Long Island Vacation Rentals

Steve’s Place | Heated Pool Southold Retreat
Long Island > North Fork > Southold
House, Bedroom(s): 3, Sleeps: 6
Everything you would possibly need and want for a wonderful stay is here!
$431 - $1,019 /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
Chalet-by-the-Sea
Long Island > Fire Island > Kismet
House, Bedroom(s): 4, Sleeps: 8
House, 4 Bedrooms, 1.5 Baths, sleeps 8.
$500 - $1,000 /Night

OFFER $500.00 discount for 7 night minimum.

Special offer period: Jul 17, 2026 - Sep 6, 2026

Perfect Southampton Village Getaway
Long Island > Hamptons > Southampton
House, Bedroom(s): 3, Sleeps: 6
3 bedroom, 3 full bath
$550 - $645 /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
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
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
Scenic Gem: Waterfront View, Beach Access
Long Island > North Fork > Wading River
House, Bedroom(s): 3, Sleeps: 7
Scenic Gem is a peaceful Long Island North Fork retreat offering the perfect balance of comfort, luxury, and breathtaking year-round waterfront views.
$389 - $1,020 /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
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
One House from The Ocean - New Construction - Ocean Bay Park
Long Island > Fire Island > Ocean Bay Park
House, Bedroom(s): 4, Sleeps: 10
Come put your feet in the sand in our beautiful new home located steps from the beach.
$2,000 - $3,000 /Night
Entire home Sag Harbor 1.5 acre CAR and RESIDENT BEACH ACCESS
Long Island > Hamptons > Sag Harbor
House, Bedroom(s): 3, Sleeps: 6
Sag Harbor Private 1.5acre Oasis with access to all private resident beaches. Special Offer- July 27- Labor Day based on select dates and length of stay.
$1,150 - $1,850 /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
Nature’s Paradise | Private Dock & Water Views
Long Island > North Fork > Mattituck
House, Bedroom(s): 4, Sleeps: 9
Beautiful Long Island Sound Beach with incredible sunsets.
$450 - $1,545 /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
Peconic Sound Beach Cottage | Walk to Sound
Long Island > North Fork > Peconic
Cottage, Bedroom(s): 3, Sleeps: 7
3 bedrooms, 2 bathrooms, 7 sleeps
$287 - $1,443 /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
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

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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