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Long Island Holiday Rentals

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Long Island holiday rentals

A bedroom with a bed, a nightstand, a lamp, a door, and a staircase.

1. Great suburban location close to town!

Great suburban location close to town!
Deering Center
10.0 out of 10, Exceptional, (1 review)
"Small but cozy space, well kept, good value for the price and has all the amenities you could expect. Would be happy to stay here again."
United States
Peter H.
The price is AU$142
includes taxes & fees
25 Oct - 26 Oct
Great suburban location close to town!
A living room with a sofa, armchair, and glass coffee table. There are two lamps on side tables and a window with curtains.

2. Portland 1-bedroom with enclosed porch & parking

Portland 1-bedroom with enclosed porch & parking
Deering Center
8.2 out of 10, Very good, (15 reviews)
"As expected."
United States
Lance
The price is AU$162
includes taxes & fees
13 Oct - 14 Oct
Portland 1-bedroom with enclosed porch & parking
A living room with a sofa, armchairs, a coffee table, and a potted plant.

3. Beautiful 1st Floor Apartment & Amazing Shower

Beautiful 1st Floor Apartment & Amazing Shower
Parkside
9.0 out of 10, Wonderful, (32 reviews)
"This was a clean and good location for our stay. "
United States
Jocelyn R.
The price is AU$272
includes taxes & fees
27 Oct - 28 Oct
Beautiful 1st Floor Apartment & Amazing Shower
A dining table with chairs, a potted plant, and decorative items.

4. Willard Beach–Apartment Near Portland & Parks

Willard Beach–Apartment Near Portland & Parks
Willard Beach
10.0 out of 10, Exceptional, (9 reviews)
"Location and parking were perfect for our first visit to Portland"
United States
Linda
The price is AU$450
includes taxes & fees
27 Oct - 28 Oct
Willard Beach–Apartment Near Portland & Parks
A bedroom with a wooden bed, a nightstand, a bench, a chair, and a ceiling with a light fixture.

5. Studio Apartment near downtown Walkable!

Studio Apartment near downtown Walkable!
West Bayside
8.4 out of 10, Very good, (21 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 AU$219
includes taxes & fees
1 Nov - 2 Nov
Studio Apartment near downtown Walkable!
A kitchen with a wooden countertop, a black kettle, a vase with flowers, and a small wire basket.

6. Charming Studio Retreat with Queen bed, WiFi, and AC in welcoming Portland

Charming Studio Retreat with Queen bed, WiFi, and AC in welcoming Portland
Munjoy Hill
9.6 out of 10, Exceptional, (31 reviews)
"Loved this spot and would stay again. Had everything you needed and a great location. Cute little attic spot but nice and cool."
United States
Emily N.
The price is AU$334
includes taxes & fees
1 Nov - 2 Nov
Charming Studio Retreat with Queen bed, WiFi, and AC in welcoming Portland
A wooden house with a deck and a stone pathway leading to a grassy area.

7. Waterfront Couples Retreat w/Porch, Private Patio, Freeport, Near LL Bean

Waterfront Couples Retreat w/Porch, Private Patio, Freeport, Near LL Bean
Freeport
10.0 out of 10, Exceptional, (18 reviews)
"Hosts were very responsive with messages. The stay was clean and comfortable."
United States
Hana L.
The price is AU$324
includes taxes & fees
20 Oct - 21 Oct
Waterfront Couples Retreat w/Porch, Private Patio, Freeport, Near LL Bean
A modern house with a wooden exterior, a small garden, and a visible window.

8. 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, (40 reviews)
"Overall a pleasing stay."
United States
Mallory D.
The price is AU$662
includes taxes & fees
15 Oct - 16 Oct
Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
A street lined with buildings, one with a red door and a sign that reads "MINATO".

9. Adorable Portland getaway on the Eastern Promenade

Adorable Portland getaway on the Eastern Promenade
Munjoy Hill
9.6 out of 10, Exceptional, (152 reviews)
"Owner was so accommodating!"
United States
Kiernan
The price is AU$412
includes taxes & fees
20 Oct - 21 Oct
Adorable Portland getaway on the Eastern Promenade
A multi-story building with a stone facade, large windows, and a corner entrance.

