Vacation Rentals in Long Island
Start comparing over 3,613 rentals in Long Island and book at the best price!
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Vacation rentals with pets allowed
Wading River, North Fork
9.3
Vacation rental for 2 people, with balcony, with pets
Free cancellation
from $184 per night
Fire Island, Suffolk County
8.6
Vacation rental for 4 people, with terrace
Free cancellation
from $554 per night
Suffolk County
9.5
Vacation rental for 6 people, with pool and yard as well as hot tub, with pets
Free cancellation
from $257 per night
Ocean Beach (NY), Suffolk County
7.4
Vacation rental for 3 people, with balcony
Free cancellation
from $586 per night
Vacation rentals in Long Island
Massapequa, Nassau County
9.9
Vacation rental for 2 people
Free cancellation
from $229 per night
Montauk, North Fork
9.8
Vacation rental for 4 people, with yard and sauna
from $355 per night
Long Beach (NY), Nassau County
9.7
Vacation rental for 2 people, with hot tub
Free cancellation
from $344 per night
Long Beach (NY), Nassau County
10.0
Vacation rental for 5 people, with balcony
Free cancellation
from $296 per night
Vacation rentals with sea view
Shelter Island Heights, North Fork
Vacation rental for 10 people, with yard
Free cancellation
from $657 per night
Southampton (NY), North Fork
Vacation rental for 10 people, with terrace and yard, with pets
Free cancellation
from $1,645 per night
Sag Harbor, North Fork
Vacation rental for 10 people, with yard and balcony, kid friendly
Free cancellation
from $105 per night
Southold, North Fork
Vacation rental for 9 people, with pool
Free cancellation
from $1,312 per night
Vacation rentals with free cancellation
Greenport, North Fork
9.8
Vacation rental for 2 people, with terrace
Free cancellation
from $321 per night
Bridgehampton, North Fork
10.0
Vacation rental for 2 people, with terrace and yard
Free cancellation
from $538 per night
Nassau County
9.5
Vacation rental for 2 people, with pool and balcony as well as yard
Free cancellation
from $188 per night
Elmont, Nassau County
10.0
Vacation rental for 2 people
Free cancellation
from $209 per night
Child-friendly vacation rentals
East Hampton, North Fork
9.4
Vacation rental for 7 people, with balcony and yard, kid friendly
Free cancellation
from $329 per night
Sag Harbor, North Fork
Vacation rental for 6 people, with yard and balcony, kid friendly
Free cancellation
from $716 per night
Northwest Harbor, North Fork
Vacation rental for 6 people, with balcony and yard, kid friendly
Free cancellation
from $314 per night
Springs, North Fork
Vacation rental for 8 people, with yard and balcony, kid friendly
Free cancellation
from $441 per night
Find Vacation Rentals in Long Island
Popular Destinations in Long Island
Best Vacation Rentals in Long Island
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Napeague, North Fork
Vacation Rental • 14 Guests • 7 Bedrooms
Napeague, North Fork
Please note this is a partner managed property verified to meet Rove's brand standard by the Rove team. Rove guarantees lowest available rates on properties listed at Rove Travel.Introducing Dunes Lane, a breathtaking 8,000 square foot custom oceanfront mansion, nestled along a secluded private cul-de-sac lane in Amagansett. Designed by award-winning architect Bill Hayes, this architectural masterpiece showcases three extraordinary stories, featuring 7 massive bedrooms, 9 new marble bathrooms, and multiple living areas adorned with 11-foot ceilings and floor-to-ceiling windows, framing stun...
from $9,945 / night
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Shelter Island Heights, North Fork
Vacation Rental • 10 Guests • 5 Bedrooms
Shelter Island Heights, North Fork
Welcome to Sandpoint by Rove Travel, an exclusive Shelter Island retreat recently built on 1.4 acres, just a stone's throw from a sandy beach and across from a 12-acre preserve. This stunning home features five bedrooms, including two master suites and one room with twin beds. Sunlit and spacious, the heart of the home is a well-equipped kitchen with an oversized island overlooking a large pool and landscaped grounds. Sandpoint offers a serene 20x40 gunite pool, making it an unparalleled tranquil retreat on Shelter Island.The heated pool will be guest ready starting May 19, 2025.---Room Con...
from $657 / night
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Noyack, North Fork
Vacation Rental • 12 Guests • 6 Bedrooms
Noyack, North Fork
Experience the best of the Hamptons in style at Meadowood Manor, a luxurious home located in the heart of Sag Harbor. Offering a selection of amenities including a salt water pool, hot tub, outdoor shower, and a full basketball court, guests can relax, unwind, and enjoy the great outdoors. Inside, the open floor concept with an expansive living space and fully-stocked kitchen is perfect for lounging, and 6 luxurious bedrooms provide an idyllic retreat for any group. Conveniently located near Sag Harbor Village and Bridgehampton, as well as a selection of fantastic beaches and restaurants, e...
from $557 / night
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Other holiday ideas and property types in Long Island that might be interesting
Prices and availability
FAQs: Vacation Rentals in Long Island
How much does it cost to book a vacation rental in Long Island?
Long Island is one of the most expensive destinations in the USA. The costs for a vacation rental here amount to around $593 per night.
What time of year offers, on average, the best vacation rental prices in Long Island?
Those who want to be budget-friendly should visit Long Island in February, January, or May, which are the months that offer the most discount, with average prices of $479, $536, and $545 per night, respectively, based on the previous year.
During which months are vacation rentals more expensive in Long Island?
Analyzing the data from last year, we found that costs per night for accommodation here are usually higher, on average, during the months of July ($683), August ($659), and September ($643).
Do I need to plan a trip to Long Island well in advance?
In order to not have problems finding accommodation in Long Island, it is necessary to be proactive as 77% of rentals are usually booked, according to last year's data.
What time of the year can I find more available vacation rentals?
The months when it's easiest to find available accommodation in Long Island are May (the average amount of properties that are available reached 37% of the total last year), February (36%), and June (28%).
When are there fewer vacation rental options available in Long Island?
According to data from last year, the months with the fewest housing options available in Long Island are, in order, August (with 2% of available rentals), July (7%), and September (18%). During this period, the availability is only 9%. It is therefore recommended to reserve far in advance.
Are there many vacation rentals in Long Island?
Holidu collaborates with 5 different partners to give you a choice between 3,200 properties we have in Long Island.