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
Sprawling Southampton home with pool & jacuzzi room for entire family
Long Island > Hamptons > Southampton
House, Bedroom(s): 4, Sleeps: 14
4 Bedrooms, 3.5 Baths, Sleeps 14
$500 - $2,500 /Night
BEAUTIFUL BEACH ESCAPE 10 MINS TO WEST H BEACH VILLAGE | New York
Long Island > Hamptons > East Moriches
House, Bedroom(s): 6, Sleeps: 8
Beautiful, private BEACH ESCAPE, 6 Bd, 5 baths, near West Hampton Beach Village
$795 - $13,000 /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
Cedar Beach House: Steps to Beach, Near Vineyards
Long Island > North Fork
House, Bedroom(s): 2, Sleeps: 6
The Beach Bungalow is a cute beach cottage getaway that is kept affordable for families looking to spend time in the heart of North Fork.
Walk to Breakwater Beach in Heart of Wine Country
Long Island > North Fork > Mattituck
House, Bedroom(s): 2, Sleeps: 6
Beaches, wineries, and Love Lane all just minutes away!
$495 - $995 /Night
The Lindsay Luxurious Estate: Heated Pool, Hot tub, Huge Yard
Long Island > North Fork > Wading River
Estate, Bedroom(s): 4, Sleeps: 9
This Large Luxurious home was purchased in 2021, and lots of work was done to make this the perfect summer getaway!
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 - $3,000 /Night
BEAUTIFUL, SERENE 7 miles to WEST-HAMPTON!
Long Island > Hamptons > East Moriches
House, Bedroom(s): 5, Sleeps: 10
Beautiful house and grounds, perfect for fun and serene!
$895 - $1,695 /Night
Historic Luxury Seaside Getaway
Long Island > North Fork > New Suffolk
House, Bedroom(s): 6, Sleeps: 16
This 1883 Historic Home is completely renovated & brilliantly decorated. Located in the heart of New Suffolk.
$550 - $2,395 /Night
Lagoon Lodge: North Fork,Charming 3Br, Waterfront, near Greenport, WIFI
Long Island > North Fork > East Marion
Lodge, Bedroom(s): 3, Sleeps: 8
Lagoon Lodge is a charming waterfront home with 3 bedrooms, and 2 bathrooms, and has central air and high-speed internet!
$362 - $1,756 /Night
Classic Southampton Home: 5BR, Pool,Jacuzzi, Cooper's Beach
Long Island > Hamptons > Southampton
House, Bedroom(s): 5, Sleeps: 10
5 Bedrooms, 3 Baths, Sleeps 12
$600 - $2,500 /Night
NEW LISTING - Newly Renovated Beach Home - Short Walk to Beach and Town
Long Island > Hamptons > Montauk
House, Bedroom(s): 4, Sleeps: 8
Newly renovated beach home near everything. Only a 5 min walk to the town and beach.
$590 - $1,350 /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
NEW HOUSE,6Bd,5Bth,4200sqft,Private Drive,Pool,Bikes,Games,Toys,Gigabit Internet
Long Island > Hamptons > Westhampton
House, Bedroom(s): 6, Sleeps: 12
6 bedroom, 4.5 bathroom, 4,200 sq ft cedar shingle home with high-end finishings, appliances and latest technology throughout.
$295 - $1,895 /Night
SIX BEDROOMS -HEATED POOL- POND- NEWLY RENOVATED: VERY PRIVATE. ONE WEEK MINIMUM RENTAL
Long Island > Hamptons > East Quogue
House, Bedroom(s): 6, Sleeps: 12
SIX Bedrooms: Four Bathrooms: Brand new POOL, POND AND GAZEBO with outdoor livingroom: Interior newly renovated and remodeled: Very private 2 acre get away
$1,285 - $1,785 /Night
Beach Bungalow: Nearby Beach, Yard w Firepit
Long Island > North Fork > Wading River
Cottage, Bedroom(s): 3, Sleeps: 6
The Beach Bungalow is a cute beach cottage getaway that's kept affordable for families looking to spend time on the North Fork.
4BR+ Newly Renovated Southold Home near Beaches and Vineyards
Long Island > North Fork > Southold
House, Bedroom(s): 4, Sleeps: 8
This is a newly renovated 4BR+ home in the heart of Southold, just minutes from beautiful beaches and vineyards. A beautiful spot for an escape from it all!
$350 - $600 /Night
Montauk Beach Bungalow West
Long Island > Hamptons > Montauk
Apartment, Bedroom(s): 2, Sleeps: 4
Relaxing beach bungalow that sleeps, 4 people.
$461 - $758 /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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