
Vacation rentals in Long Island
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Top-rated vacation rentals in Long Island
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Vacation rentals for every style
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Popular amenities for Long Island vacation rentals
Long Island house rentals

Designer Home w/ Heated, Salt-Water Pool

Harborfront Star

Mastic Beach Surf House

Spectacular Lake Views from Every Room & Garden

Modern 3 Bd Spacious Apartment in PRIME Location

The Stella ~ Bellport Beach & Wetlands

Hamptons Oceanfront Oasis

Port Jefferson Convenient, Cozy and Chic!
Vacation rentals with pools in Long Island

Coastal Villa Suite pool•sauna•gym•theater•beach

Private Oasis W/Stunning Vinyard and Pool Views

4 BD w/ Heated Pool in E Hampton, Fully Furnished

Luxury cottage by the sea with hot tub and pool

Peaceful Retreat in Immaculate Architect’s House

Stylish+Modern Cape w/Saltwater Pool-5min to Beach

Midcentury Modern ZenHouse Sculptor Studio

Montauk Oceanview with Fireplace (2)
House rentals with pools in Long Island

Beach Barn w/ Heated Pool & Sauna - Dog Friendly

Spectacular Southampton Retreat!

Bellport Home: Pool, Hot Tub & Ping-Pong Oasis

Luxury Hamptons Poolside Paradise w/ Outdoor Sauna

GoodVibezHouse1.0~Pool~HotTub~GameRm~MiniGolf! 1BR

1800 Historical EH Home, 1 Mile to Town, Hot Tub!

South Bay Holiday

Southampton Charmer, 5 bedrooms w pool - Location
Your guide to Long Island
Welcome to Long Island
To the east of New York City, Long Island stretches from just past John F. Kennedy International Airport all the way to Montauk, and has a personality all of its own. At its heart, it’s a comfortable suburb so many New Yorkers call home, but it’s just as vibrant of a destination, especially thanks to its 118 miles of white-sand coastline with 150 beaches on both sides. It also has its own wineries and breweries, more than 60 golf courses, art and science museums, historic landmarks, and the fanciest of mansions along its Gold Coast. And with fresh seafood and farms of every kind, the food scene is just as thrilling.
The best time to stay in a vacation rental in Long Island
The warmest months in Long Island are from May to September, and the coldest are between December and February. While it does snow during the winter months, it tends to be less than the rest of the state — usually just a few snowstorms a year, and most times, it’s less than an inch. Annual events include the oldest Triple Crown race, the Belmont Stakes, in Elmont in June; the Tomato Festival in Mattituck in August; the Long Island Summer Festival at Smith Haven Mall in Lake Grove in July; and the Festival of Trees at the Cradle of Aviation Museum in Garden City during the holidays.
Top things to do in Long Island
Fire Island
No cars are allowed on this 32-mile-long barrier island along the Atlantic coast, inherently making it an idyllic beach destination where the pace of life slows down. Along with its 17 separate communities is the 40-acre maritime Sunken Forest and 168-foot-tall Fire Island Lighthouse — the tallest on Long Island.
Gold Coast Mansions
All that glitters just might be gold here. On the northern side of Long Island from Port Washington to Centerport, the coastline is dotted with mansions so extravagant that they’ve inspired literature. Highlights include the Vanderbilt Museum and Planetarium in Centerport.
Montauk Point State Park
At the far eastern point of the South Fork, the waters of the Atlantic Ocean meet the strait of the Block Island Sound, causing a phenomenon where the tides seem to race against one another. Take a hike along the shore and you might also see seals out on the rocks, or grab a board and surf the waves (surf fishing is also popular here). For a higher perspective, stop by the state’s oldest lighthouse, Montauk Lighthouse, right next door.
Destinations to explore
- Plainview Vacation rentals
- New York Vacation rentals
- Boston Vacation rentals
- Washington Vacation rentals
- East River Vacation rentals
- Hudson Valley Vacation rentals
- Philadelphia Vacation rentals
- Mount Pocono Vacation rentals
- Jersey Shore Vacation rentals
- Ocean City Vacation rentals
- The Hamptons Vacation rentals
- South Jersey Vacation rentals
- Rentals with a fireplace Long Island
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- Times Square
- Rockefeller Center
- Bryant Park
- Madison Square Garden
- Empire State Building
- Columbia University
- MetLife Stadium
- Yale University
- Jones Beach
- Central Park Zoo
- Yankee Stadium
- Citi Field
- Fairfield Beach
- United Nations Headquarters
- Southampton Beach
- Rye Beach
- Cooper's Beach, Southampton
- Grand Central Terminal
- Statue of Liberty
- USTA Billie Jean King National Tennis Center
- Radio City Music Hall
- Canarsie Beach
- Gilgo Beach
- The Metropolitan Museum of Art
- Things to do Long Island
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- Things to do New York
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