Discover a selection of 299 vacation rentals in Long Island that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and WiFi. Prices start at $153 per night, and houses and cottages are popular options for a stay in Long Island. Either way, you'll find a rental for everyone's needs.
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Top rated rentals — Long Island
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Destination guide

Discover peaceful Maine island living at its finest

Rocky coves and hidden inlet beaches dot the coast of this scenic island, nestled in the waters of Casco Bay off the coast of Portland. Lobster fishing is the way of life on Long Island, which seceded from Portland in 1993 and is now an independent year-round community (though the population drops from 1,000 to a mere 200 in the winter). Long Island vacation rentals offer car-free tranquility -- you can only get to the island by boat, but the laid-back island atmosphere makes the effort worth it.

Things to do

Everything from war history to wild rabbits on one island

While you're busy searching for singing beaches, you might stumble across a former army building or two, thanks to Long Island's role as a fueling depot for the U.S. Navy during WWII. To the delight of history buffs, many of the former supply stations are still standing along the coast today. Breathtaking views are in high supply, particularly at the Flat Rocks Scenic View at the island's northern tip. And just try not to smile as you watch the rabbits roam free along Harbor de Grace Street (affectionately called Bunny Hop for good reason).

Activities

Let the sand sing beneath your feet on Long Island's beaches

A healthy sense of adventure (and direction) will come in handy when you head to your Long Island vacation rental. The town and island are perfect for exploring on foot and even better by bike (but bring your own, as there's nowhere to rent one). You might get a little lost since there are no street signs, but that's a good thing, because most of the famous beaches are hidden and unmarked anyway. You'll know when you get there, though -- the locals swear that the smooth white sands "sing" beneath your toes as you walk.

Weather

Cool ocean waters - are you brave enough to take a dip?

The fresh coastal breezes and clean ocean air of Long Island are a real treat, but you'll want to leave the swimming to the daredevils of the bunch. The waters are cold year round, and downright frigid in the winter months, in particular December through February, when air temperatures might not even break the freezing mark. Most visitors stick to the warmer months of May to September, but only from June to August will the mercury even cross into the 70s. Pack layers when heading to your Long Island vacation rental so you're not left out in the cold.

Natural features

Beaches and bogs and beavers, oh my

Just 3 miles long and 1 mile wide, Long Island packs a huge variety of wildlife and nature into a tiny space. The coast varies between rocky coves, picturesque harbors, and white sand beaches, while the island's interior offers everything from mixed forests to freshwater marshes. Most development is clustered around the Town of Long Island on the island's south end. A 125-acre conservation area is home to hiking trails, a cranberry bog, and native beavers. And, of course, don't forget the frolicking bunnies.

How to get there

Transportation options to and around Long Island

Fly into Portland, ME (PWM-Portland Intl. Jetport), the closest airport, located 8.1 mi (13 km) from the city center. If you can't find a flight that works for your travel itinerary, you could also fly into Brunswick, ME (NHZ-Brunswick Executive), which is 18.3 mi (29.4 km) away.

How many vacation rentals are available around Long Island?

Our 2021 property listings offer a large selection of 299 vacation rentals around Long Island. From 182 house rentals to 55 cottage rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.