Long Island Vacation Rentals

Steps from the Beach- dog-friendly, outdoor shower, renovated kitchen and master bedroom
Long Island > Fire Island > Ocean Beach
House, Bedroom(s): 5, Sleeps: 10
This super bright and beach-themed home is located in the Ocean Beach Village on Fire Island and only two-hundred feet from the water.
$350 - $1,900 /Night
Gorgeous 5 bdrm home with beautiful bay views in the heart of Greenport Village
Long Island > North Fork > Greenport
House, Bedroom(s): 4, Sleeps: 10
Enchanted home with beautiful bay views. This house has it all!
$550 - $1,500 /Night
Luxurious living in Greenport's private Rock Cove Estates on the Sound
Long Island > North Fork > Greenport
House, Bedroom(s): 4, Sleeps: 12
Luxurious living in Greenport's private Rock Cove Estates on the sound
Brand new 2 bedroom, Greenport Village, walk to town Marina Views!!
Long Island > North Fork > Greenport
Apartment, Bedroom(s): 4, Sleeps: 10
Beautiful marina views. Gorgeous chef's kitchen, hardwood floors throughout, marble baths, barn doors. Located in the village of Greenport, walk to town.
$550 - $1,500 /Night
Montauk House with Lake View
Long Island > Hamptons > Montauk
House, Bedroom(s): 4, Sleeps: 8
Main house
$450 - $1,150 /Night
Pet Friendly, Bayfront Retreat Close to Ocean Beach Restaurants & Shops
Long Island > Fire Island > Ocean Beach
House, Bedroom(s): 5, Sleeps: 12
Ocean Beach 5-Bedroom 2 Bathroom, Coastal Living close to town's dining, shopping & playground.
$900 - $1,500 /Night
Stylish East Hampton Village Retreat- Heated Pool and Sauna, Steps to Village
Long Island > Hamptons > East Hampton
House, Bedroom(s): 3, Sleeps: 6
Experience tranquility & convenience in the heart of East Hampton Village. Take morning strolls to cafes & boutiques. Return home to relax by the pristene pool.
$700 - $2,375 /Night
Glorious Sunset Strolls & Poolside Perfection Await!
Long Island > Hamptons > East Hampton
House, Bedroom(s): 4, Sleeps: 8
4 bedrooms (2 ensuite), 3 full bathrooms, 1 half bath, sleeps 8, heated pool
$650 - $2,000 /Night
Pet Friendly, Charming Bay View Cottage Close to Shops and Restaurants
Long Island > Fire Island > Ocean Beach
Cottage, Bedroom(s): 2, Sleeps: 5
This cottage is perfectly located just one house off the Great South Bay & a 2-minute walk to Fine Seaside Restaurants, Markets & Shopping
$500 - $630 /Night
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 - ALL RENTALS ARE MINIMUM 14 DAYS
$339 - $1,399 /Night
East Hampton Designer Gem in Private Clearwater Beach Association with pool!
Long Island > Hamptons > East Hampton
House, Bedroom(s): 3, Sleeps: 8
Beautiful newly renovated home with a pool located in private Clearwater Beach!
$400 - $1,300 /Night
4 Bedroom Beach House with Hot Tub
Long Island > Fire Island > Ocean Bay Park
House, Bedroom(s): 4, Sleeps: 10
Home away from home family beach retreat.
$1,100 /Night
HAMPTONS RETREAT *POOL & HOT TUB*
Long Island > Hamptons > East Quogue
House, Bedroom(s): 3, Sleeps: 7
3 bedrooms, 2 full bathrooms, sleeps 7
$600 - $800 /Night
Waterfront Family Friendly 6 Bedroom 4 Bath Pool & Hot Tub FREE EV CHARGING
Long Island > Hamptons > Westhampton
House, Bedroom(s): 6, Sleeps: 14
Large Well Maintained Spacious Home W/ Pool & Hot Tub Great Reviews
$315 - $1,750 /Night
Blufftop Cottage | Sound Views + Screened Porch
Long Island > North Fork
Cottage, Bedroom(s): 2, Sleeps: 4
Two-bedroom cottage on a Long Island Sound bluff in Baiting Hollow with panoramic water views and private beach access via stairs.
$143 - $18,700 /Night
Ocean Beach House - Fire Island, NY
Long Island > Fire Island > Ocean Bay Park
House, Bedroom(s): 3, Sleeps: 8
Beach House Contemporary 3 bedroom 2 bath, outdoor shower. Located between the Great South Bay and Atlantic Ocean (1) min to either Ocean or Bay.
$600 - $995 /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
Secluded, great bay views, great for families, close friends
Long Island > Fire Island > Kismet
House, Bedroom(s): 5, Sleeps: 12
We are now renting for 2026 in beautiful Kismet. 10% discount available on peak rentals
$490 - $1,835 /Night
Renovated North Fork Waterfront Home with Pool
Long Island > North Fork > Mattituck
House, Bedroom(s): 5, Sleeps: 12
4 Bedroom 3 Bathroom Waterfront Home w/ Pool - 14 DAY MINIMUM
$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 - $3,000 /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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