Long Island Holiday Rentals

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Holiday Rentals in Long Island

Cottage in Long Island

10.0 out of 10, Exceptional, (7)
"Great island house! Loved how stocked the kitchen was, we had comfortable beds and even beach chairs and cooler. We would definitely stay here again. "
United States
Serra C.
Updated Long Island Maine Cottage

Aparthotel in Downtown Portland

4.5 star property
9.8 out of 10, Exceptional, (88)
"Loved this place and would definitely stay here next time we go back."
United States
Eleni
The price is NZ$478
includes taxes & fees
5 Jan - 6 Jan 2026
The Weldon Hotel

Holiday Home in Old Orchard Beach

9.8 out of 10, Exceptional, (45)
"Excellent family stay. Backyard is nice and shaded, you can see the ocean from the house and amenities are great. "
United States
Danielle N.
Private, 2nd Floor Cottage with Wonderful Ocean Views- Perfect for Families!

Holiday Home in Bailey Island

10.0 out of 10, Exceptional, (234)
"Tremendous stay, great property and host."
United States
Curtis G.
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

Holiday Home in Old Orchard Beach

9.6 out of 10, Exceptional, (67)
"In one word AMAZING! We rented this property to gather our immediate family, adult children and grandchildren. We had a tragedy in our family as my oldest son was killed, this made our once close family, split apart. This property was so beautiful and such a happy place to be that my prayers were answered my family began the healing process. The location and the views one could not be unhappy. Thank you Jason for helping to make the stay amazing!"
United States
Helen F.
The price is NZ$2,721
includes taxes & fees
4 Jan - 5 Jan 2026
Sensational Beachfront Property Old Orchard Beach, with indoor elevator

Holiday Home in Old Orchard Beach

9.8 out of 10, Exceptional, (97)
"The location was perfect and the house was exceptional. The host and property manager were very responsive and helpful. Would definitely recommend a stay!"
United States
Kathleen C.
The price is NZ$2,377
includes taxes & fees
4 Jan - 5 Jan 2026
Perfect for Families & friends re-unions! Outdoor Hot Tub, 50 yards to the beach!

Holiday Home in Saco

10.0 out of 10, Exceptional, (104)
"Would love to stay here again!! "
United States
Michelle E.
Gorgeous and Unique New England Beach House: Panoramic Views of Saco Bay!

Apartment in West Bayside

5.8 out of 10, (7)
"We didn't stay there at all. Canceled reservation "
United States
Dianne
The price is NZ$243
includes taxes & fees
7 Dec - 8 Dec
Studio Unit Walkable Everywhere

Holiday Home in Grand Beach

2.0 star property
9.0 out of 10, Wonderful, (17)
"Incredibly wonderful beach house. Plenty of room for 8 adults, 6 children. Would recommend for any group with lots of ages and preferences. Helped to create wonderful family reunion."
United States
Ina-Lee B.
Spacious 7-bedroom house with WiFi and AC in fabulous Pine Point Scarborough

Cabin in Old Orchard Beach

9.8 out of 10, Exceptional, (12)
"Walking distance to the board walk. Clean and just enough space for 4 of us. Had everything we needed plus plenty of towels! "
United States
Natalia R.
Charming 2-Bedroom Cottage in Peaceful Old Orchard Beach with WiFi, AC

Apartment in Deering Center

9.2 out of 10, Wonderful, (5)
"Great location for seeing the Portland Head Lighthouse. Comfortable bed."
United States
Michelle S.
Private Entrance Residential Portland

Cottage in Old Orchard Beach

9.8 out of 10, Exceptional, (65)
"Place was great and fenced in backyard for our dog. "
United States
Billy N.
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach

Holiday Home in East Deering

10.0 out of 10, Exceptional, (66)
"Nice stay. Good amenities. "
United States
Laura H.
The price is NZ$1,861
includes taxes & fees
7 Dec - 8 Dec
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

Condo in Old Orchard Beach

9.8 out of 10, Exceptional, (227)
"The view off the deck was breathtaking "
United States
Raymond
The price is NZ$587
includes taxes & fees
6 Dec - 7 Dec
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator

Apartment in Harpswell

9.6 out of 10, Exceptional, (170)
"Very clean beautiful view we definitely enjoyed ourselves "
United States
Ilona F.
1 room luxury ocean front studio cottage

Condo in Old Orchard Beach

9.8 out of 10, Exceptional, (36)
"Great spot...everything was great "
United States
Frank R.
Spectacular Beachfront Condo-Watch sunrise from deck overlooking beach.

Holiday Home in Falmouth

8.8 out of 10, Excellent, (6)
"We had a wonderful stay. Nice comfortable camp. We enjoyed swimming in the lake. "
United States
Darcie B.
Charming 2-bedroom house with AC, WiFi in lovely Falmouth

Apartment in West Bayside

8.6 out of 10, Excellent, (16)
"Host was very accommodating. Apartment worked well for. Description accurate. Would stay again."
United Kingdom
Martha F.
The price is NZ$270
includes taxes & fees
23 Dec - 24 Dec
In-town no frills 2 bedroom apt

Holiday Home in Harpswell

9.4 out of 10, Exceptional, (23)
"We loved our stay! Gorgeous view, lots of thoughtful little amenities. The home was extremely clean and the host was just lovely. "
United States
Catherine O.
Beautiful Oceanfront House- Stunning Water Views

Cottage in Surfside

2.5 star property
8.4 out of 10, Very good, (88)
"Cute and tidy cottage, easy walk to beautiful beach."
United States
Charlotte
Little Miss Cottages
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.
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Top Long Island Hotel Reviews

Find out more about Long Island

Everything you need to know about Long Island holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Long Island holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Long Island holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Long Island holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Long Island. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Long Island holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Long Island holiday rentals we have selected for you start as low as NZ$243 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Long Island rentals

At Expedia, we put the best Long Island holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Long Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Long Island holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Long Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Perfect for Families & friends re-unions! Outdoor Hot Tub, 50 yards to the beach!: This holiday home rental outside of Long Island is located near the beach, and has a fireplace, a balcony and a BBQ 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. It offers a garden, an arcade/games room and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Long Island?

With 7 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 Maine Narrow Gauge Railroad Company and Museum, or get outside and enjoy nature at Sand Beach. In the wider area, you’ll find Fifth Maine Museum and Spring Point Ledge Lighthouse.

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.