Holiday houses 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.

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Guest favourite
A bright living room area features a sectional sofa and a coffee table set on light carpet. A smart TV is positioned on a low stand, and natural light enters through a skylight. Decorative curtains frame the window, adding a touch of style.
Apartment in Medford
4.88 out of 5 average rating, 170 reviews

Cozy Apartment with King Bed - Separate Entrance

Enjoy your stay in this private, clean and comfy environment. Space offers a bedroom with a king size bed and a desk for at-home work. Living room includes a smart TV and a sectional. Unleash your inner chef! Access to kitchen utensils, dinnerware, and pots/pans. Free parking on premises. Convenient location with many necessities nearby (mall/gas station/restaurants). We are located 2 mins from I-495 and 15 mins from Macarthur airport. Great for visiting family in Port Jefferson, Patchogue, etc!

Guest favourite
Guesthouse in Valley Stream
4.92 out of 5 average rating, 49 reviews

GuesTiny Suite 30 min 》 NYC - 15 min 》JFK

Its coziness will make you feel at home the second you step in. This cute ground floor 280 sq ft Tiny Guest Suite is Fully furnished and nicely decorated - it comes with anything you can possibly imagine. It consist of 1 bedroom 1 bathroom & a kitchen/dining/living room area Rooms' sizes: Bedroom: 10ft x 7 1/2ft LR kitchen DR area: 19ft x 10ft Bath: 40" x 80" Given how close it is from everything - It is perfect for guests who plan on commuting to the city by train or move around by Uber.

Guest favourite
The entrance features a light-colored door with a modern handle, framed by a window to the side. Steps made of gray composite material lead up to the door, bordered by white railings providing a clean and welcoming entryway.
Apartment in Central Islip
4.97 out of 5 average rating, 125 reviews

Cozy studio w/ private entrance

Perfect for solo travelers or couples.This new, cozy studio is part of a larger home but fully self-contained w/ its own entrance. Inside, you’ll find: - A comfy living area with a pull-out twin bed and seating - A kitchen with essentials for light cooking - A private bathroom with shower, towels, and toiletries - High-speed Wi-Fi and a flat-screen TV Though attached to our home, your space is private. Located in a quiet neighborhood, close to attractions, restaurants, and transportation.

Top Guest favourite
A well-appointed sleeping area features a queen bed with crisp white linens, flanked by two illuminated nightstands. Above the bed, an abstract art piece adds a pop of color to the neutral walls. A small plant is positioned near the bed, enhancing the calming atmosphere.
Place to stay in Coram
4.99 out of 5 average rating, 127 reviews

T&T Unique Space

NEW ! Private renovated studio attached to a single family home. Private entrance queen bed w/full bathroom, sofa, 55”smartTV, kitchenette(no stove)free street parking in front of house.This is a drug free, non-smoking, no pets and no party unit. Minutes from Port Jefferson pier, LIRR, Connecticut Ferry, 15 min. to Mac Arthur airport. Shopping in Riverhead at Tanger Outlets a few exits from the LIE. 10min. to John T Mather Hospital & St Charles Hosp. Near Jakes 58 Casino and Top Golf.

Guest favourite
A cozy living area features a beige leather sofa with a decorative pillow, paired with a plush armchair. A wooden coffee table sits on a patterned rug, while a small plant adds a touch of greenery. Light walls and a wall sign contribute to a relaxed atmosphere.
Apartment in Rocky Point
4.75 out of 5 average rating, 220 reviews

Juniper Hollow

You are just a stone’s throw from the beach in this two-guest suit. Beach key provided! This indoor space measures 400 sf but you’ll find it well laid out with twice as much private outdoor space (for you warmer weather travelers). Older reviews are from 4 years ago and pre renovation, we are refreshed. Feel free to roam the rest of the 1/3 acre property of rolling hills, old growth trees, a hammock house, tree swings on the hill, and water views from the driveway.

