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Our top choices for Long Island holiday rentals

1. Ocean View East End Studio in a Historic Victorian

Ocean View East End Studio in a Historic Victorian
Portland
9.8 out of 10, Exceptional, (110 reviews)
"Lovely view and accessibility to the Old Port area. Enjoyed our relaxing stay! Thanks Dan! "
United States
David E.
The price is £346
includes taxes & fees
23 Aug - 24 Aug
Ocean View East End Studio in a Historic Victorian

2. Willard Square Family Home

Willard Square Family Home
Willard Beach
9.8 out of 10, Exceptional, (12 reviews)
"Great location, close to Old Port. Great bakery/coffee and ice cream next door. House was clean and comfortable!"
United States
Steve S.
The price is £446
includes taxes & fees
23 Aug - 24 Aug
Willard Square Family Home

3. Charming Studio apartment with WiFi, AC in welcoming Portland

Charming Studio apartment with WiFi, AC in welcoming Portland
Munjoy Hill
9.4 out of 10, Exceptional, (25 reviews)
"Great place! We would definitely return if we were in the area."
United States
Preston
The price is £247
includes taxes & fees
17 Sept - 18 Sept
Charming Studio apartment with WiFi, AC in welcoming Portland

4. Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
East Deering
10.0 out of 10, Exceptional, (79 reviews)
"Everything was very well stocked!"
United States
Sally O.
The price is £934
includes taxes & fees
21 Sept - 22 Sept
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

5. Glorious getaway on Portland's Eastern Promenade.

Glorious getaway on Portland's Eastern Promenade.
Munjoy Hill
9.8 out of 10, Exceptional, (183 reviews)
"Wonderful experience with exceptional hosts!"
United States
Cynthia
The price is £337
includes taxes & fees
1 Sept - 2 Sept
Glorious getaway on Portland's Eastern Promenade.

6. Waterfront Two Master Suite Penthouse with Rooftop

Waterfront Two Master Suite Penthouse with Rooftop
Downtown Portland
10.0 out of 10, Exceptional, (200 reviews)
"Great property. It was clean, comfortable, and the location was amazing"
United States
Jaylene G.
The price is £1,181
includes taxes & fees
7 Sept - 8 Sept
Waterfront Two Master Suite Penthouse with Rooftop

7. Spectacular Views & Comforts of Home in Portland s Most Desirable Neighborhood

Spectacular Views & Comforts of Home in Portland s Most Desirable Neighborhood
Munjoy Hill
10.0 out of 10, Exceptional, (19 reviews)
"Great host and very clean, comfortable stay! We all wished we would have had more time here and loved every bit of our stay. Sunrise on the rooftop deck, city lights up there at night. It was wonderful! We hope to return someday! "
United States
JESSICA S.
The price is £474
includes taxes & fees
7 Sept - 8 Sept
Spectacular Views & Comforts of Home in Portland s Most Desirable Neighborhood

8. Penthouse Two Master Waterfront Suite with Rooftop

Penthouse Two Master Waterfront Suite with Rooftop
Downtown Portland
10.0 out of 10, Exceptional, (267 reviews)
"This was one of the most spectacular places we have ever stayed. The views are amazing and the place is just incredible. We really look forward to our next visit!"
United States
Daryl R.
The price is £1,277
includes taxes & fees
29 Aug - 30 Aug
Penthouse Two Master Waterfront Suite with Rooftop

9. Downtown Penthouse Suite - Stunning Harbor Views

Downtown Penthouse Suite - Stunning Harbor Views
Downtown Portland
10.0 out of 10, Exceptional, (235 reviews)
"We loved it!"
United States
Joshua H.
The price is £939
includes taxes & fees
9 Sept - 10 Sept
Downtown Penthouse Suite - Stunning Harbor Views

10. Harborview - Curated East End Escape w/ Parking

Harborview - Curated East End Escape w/ Parking
Munjoy Hill
10.0 out of 10, Exceptional, (13 reviews)
"It was a beautiful property with everything you could need available. There were a lot of little touches that made it really nice! "
United States
Jeannette B.
The price is £722
includes taxes & fees
31 Aug - 1 Sept
Harborview - Curated East End Escape w/ Parking

