Long Island Vacation Rentals

Boutique Waterfront Home w Pool in the Heart of North Fork Wine Country
Long Island > North Fork > Southold
House, Bedroom(s): 4, Sleeps: 12
Newly Renovated Waterfront Home w/Pool in Southold, NY
$339 - $1,399 /Night
'The Gate House' on Beach front Estate
Long Island > North Fork > Greenport
Cottage, Bedroom(s): 2, Sleeps: 4
Cottage, 2 Bedrooms + Convertible bed(s), 1 Bath, (Sleeps 4]
$71 - $1,000 /Night
Summer Retreat w Dock on Inlet has Activities for All from Kayaks to Vineyards
Long Island > North Fork > Mattituck
House, Bedroom(s): 6, Sleeps: 16
Tucked away on the Mattituck inlet on the North Fork of Long Island, most of our guests don't even know there are houses where our home is located.
$349 - $1,399 /Night
Newly Renovated Waterfront Home with Pool in the heart of North Fork
Long Island > North Fork > Mattituck
House, Bedroom(s): 5, Sleeps: 12
4 Bedroom 3 Bathroom Waterfront Home w/ Pool
$349 - $1,399 /Night
Beach and waterfront Estate - One of a Kind Vacation House
Long Island > North Fork > Greenport
House, Bedroom(s): 5, Sleeps: 10
Beach House Rental, 5 Bedrooms + Sleeping Porch, 3 Baths, (Sleeps 8-10)
$257 - $8,000 /Night
The Stella Beach House: Beachfront & Amazing Views
Long Island > North Fork > Wading River
House, Bedroom(s): 3, Sleeps: 6
3 Bedrooms, 2 Baths, Sleeps 6
$208 - $786 /Night
Cozy Seaside Cottage
Long Island > North Fork > New Suffolk
Cottage, Bedroom(s): 4, Sleeps: 8
The Cottage at Whitecap is part of a Historic Compound built in 1883 and is located in the heart of New Suffolk.
$325 - $975 /Night
SUMMER RETREAT: Pool + Beach + Dock overlooking the Peconic Bay in Greenport!
Long Island > North Fork > Greenport
House, Bedroom(s): 4, Sleeps: 10
4 bedrooms 2 bathrooms with views of the Peconic Bay. Includes a pool, dock and adjacent to the town beach! POOL COMING SUMMER OF 2025!
$400 - $5,000 /Night
Only 5 houses from the ocean. Check out our reviews!!
Long Island > Fire Island > Ocean Beach
House, Bedroom(s): 5, Sleeps: 10
All Rentals are for 6 nights 7 days. The last day is required for cleaning.
$889 - $1,195 /Night
Spectacular Mega 3 Story Beach Front home W Private Beach & Pool
Long Island > Sound Beach
House, Bedroom(s): 5, Sleeps: 10
Leave your worries behind at this luxurious 3 Story Beach Front Home with panoramic views.
$1,500 - $2,600 /Night
Welcome to discounted rates for the fall, OCEAN FRONT home, OBP,,5 BDRM
Long Island > Fire Island > Ocean Bay Park
House, Bedroom(s): 5, Sleeps: 12
The cabin has fabulous views. Enjoy your stay with family & friends. open plan living, dining,kitchen
$800 - $2,200 /Night
MAROONED! Fire Island! Great ocean views! Just steps to the beach!
Long Island > Fire Island > Ocean Bay Park
House, Bedroom(s): 4, Sleeps: 10
Modern, stylish beach house with grand ocean views. 4 Bedrooms, 2.5 Baths, (Sleeps 10-12).
$1,500 - $1,800 /Night

Discover and Explore Long Island

 

DISCOVER AND EXPLORE LONG ISLAND Anchored in the Atlantic Ocean just southeast of New York City is the East Coast gem of Long Island. Though perhaps best known for its vineyards and vast array of lavish summer vacation rental homes, Long Island is not only a haven for the celebrated rich and famous. With its wealth of white-sand beaches, sky-high surf and Eastern coastal charm, both shores of Long Island attract flocks of regulars and tourists alike, particularly in the warmer months. Set apart by its distinct blue, green and white color palate, Long Island is a summer vacation destination with a long nautical history, perfect for the seafaring soul.

 

Long Island Areas: Orient Point - I s perched on the very northern tip of the North Fork of Long Island. Accessible by automobile but most frequently by ferry from New London across the Sound, Orient is a sleepy... Read more
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