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Long Island Vacation Rentals

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Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Long Island vacation rentals

1 bedroom, WiFi, bed sheets

1. Studio Apartment near downtown Walkable!

Studio Apartment near downtown Walkable!
West Bayside
8.2 out of 10, Very Good, (14 reviews)
"I will admit the location and surrounding areas are a bit sketchy, but, once inside, we felt super secure. There are multiple doors and gates with locks to ensure safety. Place was clean and had everything we needed for a quick stay."
United States
Krysta
The price is ￥16,739
￥28,707 total
includes taxes & fees
Aug 19 - Aug 20
Studio Apartment near downtown Walkable!
Honeymoon Studio | Egyptian cotton sheets, premium bedding, down comforters, bed sheets

2. Fortland Island Campground

Fortland Island Campground
1.0 star property
Portland
10.0 out of 10, Exceptional, (3 reviews)
"It was very quiet and liked the experience of staying in a camp like setting."
United States
leela srinivas
The price is ￥49,440
￥79,954 total
includes taxes & fees
Aug 23 - Aug 24
Fortland Island Campground
Property grounds

3. Spacious and Contemporary Condo in the Heart of Portland - Close to Beach

Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
East Bayside
8.8 out of 10, Excellent, (38 reviews)
"Overall a pleasing stay."
United States
Mallory D.
The price is ￥22,263
￥75,329 total
includes taxes & fees
Aug 31 - Sep 1
Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
Interior

4. Sunny Spot with Private Parking.

Sunny Spot with Private Parking.
Knightville
10.0 out of 10, Exceptional, (31 reviews)
"Cute property.. also really suitable for long stay as the amenities were complete and near groceries and some restaurants and cafes.. convenient!"
United States
Giana
The price is ￥31,386
￥52,098 total
includes taxes & fees
Sep 1 - Sep 2
Sunny Spot with Private Parking.
Exterior detail

5. 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 ￥16,561
￥40,975 total
includes taxes & fees
Aug 31 - Sep 1
1200 Sq Ft ♦ West End Gem ♦ Perfect Location
Dining

6. Elegant condo - walk to Portland's best restaurants & Old Port

Elegant condo - walk to Portland's best restaurants & Old Port
East Bayside
9.2 out of 10, Wonderful, (82 reviews)
"I had a wonderful week at this perfect place. Met my expectations and way more. So walkable all over Portland. I will be back. Thank you so very much."
United States
Margaret H.
The price is ￥26,766
￥81,738 total
includes taxes & fees
Aug 25 - Aug 26
Elegant condo - walk to Portland's best restaurants & Old Port
Deluxe Suite, 1 King Bed | Private kitchen | Coffee/tea maker, full-size fridge, microwave, oven

7. The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (111 reviews)
"Really nice room and location"
United States
Victoria
The price is ￥47,663
￥63,909 total
includes taxes & fees
Sep 1 - Sep 2
The Weldon Hotel
Interior

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

Charming Studio apartment with WiFi, AC in welcoming Portland
Munjoy Hill
9.6 out of 10, Exceptional, (24 reviews)
"Great place! We would definitely return if we were in the area."
United States
Preston
The price is ￥33,159
￥53,173 total
includes taxes & fees
Sep 17 - Sep 18
Charming Studio apartment with WiFi, AC in welcoming Portland
Interior

9. 1200 sq ft ♦ West End Townhouse ♦ Perfect Location

1200 sq ft ♦ West End Townhouse ♦ Perfect Location
West End
8.4 out of 10, Very Good, (61 reviews)
"Nice place. Good location."
United States
Rob M.
The price is ￥22,096
￥67,352 total
includes taxes & fees
Sep 3 - Sep 4
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
Flat-screen TV, Netflix, books, streaming services

10. Walk to Old Port ♦ West End Condo ♦ Parking

Walk to Old Port ♦ West End Condo ♦ Parking
West End
9.6 out of 10, Exceptional, (88 reviews)
"Host was very responsive, and helpful. Location is amazing for walking the city."
United States
Chris P.
The price is ￥20,743
￥64,983 total
includes taxes & fees
Sep 7 - Sep 8
Walk to Old Port ♦ West End Condo ♦ Parking
Exterior

11. 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 ￥47,796
￥74,500 total
includes taxes & fees
Aug 23 - Aug 24
Ocean View East End Studio in a Historic Victorian
Exterior detail

