Condo holiday rentals in Southold

Sun Drenched Loft-City Living in the Country

Guests will enjoy a well appointed, spacious sunlit loft with easy access to everything from this centrally located gem. Situated in the heart of WHB's newly renovated Main Street, this 4 bedroom loft is walking distance to excellent restaurants, quaint boutiques, places of worship, and the Westhampton Beach Performing Arts Center. And our world class beaches are a mile away! The Loft on Main is a one of a kind place that is sure to impress and provide a wonderful vacation experience for all

2 BR Waterfront Autumn Escape in Wine Country

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

Hamptons Hideway

Well maintained two bedroom, one and one-half bath condominium. Spacious living room and dining area. Half bathroom, washer and dryer on the first floor. Sun filled private patio with BBQ and table and chairs. Light and bright second floor. Large Master bedroom with Cathedral ceilings Adjoining bath and second bedroom.. Long Island Railroad around the corner. Perfect Proximity to West Hampton Beaches and shops. Please reach out via message if you have any additional questions before booking.

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 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.

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

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.