
Holiday houses in Long Island
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Top-rated holiday rentals in Long Island
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Luxurious Waterfront Beach House On The Bay
Relax and enjoy your time at this beautiful east end waterfront getaway. This house is located right on the relaxing and exclusive Great South Bay with private beach... The experience will bring you the feel of tranquility everyone desires with vacationing out east. While offering all the enjoyments the island has at your fingertips. Centrally located to all island destinations. 90 minutes from Manhattan - 15 minutes to West Hampton - 15 minutes to Fire Island Ferrys. Visit top winery’s WiFi

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!

Romantic, Cozy and Private, 1 Block from Beach
Relax in your private romantic retreat with Canopy Queen Bed & Beautiful modern bathroom, 1 Block from beach, Second floor studio with small fridge, microwave, coffee maker, induction cook top, SmartTV... Just 7 min from the Long Island Railroad, Oyster Bay stop. Near to restaurants, shops, tennis courts. You can go biking, swimming, fishing, play golf, rent kayaks, motor boats, paddle boards. Visit Arboretums, Historic sites, Parks, walk along the water, go to the nearby movies and more...

Tranquility Getaway, Private Luxe Suite & Backyard
🌿 Welcome to Tranquility Getaway — a luxurious retreat nestled in the heart of Smithtown. Indulge in our Modern Newly Designed 2-bedroom Private Basement Luxe Suite, located on the left side of the property with a short staircase leading to your exclusive entrance on the lower level. Unwind in your private outdoor haven, featuring refined seating for four, a stone-top fire pit, and a solar-lit umbrella. THIS IS NOT THE ENTIRE HOUSE‼️ PLEASE REVIEW 📸 PHOTOS & HOUSE RULES BEFORE BOOKING‼️

Modern farmhouse w/ pool, beach, horses and winery
A new, modernized farmhouse with a heated saltwater pool in the heart of North Fork. Nestled on an acre of lush, fully fenced yard, the home can easily accommodate up to 8 guests and all pets! Minutes away from Love Lane (Mattituck's charming downtown), Breakwater Beach (one of best beaches in North Fork), Mattituck train station and surrounding the award winning Bridge Lane Vineyards and picturesque Seabrook Horse Farm, this bucolic home offers the perfect setting for a North Fork getaway.

Charming 2 Bedroom apartment
Enjoy our charming 2 Bedroom apartment that is in a quiet and friendly neighborhood in a cul-de-sac. Private entrance on first floor of our house with 2 Bedrooms, 1 Bathroom, Living room, Dining area, and a Kitchen. Close to: Main highways (Sunrise HWY/Long Island Expressway), Grocery stores, Winery & Vineyards, Davis park ferry, Downtown Patchogue village (Restaurants, bars, breweries, shopping), Beaches, Top Golf, MacArthur airport, Long Island Community Hospital, St Joseph’s College.

Savor Ocean Sunsets at a Soothing Beachfront Haven
Newly renovated and featured as a top Airbnb by New York Magazine, The Beach Cottage has been designed and decorated in a modern organic style, with a palette of whites and neutrals to create a serene and peaceful escape. Relax in the airy, light and open living room, which features a wall of glass for indoor/outdoor living with expansive, uninterrupted water views. Stay on the property for swimming, beach walks, sunsets and BBQs - or venture out to enjoy all the North Fork has to offer.

Joyful Beach House, viewing The Great South Bay
Amazing Great South Bay view with access to Shorefront and Rider Parks. This Ranch has an unobstructed view of the Shorefront Band Shell. Watch concerts and sunsets from the comfort of your patio. Walk down to the Patchogue Beach Club and enjoy the pool and beach. This open-concept home has 2 bedrooms, one bath, a remodeled bathroom, and a kitchen. The kitchen has stainless steel appliances, a farm sink, and a butcher block countertop with natural lighting that will brighten the home.

Quiet Waterfront Entire Apartment
Nestled in South Freeport, this 1 Br apt brings it all within your reach. Whether you are hoping to relax/work while drinking coffee on the patio or living room over looking the water, this is a very quiet and relaxing place to be. 5 minutes from the famous Nautical Mile where you can enjoy different restaurants, boat rides and other activities, minutes away from Southern State and Meadowbrook Pkwy, 15 minutes away from Jones Beach. Near different universities. AC in bedroom as well

Hudson River Peaceful Getaway, Explore from here
Self Check-In/Private Entrance. House trained Dogs and declawed Cats are Welcome (No additional pet fee). Driveway Parking for two cars. Peaceful, private flat on the Hudson River. Train to NYC (Scarborough Station) 10 min walk through historic neighborhood. Arcadian Mall (Grocery Store, Starbucks, etc) 7 min walk. Lots to explore in the area. Panoramic Rivers views from inside and out. Two televisions. Coffee/Condiments/Cooking Essentials provided. $25 cleaning with or without pets.

