We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Holiday Rentals and apartments in Long Island, NY

Professionally managed typically means…
  • Dedicated on-site help
  • Experienced local staff
  • Professional hospitality services
  • Secure credit card payment
Verified property owner typically means…
  • Enhanced property ownership verification in addition to verification of owner name and address via valid credit card
  • Established history of renting online
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
Property owner typically means…
  • Verification of owner name and address via valid credit card
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
Use a credit card to book with our Peace of Mind Protection.
Learn more
Find a rental
Price per night
Min
to
Max
Bedrooms
Any
Amenities
Select
More filters
Find more rentals you can book on TripAdvisor!   We're showing you properties you can book on TripAdvisor first.
All 262 Rentals in Long Island
loading...
Sort by
From
€179
Per Night
Bridgehampton
1 Bedroom, 1 Bathroom, Sleeps 2
16 photos Details
Reviews (2) Make Enquiry
From
€130
Per Night
Southold
2 Bedrooms, 1 Bathroom, Sleeps 4
13 photos Details
Reviews (1) Make Enquiry
Make Enquiry
5 of 5 stars Reviewed 3 June 2014
I rented both units in this cottage a few years back and was pleased to see that the property was lovely as ever. I rented both cottages again this time for a girl’s getaway...
See all reviews
From
€521
Per Night
Quogue
4 Bedrooms, 3 Bathrooms, Sleeps 6
15 photos Details
Reviews (1) Make Enquiry
5 of 5 stars Reviewed 2 June 2014
Our stay at Vince's place was wonderful! Vince was responsive via email and phone and very accommodating regarding our arrival and departure times. The place is located a short...
See all reviews
Also consider
Charming Home 100 paces to Sag Harbor Bay Beach
3 Bedrooms, sleeps 8
€261 - €372 / night
Private Amagansett Estate
5 Bedrooms, sleeps 12
€2,234 / night
Soundfront 1910 Rustic Secluded Cottage
2 Bedrooms, sleeps 7
€266 / night
Sag Harbor Bridgehampton 5min Guest Suite
1 Bedroom, sleeps 3
€112 - €279 / night
From
€506
Per Night
Water Mill
3 Bedrooms, 3 Bathrooms, Sleeps 6
10 photos Details
Reviews (1) Make Enquiry
From
€1,787
Per Week
Southold
2 Bedrooms, 1 Bathroom, Sleeps 6
12 photos Details
Reviews (2) Make Enquiry
From
€302
Per Night
East Hampton
3 Bedrooms, 2 Bathrooms, Sleeps 6
10 photos Details
Reviews (2) Make Enquiry
From
€559
Per Night
Fair Harbor
4 Bedrooms, 1 Bathroom, Sleeps 7
16 photos Details
Reviews (1) Make Enquiry
Make Enquiry
4 of 5 stars Reviewed 4 July 2012
I've been renting in Fair Harbor for over 20 years. What you need in a Fire Island rental is to be near the ferry, the store but still have and quiet and privacy. You need beach...
See all reviews
From
€261
Per Night
Southampton
3 Bedrooms, 2 Bathrooms, Sleeps 7
16 photos Details
Reviews (1) Make Enquiry
Make Enquiry
5 of 5 stars Reviewed 29 June 2014
The house is in a beautiful area that is convenient to everything. I felt safe and comfortable, had a very relaxing experience staying there- and the home owner couldn't be...
See all reviews
Get the List
From
€220
Per Night
Southold
3 Bedrooms, 1 Bathroom, Sleeps 6
17 photos Details
Reviews (10) Make Enquiry
Make Enquiry
5 of 5 stars Reviewed 14 July 2014
My family was very pleased with these accommodations. We were all very comfortable. The place was very clean and well equipped for our 5 day stay. The location is absolutely...
5 of 5 stars Reviewed 19 April 2014
We had a very relaxing long weekend, giving our daughter and her husband a break from New York and were lucky to get excellent weather. The house is well equipped and the location...
See all reviews
From
€660
Per Night
Fire Island
3 Bedrooms, 2 Bathrooms, Sleeps 6
11 photos Details
Reviews (1) Make Enquiry
From
€119
Per Night
East Hampton
1 Bedroom, 2 Bathrooms, Sleeps 2
8 photos Details
Reviews (1) Make Enquiry
Make Enquiry
4 of 5 stars Reviewed 7 July 2014
If your looking for a CLEAN beautiful place to stay in a peaceful part of the Hampton's (NOT party city) at a great rate. Then look no more. I was so worried booking but was...
See all reviews
From
€369
Per Night
Sag Harbor
2 Bedrooms, 1 Bathroom, Sleeps 6
21 photos Details
Reviews (3) Make Enquiry
From
€894
Per Night
Fire Island
4 Bedrooms, 3 Bathrooms, Sleeps 8
6 photos Details
Reviews (1) Make Enquiry
From
€298
Per Night
Cutchogue
2 Bedrooms, 1 Bathroom, Sleeps 6
26 photos Details
Reviews (1) Make Enquiry
5 of 5 stars Reviewed 23 September 2013
I recently made a trip to Long Island to just get away for a couple days and to catch up with an old friend who lives on the North Fork. Lucky for me this lovely cottage was...
