Long Island vacation rentals

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Top-rated vacation rentals in Long Island

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Guest favorite

Home in Levittown

4.83 out of 5 average rating, 24 reviews

Romance Vacation Sweet Home

Brand New Renovation by the Arquitech John Stumpf from Long Island ,that took my design to an amazing level of luxury tranquility and the most trendy space That you can only dream off. Have 3 bedrooms and 2 bathrooms Exquisite kitchen, stunning first floor and second floor, loft work area for people that need to work remotely and amazing large backyard for whoever wants to feel the fresh air the warmth of beautiful fireplace with nice hot cocoa or great glass of wine Free parking,Grill ,

Guest favorite

Home in Mastic

4.88 out of 5 average rating, 99 reviews

Cozy home. Comfy living

The whole group will enjoy easy access to everything from this centrally located home. three comfortable bedroom and two bathrooms with a large living room, dining and kitchen. close to the beach, nature reserved, kayaking, sky diving and Tanger outlet mall, restaurant and all the fast food located nearby. long island vast array of winery and farms stand etc. Guest is expected to follow house rules. Grace period of 15 mins after check is given after that fees will incur at the nightly rate.

Superhost

Home in West Haven

4.79 out of 5 average rating, 43 reviews

Beachside Retreat

***Brand new to Airbnb, the Beachside Retreat is perfect for a quick getaway or a longer short term stay. Gorgeously renovated home has 4 spacious bedrooms, living room & dining room large enough to entertain and kitchen perfect for making those home-away-from-home meals. Across the street from the beach, wake up to stunning sunrises with your morning coffee or relax on the wrap around porch and watch the sunset. With walking trails, restaurants and shops close by you never have to go far.

Guest favorite

Home in Northport

4.94 out of 5 average rating, 114 reviews

Cool pad, Private Rms, Walk to village, Wtr view

Beautiful pad on a tranquil street and walkable neighborhood. 5-10 minute walk to the village and 2-minute walk to the cliffs overlooking the bay and sound. Water view from one bedroom, great outdoor yard - very private. Updated amenities, marble bathroom, cozy indoor living area and very comfortable beds. The rental space is private and is the entire first floor of the home. The home is a two-story duplex with a shared entrance and private locking doors to each space. Wonderful location.

Guest favorite

Guest suite in Branford

4.9 out of 5 average rating, 100 reviews

Granite Bay Getaway - Private Studio Apartment

Enjoy Long Island Sound in this cozy getaway. Three block walk to shore. Quiet residential neighborhood. Private deck with lovely afternoon light. Private entrance. Fully equipped eat in kitchen. Picturesque shoreline town of Branford. Many wonderful restaurants, 2 within walking distance. Land trust hiking trails at end of street. Ten minutes to New Haven, Yale & Avelo airport. Train station 2 miles away with connections to New York City and Boston. ½ mile from CT Hospice.

Guest favorite

Home in Greenport

4.93 out of 5 average rating, 107 reviews

Maritime Village Getaway with Backyard

Well located Greenport 3 bedroom, 2 bath home. Historic renovated private home with modern furnishings and updated appliances and finishings. Patio and yard with outdoor shower, fire pit, and yard. Central AC and heat. Properly licensed as a rental with Greenport Village and Suffolk County. I now add the airbnb fees and local and state taxes onto the listing. If you have questions about this please reach out. Not sure how transparent the fee structure is for guests.

Superhost

Home in Westhampton Beach

5 out of 5 average rating, 4 reviews

Summer Main Home plus cottage close to Main Street

Come relax and enjoy! Beautifully updated Main home with separate cottage. Perfect for in-laws and guests. Each home has its own kitchen, living space, washer/dryer, and outdoor seating. Main house: 4 Br, 3 ba Cottage: 2 Br, 1 ba Outdoor shower for an after beach rinse, 2 patios, pergola, hammock, bbq. A two person kayak available for use; beach passes included. Games, internet, tv... Walk to coffee shops, restaurants, worship, and marina. Bike to beach.

Guest favorite

Cottage in Greenwood Lake

4.94 out of 5 average rating, 84 reviews

Cottage with Picturesque Views

Quaint Cottage set high above Greenwood Lake with Private beach and lake front community access. Minutes away from Mountain Creek Ski Resort, Spa & Water park, Mt. Peter Ski & Tubing, Warwick creameries, breweries & vineyards & apple picking. 2 BR, 1 Bath private 2 car parking. Fenced in deck allows for scenic dining. Fire pit with Adirondack seating allows for around the fire gatherings. #CozzyCottage_GWL Town of Warwick Short Term Rental Permit # 34234

Guest favorite

Houseboat in Riverhead

5 out of 5 average rating, 10 reviews

Peconic River Boatel

Perfectly updated nautical houseboat situated on the scenic Peconic River. Featuring two picturesque bedrooms, a full service eat-in kitchen and a living room with panoramic river view. Enjoy your morning coffee on the outside deck while taking in the sunrise. This historic waterfront town was named to Forbes Advisor’s “Best Places to Travel in 2023” — one of just 11 U.S. destinations on this year’s list. A must see for adventurers and families alike!

Guest favorite

Apartment in Long Beach

4.99 out of 5 average rating, 174 reviews

Incredible Long Beach Private Rental

True 5 star two bedroom rental. Newly renovated and professionally designed. Stunning ocean views from private second floor deck. You have your own barbecue and fully furnished outdoor space so you can enjoy the your stay on your terms. You are just a walk to the bars and restaurants of the West End. No car required! Walk or catch the bus from the train. Only 700 feet from the ocean. Due to allergies in the home we are unable to host any animals.

Superhost

Home in Shelter Island

4.9 out of 5 average rating, 115 reviews

Hay Beach Getaway!

Welcome to our family-friendly oasis just two blocks from beautiful beaches! Our house offers an open space living area, an expansive yard, fire pits, and a basement with a playroom and workout area. Enjoy our quiet neighborhood. We provide kid-friendly toys, beach gear, bicycles, and more. Sleeps six, with additional options available for larger parties. Cleaning fees for winter stays are 0$.

Guest favorite

Home in Montauk

4.91 out of 5 average rating, 46 reviews

Montauk Family Gem: HotTub, Pro Kitchen, Fireplace

Escape to your perfect Montauk getaway! Nestled on a secluded, beautifully landscaped lot at the end of a quiet dead-end street, this recently renovated 4-bedroom, 3.5-bathroom beach house offers the ultimate combination of luxury, comfort, and privacy. We are also pet friendly!

Popular amenities for Long Island vacation rentals

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.

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