Condo vacation rentals in Southold

A private beach stretches along the coastline, with soft sand and patches of greenery. A wooden pathway leads from the grassy area to the water, while several beach loungers are positioned facing the shore. The gentle waves of Long Island Sound meet the sandy beach under a clear sky.

4.88 out of 5 average rating, 127 reviews

Seaside Summer Escape –2BR Waterfront Condo w/Pool

Overlooking the Long Island Sound, this oceanfront condo is the ultimate escape. Bask in the sun on your private beach or unwind on the waterfront deck with breathtaking views Minutes from the town center, you’ll find local farms, award-winning wineries, gourmet restaurants & charming shops ⚓️ Explore Greenport: A historic seaport with coastal charm & rich culture 🏖 Premium Amenities – Waterfront deck, private balcony, grills, pool, private beach & parking ⛴ Ferry Access to Shelter Island & CT

4.88 out of 5 average rating, 17 reviews

An open-concept kitchen and living area features a central island with bar seating, surrounded by modern appliances and white cabinetry. Natural light pours in through large windows, illuminating a cozy seating area with a sofa and dining space, creating a welcoming environment.

Condo in Bridgehampton

Bridgehampton w/ Pool steps to town 3 bd 2.5 Bath

Beautiful duplex corner townhouse unit completely renovated in 2021 & in the heart of Bridgehampton Village. 2 min walk to shops, restaurants, main street and a bicycle ride to the beach. Situated all the way at the end of the building it provides ample privacy with Pool open July 4 - Labor Day only. Free parking (2 spots) w/ extra guest parking. Central air conditioning, private patio, ring doorbell/cam, self check in, curated kitchen w/ all supplies. Linens, towels, soap & shamp included

A serene ocean view features gentle waves lapping against a rocky shoreline, with a soft sunset illuminating the sky. Silhouettes of distant rocks and subtle ripples on the water enhance the tranquil atmosphere.

4.92 out of 5 average rating, 141 reviews

Beachside Waterview 2Br Condo w/ Pool in Greenport

Relax in a pristine 2Br condo with ocean & pool views. Our remodeled apartment is part of high-end development nestled on LI Sound, just minutes from downtown Greenport. Sip a glass of wine while watching sunset, catch some rays on the beach or deep in the pool. 2 bedroom condo with ocean view, beach, and pool (seasonal) Comfortably sleeps 6 Private beach access year-around Pool (seasonal) Functional kitchenette 2 bathrooms, all toiletries Linens and towels are provided Smart TV AC/Heat

A patio area features two gray armchairs positioned beside a small table. An American flag waves gently above the space, framed by green grass and a waterfront view showcasing boats at a dock beyond. The scene reflects a calm and relaxing outdoor atmosphere.

5 out of 5 average rating, 6 reviews

Water front, sunsets, sail boats, Wi-fi, birds

Freshly renovated, this sunny 2 bed 2 bath condo features cozy wood burning fireplace, central air, amazing waterfront view with patio, tennis, pool, parking, BBQ and beach launch for water sports. Kitchen is outfitted with all cooking, baking needs. Wine fridge, Kuerig, French press. Includes wide screen TV, Sonos, 1 gig WIFI, HP all-in-one printer. Peaceful tree lined neighborhood 2 blocks from all that Greenport has to offer. Includes boat dock!

Several white lounge chairs are arranged on a sandy beach, facing a calm body of water. The sky above is partly cloudy, allowing for diffused sunlight to reflect off the water's surface, enhancing the serene coastal environment.

4.89 out of 5 average rating, 154 reviews

Beautiful Waterview Condo on the North Fork of LI

Waterview luxury suite accommodates up to 6 guests with two bedrooms and two bathrooms located on the North Fork of Long Island at The Cliffside Resort Condominiums in Greenport, New York. This location is minutes from town as well as wineries and centrally located to the ferry which can take you to Shelter Island and the South Fork. The resort is well maintained with a pool , BBQ grills and private beach access as well as ample parking for guests.

4.89 out of 5 average rating, 35 reviews

Condo in Old Lyme

Hatch at Soundview · Beach+OceanView+Sunrise

Welcome to Hatch at Soundview 1 bedroom at Old Colony Beach in Old Lyme, Connecticut. Located just 1 block from Old Colony Beach! The ultimate getaway for a couple seeking relaxation and outdoor beach adventures. This 2nd floor corner location is ideally situated with a panoramic water view, queen memory foam bed, full kitchen with 4-person dining area, w/ 55" TV, and AC. Walk 1 block south and you are at the beach!

A living room features a blue sectional sofa with decorative pillows, positioned beside a modern glass coffee table. A flat-screen TV is mounted above a stone fireplace, and large windows provide views of the surrounding greenery. Warm lighting creates a cozy atmosphere.

4.84 out of 5 average rating, 106 reviews

Beautiful condo on Long Islands Northfolk

This condo is beautifully decorated and has a wonderful stone fire place. Gorgeous shiplap walls with Navy accents. There is also a new deck and wonderful dinning set outside. This unit has capabilities to be handicap accessible. Both bedroom have private bathrooms. The living room sectional opens up to a full sleeper making this condo able to sleep six people. All rooms have flat screen smart tv's.

5 out of 5 average rating, 36 reviews

An outdoor seating area features a wicker sofa and two matching chairs, adorned with green cushions and decorative pillows. A small round table stands nearby, while a fire pit is positioned at the center of a stone patio surrounded by a natural stone wall.

Condo in Mount Sinai

1856 Trading House close to water

Located in quaint, quiet Historic Mount Sinai. 2mi to Cedar Beach, 2mi to Downtown Port Jefferson, and 2mi to Train Station. Converted convent built in 1856 w/winter water view, across the street from Mt. Sinai harbor, low tide clamming and high tide kayaking and fishing. Next to Episcopal Friary. Antique hardwood floors. Parking available on Premises. Yard Access.

4.78 out of 5 average rating, 23 reviews

A bright living area is showcased with soft carpeting and wooden beams along the ceiling. A white dining table and chairs are featured, with a kitchenette in view. Sunlight streams through a skylight and large windows, illuminating the space.

Condo in Hampton Bays

Waterfront Elevated Bungalow - Spectacular Views

Bright, skylit, sunny, and clean bay-front apartment with gorgeous water and sunset views. Large private wraparound deck, spacious living room, kitchenette, two full bathrooms, and a California-king size bed. Less than 250 feet from bay and 3.5 miles from ocean beaches! Two week minimum. Large discount for full summer stay.

Condo in Downtown New Haven

A fully equipped kitchen features stainless steel appliances, including a refrigerator and range. Granite countertops provide ample workspace, and a window allows natural light to illuminate the area. A small dining space is visible near the sink, enhancing functionality.

4.84 out of 5 average rating, 287 reviews

Stunning, Spacious, Spotless. Close to Yale.

This is a gorgeous two bedroom apartment. The main bedroom has two twin beds, a walk-in closet, and its own private bathroom. The second bedroom has a queen size bed and its own private bathroom and closet. Fully equipped open kitchen. Living dining space. In unit washer/dryer.

Top guest favorite

A serene sunset view over the tranquil waters of Long Island Sound is captured from the private balcony. Soft hues of orange and pink reflect off the calm surface of the sea, while the lush green foreground frames the scenic landscape.