Long Island Holiday Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Long Island

2 duplex
3.0 star property
2 duplex
Full sized home
9.6 out of 10, Exceptional, 4 reviews
"Great place to stay. Host was helpful and responsive."
The price is NZ$560
includes taxes & fees
23 June - 24 June
23 Jun - 24 Jun
Full sized home
NEW TO THE MARKET - 1 block from the beach!
10.0 out of 10, Exceptional, 8 reviews
"This property isn't large, but was absolutely perfect for a quick getaway for my husband and me. The owners were extremely responsive, and provide you with all of the kitchen/bathroom essentials that you need. The condo was very clean, in walking distance to shops/restaurants/the pier, and the beach is just a short walk across the street. We look forward to renting here again in the future!"
The price is NZ$709
includes taxes & fees
10 July - 11 July
10 Jul - 11 Jul
NEW TO THE MARKET - 1 block from the beach!
Gorgeous ocean-front home with stunning beach views
9.6 out of 10, Exceptional, 76 reviews
"Great little condo. Right on the beach! Balcony is wonderful, as is the view from the master. Second bedroom is definitely a “kids” room with the two bunk beds. Garage was great for a car, would not fit the height of a truck"
Gorgeous ocean-front home with stunning beach views
Laurel Shore Cottage with Seasonal Private Tidal Dock, Pet friendly.
9.8 out of 10, Exceptional, 27 reviews
"We spent our 19th wedding anniversary here. It was the perfect romantic getaway. The views are stunning and the location is tranquil. Just a short drive to the general store for necessities, and Uber Eats delivers. We didn’t want to leave. Would 100% stay here again."
Laurel Shore Cottage with Seasonal Private Tidal Dock, Pet friendly.
Third-Floor Coastal Condo W/ Modern Updates, High-Speed WiFi & Perfect Location
7.4 out of 10, Good, 25 reviews
"The unit has a really nice view of downtown and the pier. Cool view of the ferris wheel lit up at night. At first glance, the unit is nicely decorated. However, it needs to be refreshed - there are chunks missing out of the walls, things falling apart, ongoing water damage next to the tub. Maintenance from the building came by on the first morning of the stay to check on the kitchen sink because there was a massive leak happening to the unit below. Overall, it seemed as if no one has been...
Third-Floor Coastal Condo W/ Modern Updates, High-Speed WiFi & Perfect Location
2 min walk to the beach. Pet friendly condo
8.8 out of 10, Excellent, 26 reviews
"Overall a good stay for the price and convenient to everything. Kinda dated and could use some upgrades. "
The price is NZ$514
includes taxes & fees
26 June - 27 June
26 Jun - 27 Jun
2 min walk to the beach. Pet friendly condo
Little Miss Cottages
2.5 star property
8.2 out of 10, Very good, 68 reviews
"Perfect place for a family to stay for a fair price if you want to stay a few nights and tour around the rest of Maine. Beach was wonderful! "
Little Miss Cottages
Charming Cottage Steps to Pine Point Bch - 1 mile OOB outside Scarborough w/ AC
9.8 out of 10, Exceptional, 12 reviews
"This is a great spot to stay no matter what time of the year!! Completely enjoyed my stay!!"
The price is NZ$1,189
includes taxes & fees
19 July - 20 July
19 Jul - 20 Jul
Charming Cottage Steps to Pine Point Bch - 1 mile OOB outside Scarborough w/ AC
Artsy Apt/Private Rooftop Deck!/Old Port Arts Dist
10.0 out of 10, Exceptional, 20 reviews
"This apartment is fantastic! Great location, perfectly appointed, and Dena was awesome with her communications. The roof deck is a great bonus."
Artsy Apt/Private Rooftop Deck!/Old Port Arts Dist
4 min walk to the beach. A large 3DB Apt. Pets OK
8.6 out of 10, Excellent, 7 reviews
"We found this place and booked after seeing it was pet friendly and close to the beach which was a must for our beach loving family and pups. Our stay was lovely- it’s a few blocks to the beach and into the main town area. The place was clean, had a good amount of space, was quiet, and a small deck area to sit outside. Communications with the host were easy and they checked in on us part way through to ensure our stay was going well."
The price is NZ$864
includes taxes & fees
1 July - 2 July
1 Jul - 2 Jul
4 min walk to the beach. A large 3DB Apt. Pets OK
Elegant condo - walk to Portland's best restaurants & Old Port
9.4 out of 10, Exceptional, 47 reviews
"My two sisters and I loved everything about the place especially the kitchen and the temperature control via AC or heat. The only concern about the place is that it took 1-3 tries each time we had to unlock the front door by code. There was supposed to be music to help but couldn't really hear anything. May need some attention but have to admit we never alerted anyone at the time thinking it was related to our ineptitude! I tried to do this review on the Vacasa site but the page never came up...
The price is NZ$834
includes taxes & fees
8 July - 9 July
8 Jul - 9 Jul
Elegant condo - walk to Portland's best restaurants & Old Port
Amazing beachside condo w/private balcony/free WiFi/full kitchen - near Portland
8.2 out of 10, Very good, 33 reviews
"I rated this property a 4 and not lower because of its location. It is front-facing to the ocean, and that is always a gem in my book. Sleeping to the sound of the waves is amazing. The property management (Vacasa) was flawless in their communication and the housekeeping staff did a great job cleaning what they were responsible for cleaning. BUT....... this unit is in dire need of some deep cleaning and at a minimum some TLC in painting and in fixing what doesn't work (i.e., windows, toilet...
Amazing beachside condo w/private balcony/free WiFi/full kitchen - near Portland
Spacious 4BR, Walk to Downtown & Pier, Sleeps 10
The price is NZ$1,483
includes taxes & fees
20 June - 21 June
20 Jun - 21 Jun
Spacious 4BR, Walk to Downtown & Pier, Sleeps 10
Everybody's favorite Maine beach location
9.4 out of 10, Exceptional, 13 reviews
"The property was clean and spacious for four 25 year old men to comfortably stay for the weekend."
Everybody's favorite Maine beach location
Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants
9.8 out of 10, Exceptional, 89 reviews
"Six of us stayed for our daughter's graduation. Nicely appointed property! We were able to walk to dinner, and it was a short drive to our other activities. Highly recommend!"
Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants
350 Yards to the beach. Pet friendly!
8.4 out of 10, Very good, 24 reviews
"Unit was clean but small enough for privacy"
The price is NZ$446
includes taxes & fees
20 June - 21 June
20 Jun - 21 Jun
350 Yards to the beach. Pet friendly!
Oceanfront Condo! Spectacular Views From Private Large Balcony
9.0 out of 10, Wonderful, 114 reviews
"I loved the location!!! Great little place...restaurant downstairs was great."
The price is NZ$1,198
includes taxes & fees
9 July - 10 July
9 Jul - 10 Jul
Oceanfront Condo! Spectacular Views From Private Large Balcony
Large 2BD cottage 10 min to Pier & Beach Pets ok
9.4 out of 10, Exceptional, 17 reviews
"The cottage was clean and accurately described. It was perfect for our needs and we are already looking forward to staying there again in the future."
The price is NZ$597
includes taxes & fees
24 June - 25 June
24 Jun - 25 Jun
Large 2BD cottage 10 min to Pier & Beach Pets ok
East Grand Ave Fabulous Cottage
9.0 out of 10, Wonderful, 112 reviews
"Very good location. Walked everywhere and very close to the beach. The owner was super receptive when there was an understandable appliance problem. I would definitely return."
East Grand Ave Fabulous Cottage
Don't see what you're looking for?
See all available properties in Long Island
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other types of properties in Long Island you may be interested in