Top Guest favourite
The exterior of a two-story house is illuminated softly in the evening, surrounded by tall trees. A porch with railings is visible, and a gravel driveway leads up to the entrance. The ambiance is serene, showcasing the natural woodland setting.
Apartment in Calverton
4.93 out of 5 average rating, 132 reviews

J&J's BnB Lovely, BR/Bath w/ Private Entrance!

Welcome to Jeanette and Jims Airbnb! We are avid travelers and look forward to hosting you on your trip to beautiful Long Island! Lovely, clean updated private room with private separate entrance and bathroom. Great location on a quiet wooded acre. 2 miles from Splish Splash. 3.6 miles from the Long Island Aquarium. 8.7 miles from Cupsogue Beach. 4.8 miles from Baiting Hollow Farm Vineyard. So much to do near by. Head easily to the north or south fork!

Top Guest favourite
Home in Milford
4.98 out of 5 average rating, 87 reviews

Luxe Beach House / 3 Bd-King / Chef Kitchen / 4 TV

***Monthly rental available Oct 1, 2025–May 31, 2026*** Enjoy a private waterfront oasis with breathtaking views from every room. Watch sunsets from the deck or walk 100 yds to the beach. Nature lovers will love the nearby Coastal Center. Entertain in the chef’s kitchen with gas range, breakfast bar, wine bar & pantry. Wake up to stunning vistas from the king master suite. With workspace & laundry room, this home is the perfect waterfront escape!

Top Guest favourite
Cottage in Patchogue
4.95 out of 5 average rating, 262 reviews

Quaint Cottage on Long Island's South Shore.

The Cottage is a lovely space enclosed in hedges for privacy on a one acre property. I do have 3 dogs, they are kept in a separate gated area on the property. The cottage is located 3 miles from downtown Patchogue which is enjoying a renaissance. There are many restaurants and cultural activities as well as ferry access to Fire Island (Davis Park) in the warmer weather. We are also the "Gateway" to The Hamptons.

Top Guest favourite
Apartment in Huntington Station
4.9 out of 5 average rating, 128 reviews

Clean Cozy Studio with Private Entrance.

Comfortable Safe Studio With Private Keypad Entrance in Huntington Area. Premium CABLE TV and All Amenities described are Included. There is Keurig coffee maker with cream and sugar so you can enjoy it. Cozy studio also has a toaster, microwave, refrigerator, own bathroom and small kitchenette that you can enjoy your own meals. You have a comfy King size Bed.

Top Guest favourite
Apartment in Rocky Point
5 out of 5 average rating, 8 reviews

Rustic Log Cabin, Long Island Vineyards

Escape to this 1930s Long Island log cabin-cathedral ceilings in the bedroom and living room, gas fireplace glowing, vintage furniture with a fresh twist. Full kitchen, twin beds for kids, all near vineyards and that suburban-but-country feel. Tucked in the suburbs, this cabin feels worlds away-like hiding in plain sight. Perfect for a quiet getaway.

Top Guest favourite
Guest suite in Ronkonkoma
4.95 out of 5 average rating, 150 reviews

Charming “hotel inspired” Retreat

Relax and recharge at this peaceful, centrally located retreat. Your private room features a cozy full-size bed, desk and chair for work or study, TV for entertainment, and a coffee station with microwave and mini fridge for quick bites. Enjoy the privacy of your own bathroom and entrance, with easy on-street parking right in front of the house.

Guest favourite
A solar-heated pool is featured in the foreground, surrounded by a stone patio. A modern residence is visible in the background, adorned with lush landscaping and outdoor seating areas. Evening lighting creates a welcoming ambiance, while trees frame the serene scene.
Home in Southampton
4.98 out of 5 average rating, 201 reviews

Dream Home with a wonderful heated pool in SH

Situated on a half-acre of land, this designer, updated, modern residence offers a peaceful and quiet Hamptons getaway. 4 wonderful bedrooms 3 modern bathrooms and a solar heated pool with mature landscaping offers a relaxing escape. Please read the additional disclosures, guidelines, and rules. No events, no parties, no smoking –

Popular amenities for Long Island holiday rentals

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.

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