Boho Beach House
🌊WALK TO EVERYTHING🍹WELCOME TO THE WEST END STATE STREETS. This Boho inspired beach house is located in the heart of Long Beach, NY surrounded by restaurants, shopping and nightlife. Conveniently located only 2 blocks and a short walk to the beach, this newly renovated, fully furnished home includes garage parking, and all necessary living amenities to make for an easy summer living experience. ⛱️BEACH PASSES INCLUDED DURING SUMMER MONTHS (value of $120/day for 6 guests).

2 Bed 1 Bath Suite Washer/Dryer - Mid-Term Rental
Enjoy a few days away with your family & friends here in Long Island, New York. Just 40 minutes out from New York City. Freeport, Long Island is located just 40 mins east of NYC. Enjoy the excitement of city life, with the peaceful pace of this working class suburb. Property is close to the LIRR train into Manhattan. Travel by car, bus, or train. Your stay is just- 20 mins away from Queens, NY 35 mins away from Brooklyn, NY 40 mins away from Manhattan, NY
Popular amenities for Long Island holiday rentals
Other great holiday rentals in Long Island

Sag Harbor 3 bedrooms with Pool

Mastic Beach Surf House

Hamptons Waterfront Suite | Private Hot Tub

Stunning Guest Suite in Medford

Cabin in the trees

Cozy Private Entry 1 bedroom apt w/self check-in

WHITE SANDS Beach front modern 1 BR

Peaceful Bright Country House
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
- Plainview Holiday rentals
- New York City Holiday rentals
- Tuckahoe Holiday rentals
- Boston Holiday rentals
- East River Holiday rentals
- Washington Holiday rentals
- Hudson Valley Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Pocono Mountains Holiday rentals
- The Hamptons Holiday rentals
- Boat rentals Long Island
- Family-friendly rentals Long Island
- Fitness-friendly rentals Long Island
- Serviced apartment rentals Long Island
- Luxury rentals Long Island
- Rentals with a hot tub Long Island
- Cottage rentals Long Island
- Rentals with lake access Long Island
- Tiny house rentals Long Island
- Bungalow rentals Long Island
- Bed and breakfasts Long Island
- Beachfront rentals Long Island
- Boutique hotels Long Island
- Rentals with outdoor seating Long Island
- Apartment rentals Long Island
- Rentals with an EV charger Long Island
- Loft rentals Long Island
- Ski-in/ski-out rentals Long Island
- Villa rentals Long Island
- Rentals with pools Long Island
- RV rentals Long Island
- Holiday home rentals Long Island
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- Private suite rentals Long Island
- Rentals with breakfast Long Island
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- Rentals with a washing machine and dryer Long Island
- Rentals with a home theatre Long Island
- Rentals with an accessible height bed Long Island
- Aparthotel rentals Long Island
- Chalet rentals Long Island
- Cabin rentals Long Island
- Guesthouse rentals Long Island
- Rentals with a fireplace Long Island
- Rentals with a kayak Long Island
- Pet-friendly rentals Long Island
- Hostel rentals Long Island
- Rentals with an accessible height toilet Long Island
- Waterfront rentals Long Island
- Smoking-friendly rentals Long Island
- Townhouse rentals Long Island
- Farmstay rentals Long Island
- Rentals with a fire pit Long Island
- Rentals with a patio Long Island
- Rentals with a sauna Long Island
- Hotel rooms Long Island
- Tent rentals Long Island
- Beach house rentals Long Island
- Rentals with beach access Long Island
- House rentals Long Island
- Times Square
- Rockefeller Center
- Madison Square Garden
- Bryant Park
- Brooklyn Bridge
- Columbia University
- Central Park Zoo
- MetLife Stadium
- Yale University
- Bronx Zoo
- Old Glory Park
- Grand Central Terminal
- Ohel Chabad-Lubavitch
- Yankee Stadium
- United Nations Headquarters
- Jones Beach
- Chabad Lubavitch World Headquarters
- Empire State Building
- Citi Field
- Statue of Liberty
- Radio City Music Hall
- Fairfield Beach
- Cooper's Beach, Southampton
- USTA Billie Jean King National Tennis Center
- Things to do Long Island
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- Nature and outdoors Long Island
- Food and drink Long Island
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- Things to do New York
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- Things to do United States
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