Casco Bay Hotel, Ascend Hotel Collection
3.5 star property
8.6 out of 10, Excellent, 1,624 reviews
"Room was comfortable. It had a decent fitness room. Staff was very helpful. Breakfast was very lacking, to say the least. Other than the shopping mall, there's not much by this hotel. You pretty much are taking an Uber downtown for any food or drink options."
The price is NZ$229
includes taxes & fees
23 June - 24 June
23 Jun - 24 Jun
Casco Bay Hotel, Ascend Hotel Collection
The Westin Portland Harborview
4.0 star property
8.6 out of 10, Excellent, 1,043 reviews
"All the staff were so helpful and kind."
The price is NZ$501
includes taxes & fees
24 June - 25 June
24 Jun - 25 Jun
The Westin Portland Harborview
Portland Harbor Hotel
4.0 star property
9.0 out of 10, Wonderful, 1,203 reviews
"Restful night sleep, loved all the amenities."
The price is NZ$586
includes taxes & fees
2 July - 3 July
2 Jul - 3 Jul
Portland Harbor Hotel
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Long Island holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Long Island. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Long Island. Seeing all the best attractions is bound to make you fall in love with Long Island. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Long Island short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there holiday rentals in Long Island?

Yes, there are holiday rentals close to the most popular sights in Long Island, or you can select a more secluded option if you're looking for a relaxing stay. Long Island is known for its restaurants and shopping. Make sure you have time to check out the beaches while you're in the area.

What are some of the best holiday rentals that Long Island has to offer?

Bliss Beach House ♦ Huge Ocean View Rooftop Deck ♦ : This holiday home rental outside of Long Island is located on the beach, and has a balcony, a BBQ and air conditioning to put you at ease in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of books in this rental home to help you unwind.

How many holiday rentals are there in Long Island?

With 8 Expedia holiday rentals, you're guaranteed to find just the right place for your Long Island stay.

What’s there to see and do in Long Island?

While exploring the area, visit family-friendly sights like Aquaboggan Water Park, or get outside and enjoy nature at Sand Beach. In the wider area, you’ll find East End Beach and Eastern Promenade.

What’s a holiday rental in Long Island like?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Long Island. Holiday rentals feature amenities such as patios, hot tubs and fire pits so you'll feel just like you're at home. If you're concerned about cleanliness, holiday rentals can provide a sense of seclusion away from public hotel lifts and lobbies bustling with people while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular choice for small groups.

Recent reviews of Long Island properties
Expedia verified reviews