
Holiday rentals in Long Island
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Top-rated holiday rentals in Long Island
Guests agree: these stays are highly rated for location, cleanliness and more.

Modern Southampton Cottage | Heated Pool & Peloton
Modern Hamptons cottage with mid-century modern interior, our 3 bedroom/ 2 bathroom cottage is set on manicured grounds and perfectly equipped for your stay. Heated gunite pool (summer months only) with retractable cover, Peloton bike and Central Air throughout. Newly renovated kitchen with high end appliances, large outdoor deck perfect for entertaining with new Weber grill. Private driveway accommodates 4 cars. 4 adult bicycles. 8 min ride to Southampton village. 15 min to Coopers Beach.

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!

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.

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.

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

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

Recharge at our Renovated ocean front unit
Looking for a relaxing weekend to recharge on the beach? Then this newly renovated, bohemian-chic, apartment is perfect for you. Imagine waking up every morning to beautiful unobstructed ocean views and ending your night with a drink in hand watching the sunset. If you’re lucky, you might see some whales or dolphins breaching in the water right off our private beach. We would love to host you for your Montauk beach getaway.

Captain's Cottage on Working Farm with Animals
Charming, fully renovated cottage with cathedral ceilings and private deck. Home has a separate queen bedroom, kitchen and living room on the main floor with small stove fireplace. There is a small loft on the 2nd floor with 2 twin beds accessed by a library ladder (note: no standing headroom in loft). Private outdoor deck with seating and BBQ. Fast wi-fi, laundry access and pet friendly.
Popular amenities for Long Island holiday rentals
Other great holiday rentals in Long Island

2000 sq foot Beach house apartment by the sea

Mastic Beach Surf House

Sag Harbor 3 bedrooms with Pool

Hamptons Waterfront Suite | Private Hot Tub

The Hamptons Surf Cottage!

Sea Level: Stylish studio 2 blocks to beach!

WHITE SANDS Beach front modern 1 BR

Waterfront Designer Retreat | Fire Pit & Sunsets
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
- Waterfront rentals Long Island
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- 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
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