See all reviews
From
€1,452
Per Night
Sag Harbor
7 Bedrooms, 8 Bathrooms, Sleeps 14
25 photos Details
Reviews (4) Make Enquiry
From
€248
Per Night
East Hampton
5 Bedrooms, 3 Bathrooms, Sleeps 10
24 photos Details
Reviews (1) Make Enquiry
From
€298
Per Night
East Hampton
3 Bedrooms, 2 Bathrooms, Sleeps 6
24 photos Details
Reviews (6) Make Enquiry
From
€261
Per Night
Cutchogue
3 Bedrooms, 4 Bathrooms, Sleeps 6
9 photos Details
Reviews (1) Make Enquiry
5 of 5 stars Reviewed 28 May 2014
This was our first trip to the North Fork and it was outstanding. We loved the location...lots to see and do in the immediate area and easy access via ferries to Shelter Island...
See all reviews
From
€372
Per Night
Water Mill
3 Bedrooms, 2 Bathrooms, Sleeps 8
12 photos Details
Reviews (1) Make Enquiry
Make Enquiry
5 of 5 stars Reviewed 24 June 2014
This was our first experience renting a house and I was a bit anxious. However the whole procedure through Trip Advisor was painless and the owner and house both turned out to be...
See all reviews
From
€74
Per Night
Huntington
1 Bedroom, 1 Bathroom, Sleeps 4
15 photos Details
Reviews (15) Make Enquiry
5 of 5 stars Reviewed 13 November 2013
We really felt at home in this cozy apartment. It has a full kitchen, nice full bath w/tub, and full living area all on the first floor. The queen bedroom is upatairs in the loft...
See all reviews
From
€186
Per Night
East Hampton
4 Bedrooms, 4 Bathrooms, Sleeps 8
16 photos Details
Reviews (5) Make Enquiry
Make Enquiry
5 of 5 stars Reviewed 6 October 2013
We first stayed here in 2012 for 6 nights and because we enjoyed it so much, this year we stayed for 13 nights and it was how we remembered it. Heloisa is a charming, friendly...
2 of 5 stars Reviewed 15 July 2013
Located in an residential street some distance from the center of East Hampton this B&B was neither cozy nor charming. There was nothing awful but the rooms are small, breakfast...
See all reviews
From
€372
Per Night
Sag Harbor
3 Bedrooms, 2 Bathrooms, Sleeps 10
22 photos Details
Reviews (1) Make Enquiry
From
€428
Per Night
Montauk
6 Bedrooms, 4 Bathrooms, Sleeps 14
21 photos Details
Reviews (4) Make Enquiry
From
€261
Per Night
East Hampton
4 Bedrooms, 3 Bathrooms, Sleeps 6
36 photos Details
Reviews (1) Make Enquiry
From
€298
Per Night
Orient
3 Bedrooms, 2 Bathrooms, Sleeps 5
11 photos Details
Reviews (1) Make Enquiry
Make Enquiry
3 of 5 stars Reviewed 29 May 2014
Great area but home is in poor condition. Decorated very cute and clean but all uneven floors, very cold inside house, no tv (although it was promised), not worth the price...
See all reviews
From
€108
Per Night
Montauk
Studio, 1 Bathroom, Sleeps 4
18 photos Details
Reviews (1) Make Enquiry
Make Enquiry
3 of 5 stars Reviewed 21 May 2014
each unit is individually owned. that means that every room is different. I booked with the owner of room 108 (apparently a nice room, as per other reviews). he never answered any...
See all reviews
From
€451
Per Night
3 Bedrooms, 4 Bathrooms, Sleeps 6
14 photos Details
Make Enquiry
From
€7,104
Per Week
5 Bedrooms, 5 Bathrooms, Sleeps 10
14 photos Details
Make Enquiry
From
€223
Per Night
Southold
2 Bedrooms, 1 Bathroom, Sleeps 4
40 photos Details
Make Enquiry
From
€298
Per Night
Peconic
3 Bedrooms, 1 Bathroom, Sleeps 6
11 photos Details
Make Enquiry
From
€205
Per Night
Mattituck
4 Bedrooms, 1 Bathroom, Sleeps 6
25 photos Details
Make Enquiry
From
€249
Per Night
Hampton Bays
4 Bedrooms, 2 Bathrooms, Sleeps 8
14 photos Details
Make Enquiry
From
€559
Per Night
Quogue
4 Bedrooms, 3 Bathrooms, Sleeps 8
36 photos Details
Make Enquiry
From
€223
Per Night
Cutchogue
2 Bedrooms, 2 Bathrooms, Sleeps 4
6 photos Details
Make Enquiry
From
€149
Per Night
East Marion
4 Bedrooms, 3 Bathrooms, Sleeps 9
7 photos Details
Make Enquiry
From
€298
Per Night
Sag Harbor
4 Bedrooms, 2 Bathrooms, Sleeps 10
27 photos Details
Make Enquiry
From
€186
Per Night
Rocky Point
3 Bedrooms, 1 Bathroom, Sleeps 5
23 photos Details
Make Enquiry
Make Enquiry
5 of 5 stars Reviewed 15 July 2014
Our first time on eastern Long Island - the trip out from the hectic pace of NYC slowly turns from urban to beautiful parkland, finally ending at quaint Rocky Point LI. The home...
See all reviews
From
€447
Per Night
Quogue
5 Bedrooms, 6 Bathrooms, Sleeps 12
14 photos Details
Make Enquiry
From
€596
Per Night
Bridgehampton
4 Bedrooms, 2 Bathrooms, Sleeps 8
8 photos Details
Make Enquiry
From
€298
Per Night
Montauk
1 Bedroom, 1 Bathroom, Sleeps 6
11 photos Details
Make Enquiry
Go to map view
Book Online(200)
Use filters to find the best results!

