seamless indoor/outdoor living. As you enter the residence, you are instantly awestruck by the stunning floor-to-ceiling coastline views. From the spacious living room, step out to a large deck to better enjoy the expansive yard, which boasts a large pool, BBQ area for alfresco dining and a fire pit for unforgettable sunsets across the Sound. The home features three large bedrooms: one primary suite with a king bed, a second primary suite with a queen bed and a bunk r

Property Status: Active This is an amazing opportunity to enjoy everything that Sag Harbor Village can offer. This home is close to beautiful marinas, world-wide restaurants, and beaches, just a few minutes from Jitney and Main Street. This home features three bedrooms, two baths, a hot tub, a big backyard, a pool, inviting decor, a spacious living area with a fireplace, and a fully equipped kitchen ready for your culinary adventures. Basement is not included. Utilities are included in the price. Office Phone: (631) 725-0200 Copyright © 2025 OneKey MLS. All rights reserved

Property Status: Active MAGIC ON OREGON ROAD Romance, elegance, and the bucolic backdrop of Oregon Road make this home a standout! Nestled within a vineyard, this 3 bedroom, 2 bath vintage farmhouse charmer lies on 2 acres with an in-ground pool and endless vineyard views. Short distance to tasting rooms, farm stands, renowned restaurants, vineyards, and fantastic beaches that the North Fork is known for! $15,000 for July 16th - July 31st // $10,000.00 for January // $10,000.00 for February // $15,000.00 for June // $25,000.00 for July // $22,500.00 for Aug-Labor Day // $1