
Condo vacation rentals in Southold
Find and book unique condos on Airbnb
Quick stats about condo rentals in Southold

Total vacation rentals
Explore 20 vacation rentals in Southold

Nightly prices starting at
Southold vacation rentals start at G$27,185 GYD per night before taxes and fees

Verified guest reviews
Over 1,340 verified reviews to help you choose

Family-friendly vacation rentals
20 properties offer extra space & kid-friendly amenities

Vacation rentals with a pool
10 properties feature pools

Wi-Fi availability
10 of Southold vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Southold rentals

4.8 Average rating
Southold stays are highly rated by guests—averaging 4.8 out of 5!
Top-rated condo rentals in Southold
Guests agree: these condos are highly rated for location, cleanliness, and more.

The Bridge at Soundview · Beach+OceanView+Sunrise
Welcome to The Bridge at Soundview Penthouse at Old Colony Beach! The ultimate getaway for a family seeking relaxation and outdoor adventures. This 3rd floor location is ideally situated with a direct water view, and you will have exclusive access to the entire floor with a private top floor observatory looking over the water. We feature 4 BR, 1.5 bath, a convenient kitchen, and a comfortable living room with a large - private outdoor seating areas. Walk 1 block south and you are at the beach!

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.

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 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.

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.
Popular amenities for Southold condo rentals
Weekly condo rentals

Greenport Getaway at Cliffside Condos

The Anchor at Soundview · Beach+Ocean+Sunrise

Beautiful condo on Long Islands Northfork

Waterfront Escape | Private Beach, Pool & Views

Beautiful Waterview Condo on the North Fork of LI

1856 Trading House close to water

Waterfront Escape | Private Beach, Pool & Views

Beachside Waterview 2Br Condo w/ Pool in Greenport
Pet-friendly condo rentals

1856 Trading House close to water

Beautiful condo on Long Islands Northfork

1856 Trading House w/ walk to water

Cute cottage apartment upstairs in Sag
Condo rentals with a pool

Cliffside Resort Poolside Condo A204

Modern Two Bedroom Apartment. Beach Ready!

Charming Bayfront Condo

Bright and Airy One Bedroom Apartment in the Dunes

Charming 2 Bedroom Apartment with Beach Amenities!

Cliffside Resort Poolside Condo A106

Newly Renovated Modern Townhouse w/Pool & Tennis

Waterfront Escape | Private Beach, Pool & Views
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- Rentals with beach access Southold
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- Beach
- Yale University
- Cooper's Beach, Southampton
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- Charlestown Beach
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