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The best holiday rentals in Long Island

Check out our pick of great holiday rentals in Long Island

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Superb: 9+ Very good: 8+ Good: 7+ Pleasant: 6+
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Set in Hampton Bays in the New York region with Meschutt Beach nearby, Aria & Mare Hamptons offers accommodation with free private parking, as well as access to a hot tub. The property has sea views and is 27 km from Splish Splash and 43 km from Montauk Point Lighthouse. The loveliest stay!! We had the best time and are so thankful for all little touches and great recommendations.

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9.7
Exceptional
111 reviews
Price from
US$357.50
per night

Offering inner courtyard views, The 1708 House is an accommodation set in Southampton, 2.2 km from Gin Beach and 34 km from Montauk Point Lighthouse. This property offers access to a patio, a pool table, free private parking and free WiFi. The bed and breakfast offers garden views and a sun terrace. This property blew me away. The amenities and decor were top notch.

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9.7
Exceptional
165 reviews
Price from
US$345
per night

The Pines Men-Only Stay is a recently renovated homestay in Fire Island Pines, where guests can make the most of its outdoor swimming pool and terrace. A fitness room is available for guests, along with a solarium. The homestay has private entrance. Absolute gem in the Pines 🌊🔥 From the moment we arrived, this property delivered the kind of stay you hope for on Fire Island and rarely get all at once. The home is gorgeous—immaculately kept, stylish without trying too hard—and the heated pool became our daily ritual. Beds? Massive, cloud-level comfortable. We slept like babies after sunset boardwalk strolls. There’s also a proper gym on site, so we could offset all the “vacation decisions” we made at dinner. 😅 What really sets this place apart is the host. Warm, proactive, genuinely thoughtful—the kind of hospitality that feels effortless because it’s real. He even made me an iced coffee (I’m usually not a fan) that was so good I asked for the recipe. Communication was smooth end-to-end and check-in/check-out were a breeze. If you’re debating where to stay in the Pines, this is your sign. Beautiful property, heated pool, huge comfy beds, gym for the motivated—and a host who turns a great trip into an unforgettable one. We’ll be back. 🇿🇦❤️

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9.3
Superb
45 reviews

33 km from Splish Splash, Vine & Sand--Southold NY's Newest B&B is a recently renovated property located in Southold and provides air-conditioned rooms with free WiFi and private parking. Guests staying at this bed and breakfast have access to a patio. The bed and breakfast features an outdoor swimming pool with a fence, as well as a hot tub and luggage storage space. Very clean, updated B&B, very quaint and near vineyards, beach and town.

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9.2
Superb
5 reviews

Located in Glen Cove, 25 km from Belmont Park Race Track and 27 km from Citi Field, Glen Cove Vacation Rental Less Than 1 Mi to Downtown! offers air conditioning. The property is around 31 km from Arthur Ashe Stadium, 36 km from Bronx Zoo and 40 km from Yankee Stadium. Free WiFi is available throughout the property and Nassau Veterans Memorial Coliseum is 20 km away. Clean, well equipped, quiet. Excellent bedding. Very nice hosts.

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10
Exceptional
10 reviews
Price from
US$235
per night

Located in Bay Shore, 39 km from Jones Beach State Park and 39 km from Nikon Theater, Bay Shore Vacation Rental with Shared Yard! offers air conditioning. The Belmont Park Race Track is within 49 km of the apartment. Free WiFi is available throughout the property and Nassau Veterans Memorial Coliseum is 34 km away. There is no breakfast. But location is very good.

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9.8
Exceptional
7 reviews
Price from
US$283
per night

Featuring a spa bath, Cozy Dix Hills Apt with Deck about 7 Mi to Beach! is located in Dix Hills. Free WiFi is provided throughout the property and private parking is available on site. The property is non-smoking and is situated 28 km from Nassau Veterans Memorial Coliseum. The grounds are beautiful and the apartment was lovely- clean, comfortable, and well appointed. Everything we needed was there. Kelly greeted us and gave us great information about the area. She was delightful to visit with.

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9.8
Exceptional
9 reviews
Price from
US$236
per night

Set in Baiting Hollow, within 39 km of Agawam Park, Beach cottage villa offers accommodation with air conditioning. With free private parking, the property is 7.8 km from Splish Splash and 15 km from Long Island Railroad. The view was incredible. Access to the beach. Comfortable amenities and living space. Even deer came to visit to add to the view.

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9.1
Superb
15 reviews
Price from
US$240
per night

Come As You Are Inn LLC in Sayville provides adults-only accommodation with a seasonal outdoor swimming pool, a garden and a bar. A hot tub is available for guests. There is a sun terrace and guests can make use of free WiFi and free private parking. Out of all the accommodations I booked during my travels in the United States, this has been the most exceptional one. From the moment the door opened, I felt at home and really, really welcome. The landlords are amazing people, who will go out of their way to make their guest feel comfortable. I actually spent hours chatting with them instead of exploring the area, because they were just so interesting and easy to talk to. In addition to amazing conversation, I even got treated to a piano recital in the evening. So while Sayville may not be the most thrilling place you could think of, I would consider coming back just to stay at the "Come as you are Inn" again. Also, I suspect, it may be difficult to find another B&B with a great cook and a great pianist under the same roof. Breakfast was lovely, the bedroom and bathroom were great, there was not a thing to complain about in that house. I got offered lifts, I was allowed to do some laundry (mine, not theirs :)) - things that aren't for granted and which I very much appreciated. The B&B is within walking distance to the train station, if you don't have a car. It's also just a few minutes' walk to the Main Street with shops, cafés and restaurants. There's a big supermarket nearby. One could even walk to the ferry terminal to Fire Island within 20-40 minutes (depending on your pace). My stay at the "Come as you are Inn" has been an extraordinary experience and I'm very glad I stopped there.

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9.8
Exceptional
41 reviews
Price from
US$200
per night

Located in Greenport in the New York region, Bright Apartment - half Mi to Greenport Harbor! has a patio. Providing free WiFi throughout the property, the non-smoking apartment features a spa centre.

The air-conditioned apartment is composed of 1 separate bedroom, a fully equipped kitchen with a dishwasher and an oven, and 1 bathroom. Towels and bed linen are provided in the apartment. For added privacy, the accommodation features a private entrance. Location very good. Clean, updated, kitchen stocked if want to cook. Good size refrigerator. Local artist works on walls. Bed comfortable and each has own bedside table. Quiet location.

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9.8
Exceptional
14 reviews
Price from
US$283
per night

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