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 - ALL RENTALS ARE MINIMUM 14 DAYS
$339 - $1,399 /Night
Wading River Beach Cottage | Wetland Views, Steps to Shore
Long Island > North Fork > Wading River
House, Bedroom(s): 2, Sleeps: 4
Ideal for nature, this artist-designed home offers unparalleled access to the serene community bay beach of Wading River, where quiet beach days.
$430 - $890 /Night
Southampton 4BR | Pool, Game Room, Near Shinnecock
Long Island > Hamptons > Southampton
House, Bedroom(s): 4, Sleeps: 10
4 Bedrooms, 3.5 Baths, Sleeps 10
$500 - $2,500 /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
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 - $1,000 /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
Lagoon Lodge | Private Dock + Beach Access
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!
$276 - $1,756 /Night
Southampton 5BR · 4 Kings, Pool & Private Yard
Long Island > Hamptons > Southampton
House, Bedroom(s): 5, Sleeps: 10
5 Bedrooms, 3 Baths, Sleeps 12
$425 - $2,900 /Night
Lindsay Estate | Furnished Pool & Hot Tub
Long Island > North Fork > Wading River
Estate, Bedroom(s): 4, Sleeps: 9
A luxury North Fork retreat with a 40x16 heated saltwater pool, sun ledge, hot tub, and private backyard oasis. This 4-bedroom home sleeps up to 9
$385 - $1,600 /Night
Jamesport Cottage | Walk to Peconic Bay, Fire Pit
Long Island > North Fork > Jamesport
Cottage, Bedroom(s): 3, Sleeps: 8
Entire home in Jamesport, New York 8 guests 3 bedrooms 6 beds 2.5 baths
$404 - $863 /Night
4 bedroom 2.5 bathroom AC Decks Pvt Beach HotTubFirePit
Long Island > Hamptons > Montauk
House, Bedroom(s): 4, Sleeps: 8
Walk To Private Beach
$450 - $1,250 /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.
$450 - $975 /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.
$795 - $2,395 /Night
Beautiful Sag Harbour Village - Heated pool 5 min walk to BeachRestaurantMuseum
Long Island > Hamptons > Sag Harbor
House, Bedroom(s): 3, Sleeps: 6
Pristine 3-bedroom house with heated pool & central air. Short walk to bay beach
$2,000 - $2,500 /Night
5 min walk to Beach Restaurants Museums - Village House with large backyard
Long Island > Hamptons > Sag Harbor
House, Bedroom(s): 4, Sleeps: 8
Our Sag Harbor vacation rental is ONLY two minutes away from the beach!
$1,300 - $1,500 /Night
Water View Beach House just steps to Private Sandy Beach
Long Island > North Fork > Southold
House, Bedroom(s): 4, Sleeps: 8
Newly Renovated 4-Bedroom Ranch just steps away from a private Sandy Beach! Permit #630
$350 - $1,000 /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
Bahia Mar – Private Peconic Bayfront
Long Island > North Fork > Laurel
House, Bedroom(s): 3, Sleeps: 8
The Bahia Mar sits directly on a private beach overlooking the Peconic Bay and offers an idyllic escape for discerning guests, with meticulous design.
$762 - $1,594 /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

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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