Long Island Holiday Rentals

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Check prices for these dates

In two weeks
2 Jan - 4 Jan
In two months
13 Feb - 15 Feb
In three months
13 Mar - 15 Mar
In four months
10 Apr - 12 Apr

Our top choices for Long Island holiday rentals

Fridge, oven, stovetop, coffee/tea maker
Updated Long Island Maine Cottage

Cottage in Long Island

Updated Long Island Maine Cottage
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
Private kitchen
The Weldon Hotel

Aparthotel in Downtown Portland

The Weldon Hotel
4.5 star property
9.8 out of 10, Exceptional, (90)
"Loved this place and would definitely stay here next time we go back."
United States
Eleni
The price is HK$1,600
HK$2,328 total
includes taxes & fees
25 Dec - 26 Dec
The Weldon Hotel
Beach
Private, 2nd Floor Cottage with Wonderful Ocean Views- Perfect for Families!

Holiday Home in Old Orchard Beach

Private, 2nd Floor Cottage with Wonderful Ocean Views- Perfect for Families!
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!
On the beach
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

Holiday Home in Bailey Island

New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach
10.0 out of 10, Exceptional, (234)
"Great property with amazing views."
United States
katie b.
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach
Interior
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator

Condo in Old Orchard Beach

Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator
9.8 out of 10, Exceptional, (227)
"The view off the deck was breathtaking "
United States
Raymond
The price is HK$1,362
HK$2,655 total
includes taxes & fees
14 Jan - 15 Jan 2026
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator
On the beach
Sensational Beachfront Property Old Orchard Beach, with indoor elevator

Holiday Home in Old Orchard Beach

Sensational Beachfront Property Old Orchard Beach, with indoor elevator
9.6 out of 10, Exceptional, (67)
"Great location, clean and the perfect beach front property!! "
United States
Alanna M.
The price is HK$5,441
HK$10,640 total
includes taxes & fees
12 Jan - 13 Jan 2026
Sensational Beachfront Property Old Orchard Beach, with indoor elevator
Interior
Charming Studio apartment with WiFi, AC in welcoming Portland

Apartment in Munjoy Hill

Charming Studio apartment with WiFi, AC in welcoming Portland
9.6 out of 10, Exceptional, (11)
"A great location and a comfortable place to stay!"
United States
Andrew K.
The price is HK$875
HK$1,650 total
includes taxes & fees
17 Dec - 18 Dec
Charming Studio apartment with WiFi, AC in welcoming Portland
1 bedroom, bed sheets
Studio Unit Walkable Everywhere

Apartment in West Bayside

Studio Unit Walkable Everywhere
5.8 out of 10, (7)
"We didn't stay there at all. Canceled reservation "
United States
Dianne
The price is HK$531
HK$1,090 total
includes taxes & fees
17 Dec - 18 Dec
Studio Unit Walkable Everywhere
Beach nearby
Perfect for Families & friends re-unions! Outdoor Hot Tub, 50 yards to the beach!

Holiday Home in Old Orchard Beach

Perfect for Families & friends re-unions! Outdoor Hot Tub, 50 yards to the 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 HK$4,663
HK$9,682 total
includes taxes & fees
11 Jan - 12 Jan 2026
Perfect for Families & friends re-unions! Outdoor Hot Tub, 50 yards to the beach!
Smart TV
Charming 2-Bedroom Cottage in Peaceful Old Orchard Beach with WiFi, AC

Cabin in Old Orchard Beach

Charming 2-Bedroom Cottage in Peaceful Old Orchard Beach with WiFi, AC
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
TV
Private Entrance Residential Portland

Apartment in Deering Center

Private Entrance Residential Portland
9.2 out of 10, Wonderful, (5)
"Check in was simple. Quaint place. "
United States
Danielle C.
Private Entrance Residential Portland
Interior
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach

Cottage in Old Orchard Beach

Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach
9.8 out of 10, Exceptional, (65)
"Nice spot to stay with our pup! Chris was available and helpful, and it’s clear he takes care of his property. "
United States
John and Lori W.
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach
Smart TV, fireplace, DVD player, books
New Well Built Elegant Home on the Water 2 miles to Freeport, 9 to Portland!

Holiday Home in South Freeeport

New Well Built Elegant Home on the Water 2 miles to Freeport, 9 to Portland!
9.8 out of 10, Exceptional, (197)
"My family had a wonderful time! The house was perfect for us. It was comfy and so well equipped.The location was absolutely perfect. The neighborhood was quiet and friendly. "
United States
Maryann A.
New Well Built Elegant Home on the Water 2 miles to Freeport, 9 to Portland!
Exterior
Charming 2-bedroom house with AC, WiFi in lovely Falmouth

Holiday Home in Falmouth

Charming 2-bedroom house with AC, WiFi in lovely 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
Property grounds
Spectacular Beachfront Condo-Watch sunrise from deck overlooking beach.

Condo in Old Orchard Beach

Spectacular Beachfront Condo-Watch sunrise from deck overlooking 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.
Interior
Popham Beach Direct Oceanfront Cottage Steps to the sand

Cottage in Phippsburg

Popham Beach Direct Oceanfront Cottage Steps to the sand
9.8 out of 10, Exceptional, (69)
"It was everything we hoped for!"
United States
Kate L.
Popham Beach Direct Oceanfront Cottage Steps to the sand
Terrace/patio
1 room luxury ocean front studio cottage

Apartment in Harpswell

1 room luxury ocean front studio cottage
9.6 out of 10, Exceptional, (171)
"Very clean beautiful view we definitely enjoyed ourselves "
United States
Ilona F.
1 room luxury ocean front studio cottage
Interior
Back yard paradise

Holiday Home in Portland

Back yard paradise
9.8 out of 10, Exceptional, (22)
"Excellent home overall! Great equipment, great kitchen, great pool, nice patio! Easy access to the home and driveway! Probably the best house I’ve stayed in ! "
United States
Justin J.
Back yard paradise
Exterior
Little Miss Cottages

Cottage in Surfside

Little Miss Cottages
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
Exterior
Beautiful Oceanfront House- Stunning Water Views

Holiday Home in Harpswell

Beautiful Oceanfront House- Stunning Water Views
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
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

Holiday Inn Portland-By the Bay by IHG

Holiday Inn Portland-By the Bay by IHG

10/10 Excellent
"We had a great time. Holiday Inn Portland - By the Bay is in a great location and it was economical. The shuttle service was a plus and it saved us some money on Ubers since it was cold. I would definitely come back. "
Allan 4-night trip
Posted 1 day ago
Holiday Inn Portland-By the Bay by IHG

Find out more about Long Island

Search for holiday rentals in Long Island on Expedia! You can easily find your home rentals, villas, holiday apartments in Long Island using one of the methods below:

  • View our selection of featured holiday rentals in Long Island
  • Use the map to find apartments and other holiday homes in the Long Island neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Long Island while they last

Look no further and take a look at our great range of rental properties in Long Island!

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 East End Beach and Willard Beach.

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.