12. 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 ￥47,318
￥74,847 total
includes taxes & fees
Sep 1 - Sep 2
Glorious getaway on Portland's Eastern Promenade.
Outdoor dining

13. 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 ￥39,352
￥63,906 total
includes taxes & fees
Sep 1 - Sep 2
Peaceful & minutes from the Old Port with private parking
Exterior detail

14. Adorable Portland getaway on the Eastern Promenade

Adorable Portland getaway on the Eastern Promenade
Munjoy Hill
9.6 out of 10, Exceptional, (140 reviews)
"Owner was so accommodating!"
United States
Kiernan
The price is ￥31,406
￥50,045 total
includes taxes & fees
Sep 15 - Sep 16
Adorable Portland getaway on the Eastern Promenade
Interior

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 ￥36,188
￥59,950 total
includes taxes & fees
Sep 7 - Sep 8
Historic Home in the West End. Private Parking.
Dining

16. Furnished 1BR/1BA Walk to Maine Med/Mercy. Parking & All utilities included!

Furnished 1BR/1BA Walk to Maine Med/Mercy. Parking & All utilities included!
West End
9.6 out of 10, Exceptional, (7 reviews)
"All was great...clean and convenient."
United States
Krista P.
The price is ￥32,203
￥77,848 total
includes taxes & fees
Sep 9 - Sep 10
Furnished 1BR/1BA Walk to Maine Med/Mercy. Parking & All utilities included!
TV

17. Mid Coast Getaway w/ water views

Mid Coast Getaway w/ water views
West Point
9.6 out of 10, Exceptional, (7 reviews)
"Second time we have stay in this cottage. The perfect location for a Maine vacation. "
United States
chuck c.
The price is ￥27,620
￥48,317 total
includes taxes & fees
Aug 28 - Aug 29
Mid Coast Getaway w/ water views
Terrace/patio

18. Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (62 reviews)
"Wonderful stay!"
United States
Erika T.
The price is ￥32,283
￥58,822 total
includes taxes & fees
Aug 24 - Aug 25
Full sized home
House (2 Bedrooms) | Interior

19. 1 Mi to Maine Street! Mcm-style Home in Brunswick

1 Mi to Maine Street! Mcm-style Home in Brunswick
3.0 star property
Brunswick
1 Mi to Maine Street! Mcm-style Home in Brunswick
Exterior

20. Large suite/private bath/private entrance on quiet street near Thomas Bay

Large suite/private bath/private entrance on quiet street near Thomas Bay
Brunswick
10.0 out of 10, Exceptional, (163 reviews)
"Susan and Jeff were amazing hosts! There were so kind, thoughtful and welcoming. The suite was extremely spacious, well decorated and very comfortable. We were very close to the Air Show which was the reason for our trip. They gave us great instructions for a short cut to the airfield and amazing dinner recommendations. We could not have chosen a better place to stay. We highly recommend this place!"
United States
Asha
The price is ￥20,565
￥25,891 total
includes taxes & fees
Sep 2 - Sep 3
Large suite/private bath/private entrance on quiet street near Thomas Bay
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

The Westin Portland Harborview

The Westin Portland Harborview

8/10 Good
"Convient location is why I chose it. A 15 minute walk to downtown wharf with all it’s charming restaurants & bars. No need to drive. Room OK. Not 5-Star. All of Portland is Manhattan prices. Parked in public garage adjoining hotel. Green sign. Hotel charged me $38 for the one night of parking. Breakfast was included but not allowed dishes that include lobster.😀"
Brian 1-night trip
Posted 10 hours ago
The Westin Portland Harborview

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
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  • 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 vacation rentals in Long Island?

Yes, we have vacation rentals close to popular local attractions in Long Island, or you can choose a more remote option if you're looking for relaxation. 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 vacation home rentals that Long Island has to offer?

Long Island Retreat at Sunset Landing close to Portland, Maine: Visitors like this Long Island vacation home rental. It is located by the ocean and has a patio, a garden, and a barbecue grill 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 you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals are there in Long Island?

With 5 Expedia vacation rentals, you're sure 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 larger area, you’ll find Fifth Maine Museum and East End Beach.

What’s a vacation rental in Long Island like?

Vacation rentals are privately owned properties you can stay in for several days or longer in Long Island. Vacation rentals offer extras such as WiFi and washers and dryers so you'll have everything you need. If you're concerned about a sanitized environment, a vacation rental can offer a sense of safety away from shared hotel elevators and busy concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular choice for family trips.