11. 1200 Sq Ft ♦ West End Gem ♦ Perfect Location

1200 Sq Ft ♦ West End Gem ♦ Perfect Location
West End
9.2 out of 10, Wonderful, (105 reviews)
"Very nice place, clean, good location. On-street parking was available. Second floor kitchen & bath, so not for those with issues with stairs, but fine for us. Would stay again!"
United States
Gary
The price is £187
includes taxes & fees
31 Aug - 1 Sept
1200 Sq Ft ♦ West End Gem ♦ Perfect Location

12. Prime Old Port 3BR • Free Parking • Sleeps 8

Prime Old Port 3BR • Free Parking • Sleeps 8
Downtown Portland
9.8 out of 10, Exceptional, (164 reviews)
"Everything was great! Excellent location, clean and great communication. Thank you!"
United States
Stephanie W.
The price is £1,126
includes taxes & fees
12 Sept - 13 Sept
Prime Old Port 3BR • Free Parking • Sleeps 8

13. Arlie`s Digs! - One Block To Willard Beach!

Arlie`s Digs! - One Block To Willard Beach!
Willard Beach
10.0 out of 10, Exceptional, (69 reviews)
"Beautiful place, perfect location! "
United States
Melissa M.
The price is £450
includes taxes & fees
30 Aug - 31 Aug
Arlie`s Digs! - One Block To Willard Beach!

14. The Globe House on Munjoy Hill - Walk to Breweries

The Globe House on Munjoy Hill - Walk to Breweries
Munjoy Hill
10.0 out of 10, Exceptional, (102 reviews)
"Everything was as advertised; great accommodations!"
United States
Richard D.
The price is £517
includes taxes & fees
15 Sept - 16 Sept
The Globe House on Munjoy Hill - Walk to Breweries

15. Historic Home in the West End. Private Parking.

Historic Home in the West End. Private Parking.
West End
10.0 out of 10, Exceptional, (60 reviews)
"Perfect cozy apartment for a get away! Great location that’s walkable for shopping, brunch, and coffee and less than a 15 minute drive from everything else on our itinerary!"
United States
Callie R.
The price is £269
includes taxes & fees
7 Sept - 8 Sept
Historic Home in the West End. Private Parking.

16. Adorable Portland getaway on the Eastern Promenade

Adorable Portland getaway on the Eastern Promenade
Munjoy Hill
9.6 out of 10, Exceptional, (141 reviews)
"Owner was so accommodating!"
United States
Kiernan
The price is £233
includes taxes & fees
15 Sept - 16 Sept
Adorable Portland getaway on the Eastern Promenade

17. Peaceful & minutes from the Old Port with private parking

Peaceful & minutes from the Old Port with private parking
Knightville
9.8 out of 10, Exceptional, (11 reviews)
"Cute, convenient spot!"
United States
Kelly S.
The price is £287
includes taxes & fees
1 Sept - 2 Sept
Peaceful & minutes from the Old Port with private parking

18. Stylish Brownstone Downtown Free St|Perfect Getaway for 2

Stylish Brownstone Downtown Free St|Perfect Getaway for 2
Downtown Portland
10.0 out of 10, Exceptional, (44 reviews)
"Beautiful place, centrally located. Very comfortable all around."
United States
scott s.
The price is £322
includes taxes & fees
1 Sept - 2 Sept
Stylish Brownstone Downtown Free St|Perfect Getaway for 2

19. NEW 1 BDR-Heart of Munjoy Hill

NEW 1 BDR-Heart of Munjoy Hill
Munjoy Hill
9.8 out of 10, Exceptional, (7 reviews)
"Great location within walking distance to activities, food, the bay, etc. "
United States
Anne D.
The price is £395
includes taxes & fees
24 Aug - 25 Aug
NEW 1 BDR-Heart of Munjoy Hill

20. Incredible Location! Heart of Old Port/Spacious Apartment

Incredible Location! Heart of Old Port/Spacious Apartment
Downtown Portland
10.0 out of 10, Exceptional, (45 reviews)
"Great stay, beautiful place and perfect location. "
United States
Heather P.
The price is £1,334
includes taxes & fees
29 Aug - 30 Aug
Incredible Location! Heart of Old Port/Spacious Apartment
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, apart-hotels, 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 £134 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?

Long Island Retreat at Sunset Landing close to Portland, Maine: This highly rated holiday home rental in Long Island is located by the ocean, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals are there in Long Island?

With 5 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, or get outside and enjoy nature at Sand Beach. In the wider area, you’ll find Fifth Maine Museum and East End 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.