Vacation Rentals in Long Island
Start comparing over 3,613 rentals in Long Island and book at the best price!
- Vacation Rentals ·
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- Long Island
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Child-friendly vacation rentals
East Hampton, North Fork
9.4
Vacation rental for 7 people, with balcony and yard, kid friendly
Free cancellation
from $204 per night
Noyack, North Fork
Vacation rental for 12 people, with terrace and yard, with pets
Free cancellation
from $330 per night
Northwest Harbor, North Fork
Vacation rental for 14 people, with yard and terrace, with pets
Free cancellation
from $768 per night
Southampton (NY), North Fork
Vacation rental for 10 people, with terrace and yard, with pets
Free cancellation
from $782 per night
Vacation rentals with pets allowed
Springs, North Fork
Vacation rental for 13 people, with yard and pool, kid friendly
Free cancellation
from $1,791 per night
Northwest Harbor, North Fork
Vacation rental for 6 people, with yard and balcony, kid friendly
Free cancellation
from $148 per night
Tuckahoe, North Fork
10.0
Vacation rental for 6 people, with yard and terrace, with pets
from $333 per night
Hampton Bays, North Fork
9.6
Vacation rental for 25 people, with yard, with pets
Free cancellation
from $3,644 per night
Vacation rentals in Long Island
Sag Harbor, North Fork
Vacation rental for 6 people, with balcony and yard, kid friendly
Free cancellation
from $3,092 per night
Shelter Island Heights, North Fork
Vacation rental for 12 people, with yard
Free cancellation
from $520 per night
North Sea (NY), North Fork
Vacation rental for 12 people, with yard and balcony, kid friendly
Free cancellation
from $818 per night
Ocean Beach (NY), Suffolk County
10.0
Vacation rental for 12 people, with terrace
from $2,043 per night
Vacation rentals with free cancellation
Nassau County
9.4
Vacation rental for 2 people, with balcony and yard as well as pool
Free cancellation
from $177 per night
Montauk, North Fork
10.0
Vacation rental for 10 people, with hot tub and yard
Free cancellation
from $15,270 per night
Elmont, Nassau County
9.9
Vacation rental for 4 people
Free cancellation
from $351 per night
Centereach, Suffolk County
9.4
Vacation rental for 2 people, with terrace
Free cancellation
from $107 per night
Vacation rentals with hot tub
Fire Island, Suffolk County
8.7
Vacation rental for 10 people, with hot tub and terrace as well as yard
Free cancellation
from $1,378 per night
West Hampton Dunes, North Fork
9.9
Vacation rental for 16 people, with hot tub and balcony, with pets
from $2,358 per night
Fire Island, Suffolk County
10.0
Vacation rental for 6 people, with balcony and hot tub, with pets
from $732 per night
East Hampton North, North Fork
9.4
Vacation rental for 14 people, with hot tub and yard
Free cancellation
from $1,178 per night
Current vacation rental deals in Long Island
East Quogue, North Fork
9.3
Vacation rental for 8 people, with terrace and yard
Fri, 06/12 - Fri, 06/26
$7,095 $6,535 ·
Special Offer
Special offer! The property is offering a 8% discount. Book today to secure this price!
Springs, North Fork
9.9
Vacation rental for 8 people, with yard
Free cancellation
Fri, 06/12 - Fri, 06/26
$21,351 $19,674 ·
Long stay deal
This accommodation offers a 8% discount on long-term stays.
Flanders, North Fork
9.6
Vacation rental for 12 people, with yard and hot tub
Free cancellation
Sat, 06/13 - Tue, 06/23
$25,365 $23,366 ·
Long stay deal
This accommodation offers a 8% discount on long-term stays.
Northwest Harbor, North Fork
9.3
Vacation rental for 8 people, with hot tub and yard
Free cancellation
Sat, 06/13 - Tue, 06/23
$35,677 $32,782 ·
Long stay deal
This accommodation offers a 8% discount on long-term stays.
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Best Vacation Rentals in Long Island
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Sag Harbor, North Fork
Vacation Rental • 6 Guests • 3 Bedrooms
Sag Harbor, North Fork
Welcome to Breakwater, an exquisite private home situated in the heart of Sag Harbor. The first floor features an open concept kitchen, living room, and dining room filled with natural light, while the entire home is equipped with built-in Sonos speakers—perfect for entertaining or relaxing. Amenities include a heated pool, outdoor shower, soaking tub, outdoor grill, and a separate pool house. Plus, Breakwater is conveniently located near Haven’s beach, Foster Memorial town beach, and circle beach, making it the ideal home for any real estate professional looking to enjoy all that the Hampt...
from $3,092 / night
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Northwest Harbor, North Fork
Vacation Rental • 6 Guests • 3 Bedrooms
Northwest Harbor, North Fork
This stunning 3 bedroom, 2.5 bathroom home with a private pool, and a Tesla/EV charger is perfectly located 7 minutes away from Sag Harbor Village and East Hampton Village. Enjoy the perfect indoor/outdoor living experience with over 1700 square feet of outdoor space and 800 square foot pool, with a wrap around deck on the upper floor. There is a spacious living room with treehouse views that leads to an eat-in and dining area with the deck overlooking the pool area. Enjoy the day by the pool, or have a late-night BBQ. This home features a primary bedroom with a king bed and an en-suite bat...
from $148 / night
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Shelter Island Heights, North Fork
Vacation Rental • 12 Guests • 6 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 pool will close for the season on September 29, 2025, and w...
from $520 / 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.