Long Island Holiday Rentals

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Check prices for these dates

In two weeks
22 May - 24 May
In two months
3 Jul - 5 Jul
In three months
31 Jul - 2 Aug
In four months
28 Aug - 30 Aug

Our top choices for Long Island holiday rentals

TV

Mid Coast Getaway w/ water views

Mid Coast Getaway w/ water views
West Point
9.2 out of 10, Wonderful, (5 reviews)
"Second time we have stay in this cottage. The perfect location for a Maine vacation. "
United States
chuck c.
The price is HK$987
HK$1,903 total
includes taxes & fees
18 May - 19 May
Mid Coast Getaway w/ water views
TV

2 bedroom w/ expansive water views

2 bedroom w/ expansive water views
West Point
10.0 out of 10, Exceptional, (3 reviews)
"Place was clean, beautiful and the photos do not do it justice. The perfect get away vacation from the rat race."
United States
Gregory M.
The price is HK$823
HK$1,655 total
includes taxes & fees
7 May - 8 May
2 bedroom w/ expansive water views
Terrace/patio

Camp Forever cottage

Camp Forever cottage
Harpswell
9.6 out of 10, Exceptional, (58 reviews)
"Everything was great, fantastic location!"
United States
Dennis H.
The price is HK$1,481
HK$2,639 total
includes taxes & fees
5 May - 6 May
Camp Forever cottage
3 bedrooms, WiFi, bed sheets

Fantastic Waterfront Views

Fantastic Waterfront Views
West Point
9.8 out of 10, Exceptional, (16 reviews)
"The location and views were incredible. Quiet and relaxing spot."
United States
Vanessa W.
The price is HK$1,234
HK$2,291 total
includes taxes & fees
5 May - 6 May
Fantastic Waterfront Views
Exterior

Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach

Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach
Brunswick
10.0 out of 10, Exceptional, (149 reviews)
"Lovely space, comfortable bed, very convenient to downtown Brunswick."
United States
Kimberly G.
The price is HK$705
HK$939 total
includes taxes & fees
24 May - 25 May
Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach
Smart TV

Pine Point Beach private, quaint, charming studio.

Pine Point Beach private, quaint, charming studio.
Blue Point
10.0 out of 10, Exceptional, (29 reviews)
"A great location to see Portland and surroundings. A very clean and nice place to stay. "
United States
Pam B.
The price is HK$1,128
HK$2,186 total
includes taxes & fees
5 May - 6 May
Pine Point Beach private, quaint, charming studio.
Outdoor dining

Modern, Luxurious, Cabin in the Woods - 17

Modern, Luxurious, Cabin in the Woods - 17
Freeport
10.0 out of 10, Exceptional, (3 reviews)
"Awesome camping in a great, quiet campground. The staff is very responsive and all the little details make this place special."
United States
Miranda K.
The price is HK$1,389
HK$2,411 total
includes taxes & fees
5 May - 6 May
Modern, Luxurious, Cabin in the Woods - 17
TV

Private Entrance Residential Portland

Private Entrance Residential Portland
Deering Center
8.8 out of 10, Excellent, (6 reviews)
"This was a great place to stay. Easy to get to all of our destinations. Place was clean and comfortable. Would stay here again. "
United States
Ameleah B.
The price is HK$535
HK$1,097 total
includes taxes & fees
5 May - 6 May
Private Entrance Residential Portland
Interior

Sunny Spot with Private Parking.

Sunny Spot with Private Parking.
Knightville
9.8 out of 10, Exceptional, (25 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 HK$952
HK$1,798 total
includes taxes & fees
5 May - 6 May
Sunny Spot with Private Parking.
Living area

Fred Cottage - Spacious retreat on Popham Beach!

