
Holiday rentals in Long Island
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Top-rated holiday rentals in Long Island
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Hamptons Oceanfront Oasis
Escape the hustle & bustle of city life and unwind at this stunning home in the Hamptons. The oceanfront oasis is the perfect way to wake up to ocean views, beaches and nearby restaurants. Relax on our spacious deck - perfect for morning coffees & sunset cocktails. It is just a short drive to the train station & only 15 minutes from the airport for quick getaways. For your safety, the home is equipped with Ring cameras and one-use key codes. Book now and experience the ultimate Hamptons escape!

A-Frame cabin with private beach & epic sunsets
Just a 1.5 hour drive from NYC, this home is the perfect beach getaway spot, with a few steps from the deck to the private beach with its beautiful view across the Great South Bay. Remote work with stunning water views through the wall of windows & in cold weather light a fire while sunlight floods the living space. Two queen bedrooms & bunk bed room sleeps 6 guests, great for families or a small gathering of friends. 5 min drive to ocean beach with great swimming & surfing at Smith Point.

Luxury Cottage with Spectacular Lake Views
Ultra Chic 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. 1 BR, 1 Bath, play/office/common room. Huge wrap around fenced in deck with Mid century modern fireplace allows for scenic dining, lounging and around the fire gatherings. #LakeViewCottage_GWL Town of Warwick Short Term Rental Permit #P25-0245

Waterfront next to Bellport
Enjoy stunning direct waterfront views of the Great South Bay from this newly renovated 3,200 sqf house. Swim off the back of your yard or at the property pool and at a private beach. Water views full and/or partial from every bedroom in the house. Three houses away from Bellport golf course and a short drive (1.5 miles) to Bellport downtown with small shops, cafes and restaurants. The water and the property are separated by a bulwark. Observe beautiful swans near the property daily.

Waterfront Round House View
A unique little beach house on the south shore of long island with the most beautiful view. The house is located on a canal. Dock is available! **We have Paddle Boards, Surf Boards and 3- 2 person Kayaks onsite for you to use during your stay. You can get to the Great South Bay by paddling to the mouth of the canal. And you can get to Fire Island by hiring a Water Taxi to pick you up! The octagon house was built in the 1970s. It's recently been refreshed with all new beds & linens.

Panoramic Lakeviews & Garden Oasis
Our property boasts unparalleled views of Greenwood Lake and the mountains beyond. Our lush private garden features hundreds of flowers and plants along with a seasonal waterfall cascading into a lily pond with fish and frogs. A shaded patio offers panoramic views and a gas grill. In winter, after skiing at nearby slopes, unwind in the claw foot tub or retreat to the cozy living room, with exposed wooden ceilings, a welcoming fireplace, a smart TV, a record player and board games.

The River Loft
Escape to The River Loft, a private riverfront retreat in Weston, CT. Built in 2015 by a visionary local architect, The River Loft open-air design seamlessly integrates the outdoors with the interior space. As you step inside this 750 sf small home, you'll be instantly captivated by the layout that makes it feel spacious. Sitting on over 2 acres of forested land with private river access. Book now for an unforgettable experience. For more images & videos visit insta @the.riverloft

Summer Sale! CozyCottage/Pet-friendly/ WalktoBeach
Inspired by my Dad's wanderlust and love of sea & sand. Relax and unwind in this completely remodeled, stylish Cottage a block and a half from Long Island Sound and .9 mile to Walnut Beach - walk to coffee, pizza, lobster shack! We offer a modern kitchen, breakfast nook, dining area, natural stone wall, parking and W/D. Located in a charming coastal town - enjoy quiet neighborhood walks, coastal trails, boardwalk, breweries and restaurants. 15 min to Yale/New Haven, 65 mi to NYC.

The Harbor House: Beachfront Home 1 hour from NYC
FEATURED #1 on Refinery29's "11 Best Beach Houses Near NYC" Welcome to Long Island’s iconic Gold Coast! Wake up to sweeping waterfront views and, if you’re lucky, catch a glimpse of our local bald eagle family soaring overhead! Explore nearby gems like the Vanderbilt Mansion & Planetarium, Caumsett State Historic Park Preserve, Del Vino Vineyards, and the lively Paramount Theatre. Stroll through Downtown Huntington or Northport Village for boutique shopping, great restaurants.

Sunny & Spacious Long Beach Retreat!
This is the perfect beach getaway! Open layout with windows, sunlight and comfort in every room from the den to the bedrooms to the backyard. Read book in a cozy chair, watch a movie in the den or play games and bbq outside. You can ride bikes or walk to the beach (passes included) or stay in and unwind on a spacious, relaxing hammock. Anything you need for your summer home is here. Walking/biking distance to beach and loads of restaurants, bars, etc nearby!

Luxury Lakefront w/ Beach, Dock & Kayak • 1h NYC
Escape to our modern, year-round lakeside paradise on Greenwood Lake, just 1 hour from NYC. This bright, airy home offers stunning lake views, a private dock, and a sandy beach area. Perfect for families or couples, enjoy seasonal activities from swimming and kayaking in the summer to skiing just 10 minutes away in the winter. Relax by one of two fireplaces or on the spacious deck. A tranquil retreat for relaxation and adventure. Permit N. 23-225

The Katalpa House -by the beach
-Our beach is private, key and beach tag provided- (in brown shed) This 1000+ sf home, features a newly renovated kitchen, outdoor shower, and many quirks that come with a 90 year old home. The furnishings are eclectic and vintage. Most of the flooring is also new. The beach and bluffs are only about a 2 minute walk. The 1/4 acre lot is shared with a secondary unit as you can see in the photos which is occupied by my sister.
Popular amenities for Long Island holiday rentals
Other great holiday rentals in Long Island

Luxe|Pool|BeachCar|Games|Movie|HotTub|Firepit

Best View + Putting Green + Private Beach

Stunning Guest Suite in Medford

Toes in the Sand Beach Cottage

Cozy, Chic, Fireplace Studio Getaway Certified!

Beautiful Waterfront Cottage

Cozy Riverfront Cottage•Pool•Hot Tub•35 min NYC

Rustic Log Cabin, Long Island Vineyards
Frequently Asked Questions
Where is Long Island located?
Long Island is situated in southeastern New York State, stretching east from New York City into the Atlantic Ocean. The area includes lively communities, coastal towns, and scenic beaches.
When is the best time to visit Long Island?
Late spring through early fall is often recommended for outdoor activities, as temperatures range from around 51–83°F (10–28°C) and rainfall is moderate. Visitors find the area inviting for beach outings, festivals, and exploring parks during these months.
What are some things to do near Long Island?
Long Island has sandy beaches, art galleries, vineyards, and historic estates to explore. Guests often enjoy walking along boardwalks, touring lighthouse sites, and sampling fresh seafood at locally rooted restaurants.
How is the weather near Long Island?
Long Island experiences cold winters, with January averaging 25–39°F (-4–4°C), and warm summers, reaching 67–83°F (20–28°C) in July. Rain falls throughout the year, so packing layers and a rain jacket is suggested.
Destinations to explore
- New York City Holiday rentals
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- Boston Holiday rentals
- Ocean City Holiday rentals
- Newark Holiday rentals
- Jersey City Holiday rentals
- Baltimore Holiday rentals
- Portland Holiday rentals
- Providence Holiday rentals
- Atlantic City Holiday rentals
- Newport Holiday rentals
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- Times Square
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