Long Island Vacation Rentals

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
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
Wading River Beach Studio | Steps to Shore, Full Kitchen
Long Island > North Fork > Wading River
Cottage, Bedroom(s): 1, Sleeps: 2
Beach studio in Wading River, steps from the shore on Long Island Sound. Queen bed, pullout sofa sleeper, full kitchen with breakfast bar, and a full bathroom.
$92 - $233 /Night
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
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
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
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
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
Soundview Beach House | Deck, Kayaks & Beach
Long Island > North Fork > Wading River
House, Bedroom(s): 3, Sleeps: 8
3 Bedrooms, 2 Bath, Sleeps 8
$441 - $2,100 /Night
Hilltop Haven in Montauk, Family & Pet Friendly, Designer Digs, Walk to Ocean & Town
Long Island > Hamptons > Montauk
House, Bedroom(s): 4, Sleeps: 9
Renovated Modern Farmhouse with pool, Super Private, Family & Pet Friendly, Comfortable, Clean & Fully Stocked w/ All You Need!
$700 - $3,500 /Night
Grand North Fork Family Home
Long Island > North Fork > Peconic
House, Bedroom(s): 5, Sleeps: 10
Grand Beach Home, Room For Family and guests. 5 BR, 3.5 BA, Radiant Heat, Gourmet Kitchen With Wolf Stove. 10 Foot Ceilings, Salt Water Pool, Park-Like Grounds.
$1,150 - $1,575 /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
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 House with Private Beach Access - Rental Registry Cert #23-1,120
Long Island > Hamptons > Montauk
House, Bedroom(s): 5, Sleeps: 12
Beautiful, spacious five bedroom, three full bath in Culloden Shores with private beach access is the ideal family rental! Walk to beach and Montauk Harbor.
$600 - $1,050 /Night
Think Big Blue Skies, 4 Bedroom, 4 Bath Water Mill
Long Island > Hamptons > Southampton
House, Bedroom(s): 4, Sleeps: 8
This rental doesn't come on the market very often, as usually leases turn into long term leases.
$500 - $1,933.33 /Night
Waterfront Home w Private Beach & Firepit
Long Island > North Fork
House, Bedroom(s): 3, Sleeps: 6
3 bedrooms, 2.5 bathrooms, 6 sleeps

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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