Suitability

  • Wheelchair access (30)
  • Elder access (126)
  • Suitable for children (165)
  • Pet friendly (76)
  • Smoking allowed (8)

Amenities

  • Other outdoor space (208)
  • Internet (195)
  • Air Conditioning (190)
  • Grill (185)
  • Parking (139)
  • View all amenities
List your property for free!
List your accommodation
for free on our website.
Reach millions worldwide.
Add a Listing


In partnership with
Get the List
Rentals in Long Island
Apartment holiday in Long Island

New York welcomes huge numbers of visitors every year who are attracted to this iconic American city for its shopping, Broadway musicals, cuisine and breadth of visitor attractions. Long Island is situated to the south east of the city and includes the well known metropolitan boroughs of Queens and Brookyln. However, it also contains the more rural counties of Suffolk and Nassau which offer stunning beaches and an insight into the lives of the super rich. You can experience a Long Island holiday without paying through the teeth by hiring an apartment.

Greenport – wine, boats and carousel rides

Greenport is a little harbour village in Suffolk County and exudes charm with its bustling marina, tall ships, and 1920s carousel. Kids will love checking out all the boats at Mitchell Park, as well as taking a spin on the historic carousel, and you can also hop onto a ferry for a quick trip across to Shelter Island, which is a safe haven for wildlife due to its large wetlands.

Back in Greenport, make sure you check out the Railroad and Maritime museums which give an insight into the region’s historic past as a centre of whaling and ship building. Suffolk County is also famed for its wineries and there are several within close proximity to Greenport that offer wine tasting and tours. You can also sample the county’s fine wines in one of the local eateries which will be a perfect way to end the day as the sun sets over the harbour.

Beaches along the Hamptons

The area known as The Hamptons is one of the most wealthy in the United States and is comprised of a series of picturesque seaside villages. It’s renowned for its popularity with A-list celebrities and the attraction of the area will become apparent when you see those blue skies and golden beaches and consider its convenient proximity to the Big Apple. If sunbathing and other beach-related activities are your thing, then you’ll be in paradise and, as you’d expect, there’s plenty of great restaurants and drinking establishments to choose from.

Historic parks and stately homes

Across in Nassau County you’ll find the spacious and hugely impressive Planting Fields Arboretum State Historic Park, which covers over 400 acres and features a stunning collection of greenhouses, gardens, and offers guaranteed colour and pleasant walks.

Also within the boundaries of Nassau you’ll also find Sagamore Hill, which was the home of Theodore Roosevelt the 26th President of the United States. Built in 1884, it’s now listed on the National Register of Historic Places and tours are open to the public. Included within the premises is the Theodore Roosevelt Museum.