Apartment holiday rentals in Southold

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

Greenport Getaway at Cliffside Condos

Welcome to our Cliffside condo in Greenport, a comfortable 2-bedroom retreat perfect for families and friends. The home features a queen bed in the primary bedroom, two twin beds in the second bedroom. Enjoy easy access to the private beach, seasonal pool, BBQ on the great lawn and the most beautiful sunsets over the Long Island Sound. You’re just minutes from Greenport’s shops, restaurants, and vineyards, an ideal North Fork getaway to relax and unwind.

Water front, sunsets, sail boats, min stay 30 days

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!

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.

Waterfront Escape | Private Beach, Pool & Views

Overlooking the Long Island Sound, this beautiful waterfront condo is the perfect North Fork coastal escape. Enjoy peaceful mornings with panoramic water views, spend your days soaking up the sun on the private beach, and unwind on the waterfront deck as the sun sets over the Sound. Located just minutes from Greenport Village, you’ll be close to charming boutiques, local farms, award-winning wineries, and gourmet dining.

Beautiful condo on Long Islands Northfork

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.

Newly Renovated Modern Townhouse w/Pool & Tennis

Newly renovated townhouse minutes from main street & the beach. 2 bedroom, brand new kitchen & appliances, living room w/fireplace in beachy grey & cream tones will make you feel right at home. Includes a pool & tennis court steps out the front door. Less than a 10 min drive to Shinnecock Hills Golf Club, you can easily enjoy the upcoming US Open Championship. July:$23,000 August: $25,000

A Unique Piece of Paradise, Water Front pool

One bedroom Townhouse, sleeps four King Size Bedroom with views of Shinnecock Bay Living room with pull out queen sofa bed Newly renovated tile bathroom and kitchen In unit Washer/Dryer Fully equipped kitchen with new appliances and granite counter tops Flat screen TV's in both L/R and bedroom WIFI Linens and towels included Patio with grill Pool with deck overlooking Shinnecock Bay

1856 Trading House w/ walk 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.

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.

One Bedroom Apartment Nestled in the Dunes

Beautiful First-Floor Unit This beautiful first-floor unit is just a 1-minute walk to the heated pool and features a kitchen, air conditioning, and comfortably accommodates up to 2 guests (including kids or infants). It’s the perfect space for a peaceful and relaxing stay. Minimum 5-night stay.

Waterfront Condo C-204 at The Cliffside Resort

Water's Edge luxury suite with amazing waterfront views, Suite C-204, accommodates up to 6 guests (See The Space below) with two bedrooms and two bathrooms located on the North Fork of Long Island at The Cliffside Resort Condominiums in Greenport, New York.