Long Island Holiday Rentals

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Holiday Rentals in Long Island

The Weldon Hotel

4.5 star property
9.8 out of 10, Exceptional, (66)
"Absolutely beautiful place to stay. "
The price is NZ$842
includes taxes & fees
23 July - 24 July
The Weldon Hotel

68 East Grand Ave

3.0 star property
8.0 out of 10, Very good, (4)
"nice place close to all"
68 East Grand Ave

Cozy and Quiet Beautiful Home One Bedroom Private Bathroom in Portland Maine.

2.0 star property
10.0 out of 10, Exceptional, (1)
"The property was as described, clean, and in a quiet neighborhood. Conveniently located to many local attractions. Check in and check out process was smooth. Overall enjoyed my stay very much. "
Cozy and Quiet Beautiful Home One Bedroom Private Bathroom in Portland Maine.

Studio Unit Walkable Everywhere

The price is NZ$344
includes taxes & fees
22 July - 23 July
Studio Unit Walkable Everywhere

Sensational Beachfront Property Old Orchard Beach, with indoor elevator

9.6 out of 10, Exceptional, (61)
"Beautiful location even in the offseason, gorgeous house with plenty of room for guests. Very close to Portland for a nice dinner and some drinks. We also went and played some golf at summit in OOB and had a blast. Outdoor grill was perfect and overall we had a great time! Excellent host excellent location and perfect for what we needed. Would recommend highly."
Sensational Beachfront Property Old Orchard Beach, with indoor elevator

New Listing! AmongstTheAspens - Off Grid Tiny House in a Serene Location

10.0 out of 10, Exceptional, (2)
"It was a privilege to have the opportunity to experience this truly amazing property. First of all, the tiny house was immaculate, and every available space was utilized perfectly. The outdoor space was so comfortable, I spent every morning on the deck reading, and we spent every evening around the fire pit. The boys explored the woods around the creek and I cooked three meals a day in that tiny kitchen! It’s hard to believe that four of us were so comfortable, but it is a testament to the hosts...
The price is NZ$518
includes taxes & fees
30 July - 31 July
New Listing! AmongstTheAspens - Off Grid Tiny House in a Serene Location

Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach

9.8 out of 10, Exceptional, (48)
"Very nice property to stay at in Old Orchard Beach! It’s a very quiet neighborhood with a fully enclosed backyard, which was nice for my dog. It’s only a 15 minute walk to the beach, which is very convenient as well. Only thing that I would have liked was to have access to regular cable on the tv, since I couldn’t watch NESN with Roku. But still would give this place 5 stars! We had a lovely time. 😊"
The price is NZ$654
includes taxes & fees
2 Aug - 3 Aug
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach

Gorgeous ocean-front home with stunning beach views

9.6 out of 10, Exceptional, (114)
"This property worked well for us. Ocean view was fantastic, beds were comfy, garage was handy for our car. Good in shoulder season, would like to come back and try it in the summer."
Gorgeous ocean-front home with stunning beach views

Little Miss Cottages

2.5 star property
8.4 out of 10, Very good, (83)
"Place was great "
Little Miss Cottages

Come enjoy 7 miles of beaches in sunny OOB in this 2 bedroom condo.

7.4 out of 10, Good, (26)
"The cute apartment was clean with super comfy beds and very convenient to everything in OOB."
The price is NZ$1,035
includes taxes & fees
29 July - 30 July
Come enjoy 7 miles of beaches in sunny OOB in this 2 bedroom condo.

100 feet from the ocean 3 bedroom cottage 420 friendly

8.6 out of 10, Excellent, (17)
"Our family of 5 stayed here with our dog. This place has it all and we wanted for nothing. Stocked with towels, everything you would need in the kitchen. There’s even a washer and dryer on site. Right next the beach and a short walk to the pier. It was very clean and well taken care of. We will definitely be back!"
100 feet from the ocean 3 bedroom cottage 420 friendly

Bright and airy condo with beachfront access and walkable entertainment nearby

8.0 out of 10, Very good, (1)
"Not a bad spot. Just don't expect too much in the way of frills and be prepared to be flexible with sleeping/parking arrangements."
Bright and airy condo with beachfront access and walkable entertainment nearby

2 bedroom cottage

9.6 out of 10, Exceptional, (4)
"quiet, clean, short walk to beach"
2 bedroom cottage

Ocean Front Penthouse suite, Luxurious 2-bedroom,1350 sqft,2 decks, A++ location

10.0 out of 10, Exceptional, (12)
"Stunning property and great location! "
The price is NZ$1,449
includes taxes & fees
20 July - 21 July
Ocean Front Penthouse suite, Luxurious 2-bedroom,1350 sqft,2 decks, A++ location

Idyllic 3 Bed/2Bath condo in Old Orchard Beach, steps to the beach

8.0 out of 10, Very good, (3)
"Loved how close it was to everything,could be a little more updated on a couple of things"
Idyllic 3 Bed/2Bath condo in Old Orchard Beach, steps to the beach

Beach across the Street. Pets OK

8.8 out of 10, Excellent, (27)
"Perfect spot! Right near the beach and walking distance to all the best places. Very clean and chill little place perfect for what I was going for."
The price is NZ$565
includes taxes & fees
20 July - 21 July
Beach across the Street. Pets OK

Come enjoy 7 miles of beaches in sunny OOB in this 3 bedroom condo!

8.2 out of 10, Very good, (29)
"Good location and clean"
The price is NZ$1,565
includes taxes & fees
20 July - 21 July
Come enjoy 7 miles of beaches in sunny OOB in this 3 bedroom condo!

Beachfront Unit 17 | Right on Old Orchard Beach!

10.0 out of 10, Exceptional, (1)
"It was Amazing right next to the beach , def will be coming back !!"
Beachfront Unit 17 | Right on Old Orchard Beach!

Come enjoy 7 miles of beaches in Sunny OOB in this 2 bedroom condo.

8.6 out of 10, Excellent, (55)
"Easy access and check in. The location was just what we wanted with it close to the beach."
The price is NZ$1,139
includes taxes & fees
3 Aug - 4 Aug
Come enjoy 7 miles of beaches in Sunny OOB in this 2 bedroom condo.

Charming 2-Bedroom Cottage in Peaceful Old Orchard Beach with WiFi, AC

10.0 out of 10, Exceptional, (1)
"We enjoyed our stay there .the cottage was clean loved the charm of the place. Host was very helpful. Will return again. "
Charming 2-Bedroom Cottage in Peaceful Old Orchard Beach with WiFi, AC
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

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?

Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach: This holiday home rental outside of Long Island offers a garden, a selection of games and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

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 Portland Observatory, or get outside and enjoy nature at Sand Beach. In the wider area, you’ll find East End Beach and Southern Maine Community College.

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.