Condo holiday rentals in Southold

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 a 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

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

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

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!

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.

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.

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.

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.

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.