Fred Cottage - Spacious retreat on Popham Beach!
Phippsburg
9.6 out of 10, Exceptional, (4 reviews)
"Off the beaten path, easy access to beach and Spinneys"
United States
Sean B.
Fred Cottage - Spacious retreat on Popham Beach!
Interior

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

Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach
Old Orchard Beach
9.8 out of 10, Exceptional, (68 reviews)
"Place was great and fenced in backyard for our dog. "
United States
Billy N.
The price is HK$987
HK$1,964 total
includes taxes & fees
5 May - 6 May
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach
Outdoor dining

Peaceful & minutes from the Old Port with private parking

Peaceful & minutes from the Old Port with private parking
Knightville
9.6 out of 10, Exceptional, (9 reviews)
"Great little place in south Portland! Close to many parks, lighthouses, and driving distance to downtown. Parking downtown and in the old port area can be tricky and expensive though. "
United States
Christopher R.
The price is HK$1,152
HK$2,169 total
includes taxes & fees
10 May - 11 May
Peaceful & minutes from the Old Port with private parking
Property grounds

Centerview cottage

Centerview cottage
Harpswell
9.6 out of 10, Exceptional, (59 reviews)
"Great spot to relax and enjoy the beautiful outdoors. Very quiet and amazing views of the water. Everything needed for a comfortable and relaxing getaway. Highly recommend if coming to the area! "
United States
Erin
The price is HK$2,311
HK$3,706 total
includes taxes & fees
5 May - 6 May
Centerview cottage
Smart TV

Willard Beach–Private Apt Near Portland & Parks

Willard Beach–Private Apt Near Portland & Parks
Willard Beach
10.0 out of 10, Exceptional, (5 reviews)
"Excellent in every way."
United States
Robert B.
The price is HK$1,371
HK$2,690 total
includes taxes & fees
28 May - 29 May
Willard Beach–Private Apt Near Portland & Parks
Beach nearby, sun-loungers, beach towels

Serene Pine Point Escape — 1 Block to Beach, Marsh Views & Portland

Serene Pine Point Escape — 1 Block to Beach, Marsh Views & Portland
Pine Point
9.6 out of 10, Exceptional, (37 reviews)
"Cute place; clean and inviting. Would happily stay again!"
United States
Kelly M.
The price is HK$797
HK$2,423 total
includes taxes & fees
11 May - 12 May
Serene Pine Point Escape — 1 Block to Beach, Marsh Views & Portland
2 bedrooms, WiFi, bed sheets

Large, luxurious geodesic dome - 04

Large, luxurious geodesic dome - 04
Freeport
10.0 out of 10, Exceptional, (2 reviews)
"We didn’t get enough time to evaluate but from the short visit, we can say that this is the small paradise within the Main area. Best camp ground facilities we have ever seen or experienced. Looking forward to visit with friends and extended families as well. "
United States
Hrishi K.
The price is HK$2,179
HK$3,477 total
includes taxes & fees
7 May - 8 May
Large, luxurious geodesic dome - 04
Exterior

Luxury on Back Cove - Three Gables

Luxury on Back Cove - Three Gables
Rosemont
10.0 out of 10, Exceptional, (9 reviews)
"GoodLocation, very clean. Would stay again "
United States
Carly B.
The price is HK$863
HK$2,768 total
includes taxes & fees
5 May - 6 May
Luxury on Back Cove - Three Gables
Fitness facility

HomeAwhile

HomeAwhile
2.0 star property
Scarborough
9.2 out of 10, Wonderful, (33 reviews)
"It was a perfect stay!"
United States
Armando
The price is HK$980
HK$1,068 total
includes taxes & fees
31 May - 1 Jun
HomeAwhile
Property grounds

Welcome to our BoHo Treehouse!

Welcome to our BoHo Treehouse!
Downtown Saco
9.8 out of 10, Exceptional, (9 reviews)
"Walkable to restaurants and shops and very easy process! "
United States
Meg B.
The price is HK$1,019
HK$2,161 total
includes taxes & fees
10 May - 11 May
Welcome to our BoHo Treehouse!
Interior

Downtown Brunswick New Look Old Charm Next to Bowdoin

Downtown Brunswick New Look Old Charm Next to Bowdoin
Brunswick
9.8 out of 10, Exceptional, (20 reviews)
"We really enjoyed our visit with family and friends and the location was perfect for what we needed. "
United States
Eliza
The price is HK$1,136
HK$2,570 total
includes taxes & fees
19 May - 20 May
Downtown Brunswick New Look Old Charm Next to Bowdoin
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

Aloft Portland Downtown Waterfront ME

Aloft Portland Downtown Waterfront ME

10/10 Excellent
"We enjoyed our stay at Aloft Portland Maine. The staff was very friendly and accomodating, and really loved our dog Enzo. Wonderful hotel."
Daniel 3-night trip
Posted 1 hour ago
Aloft Portland Downtown Waterfront ME

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?

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 6 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 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.