Vacation rentals in Long Island

Long Island stretches east from Queens into the Atlantic, offering everything from Montauk surf to North Fork vineyards and Gold Coast mansions.

Best time to book

Memorial Day through Labor Day for beaches; fall for wine harvest and quieter inns.

Common rental types

Beach cottages · Hamptons estates · Vineyard guest houses · Soundfront homes

Getting there

Reach the Hamptons and North Fork by car via I-495/LIE; JFK and LaGuardia are the closest major airports.

Looking for bookable deals?

Our partner A1 Vacation Homes adds new special offers every week — see what's live across all destinations right now.

Representative homes based on the layouts Long Island visitors book most — use them to compare space, amenities, and nightly budget before you book.

Beach House

Montauk · Long Island

4 bd3 baSleeps 10

Ocean viewBeach accessHeated pool

from $890 / night

Guest Cottage

Greenport · Long Island

2 bd1 baSleeps 4

Vineyard viewsPatioFireplace

from $325 / night

Estate Guest House

East Hampton · Long Island

3 bd3 baSleeps 6

Private poolTennis court accessGated

from $750 / night

The Hamptons

East Hampton, Southampton, and Montauk — high-end beach living and surf culture.

North Fork

Wine country, farm stands, and relaxed waterfront villages like Greenport.

South Shore

Long Beach, Fire Island, and family-friendly Atlantic beaches.

North Shore

Gold Coast mansions, harbors, and easy access from New York City.

Neighborhoods, seasons, and booking tips — the full destination guide.