10. Evalina Hotel

Evalina Hotel
2.5 star property
Downtown Portland
10.0 out of 10, Exceptional, (14 reviews)
"This is a very nice hotel in a great location. It’s new and wonderfully appointed. Everything about it is first class."
United States
Rick
The price is AU$748
includes taxes & fees
3 Nov - 4 Nov
Evalina Hotel
A black console table with a mirror above it, a lamp, and a potted plant beside it.

11. 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, (13 reviews)
"Cute, convenient spot!"
United States
Kelly S.
The price is AU$467
includes taxes & fees
3 Nov - 4 Nov
Peaceful & minutes from the Old Port with private parking
A staircase with white railings and wooden steps leading to a dining area with a table and chairs.

12. 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 and very responsive host. I would definitely stay again when in Portland."
United States
Susan d.
The price is AU$547
includes taxes & fees
20 Oct - 21 Oct
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
A cozy living room with a wooden ceiling, a sofa, a table, and a sliding glass door leading to a balcony.

13. Mid Coast Getaway w/ water views

Mid Coast Getaway w/ water views
West Point
9.2 out of 10, Wonderful, (12 reviews)
"The location and views from the cottage are quintessential coastal Maine. Small community with lobster pound and Maine Oyster Company across the street. John is a welcoming host and eager to make sure you enjoy your stay. The cottage is great for 2 people, equipped with the basics and has a great deck to enjoy the views. Planning to return next year. Great spot!"
United States
Rebecca
The price is AU$313
includes taxes & fees
1 Nov - 2 Nov
Mid Coast Getaway w/ water views
A modern kitchen with a wooden countertop, a glass coffee table, and a built-in shelf with kitchenware.

14. Sunny Spot with Private Parking.

Sunny Spot with Private Parking.
Knightville
10.0 out of 10, Exceptional, (35 reviews)
"This is a perfect location. 6 minutes from downtown Portland. Secure, Clean and Jen was a Perfect and attentive host. It is a hidden Gem!"
United States
Irish D.
The price is AU$458
includes taxes & fees
18 Oct - 19 Oct
Sunny Spot with Private Parking.
A beach with a wooden chair and a small building in the background.

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

Arlie`s Digs! - One Block To Willard Beach!
Willard Beach
10.0 out of 10, Exceptional, (70 reviews)
"Beautiful place, perfect location! "
United States
Melissa M.
The price is AU$661
includes taxes & fees
2 Nov - 3 Nov
Arlie`s Digs! - One Block To Willard Beach!
A modern kitchen with a dining area, featuring a round table, chairs, and a hanging light fixture.

16. 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, (85 reviews)
"It was nice if you like being right in town. There is no view and it's a bit noisy."
United States
Nancy S.
The price is AU$716
includes taxes & fees
8 Oct - 9 Oct
Elegant condo - walk to Portland's best restaurants & Old Port
A modern kitchen with a central island, bar stools, a dining table, and a built-in oven.

17. The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (123 reviews)
"Really nice room and location"
United States
Victoria
The price is AU$426
includes taxes & fees
2 Nov - 3 Nov
The Weldon Hotel
A house with a wooden staircase leading to a door marked with the number 50.

18. 1200 Sq Ft ♦ West End Gem ♦ Perfect Location

1200 Sq Ft ♦ West End Gem ♦ Perfect Location
West End
9.2 out of 10, Wonderful, (107 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 AU$395
includes taxes & fees
3 Nov - 4 Nov
1200 Sq Ft ♦ West End Gem ♦ Perfect Location
A two-story house with a covered porch, a garage, and a front yard with potted plants.

19. 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, (172 reviews)
"What a beautiful place to stay. Jeff and Susan made your stay a very special experience."
United States
DENESE
The price is AU$183
includes taxes & fees
3 Nov - 4 Nov
Large suite/private bath/private entrance on quiet street near Thomas Bay
A living room with a television, a wooden chest, a glass coffee table, a sofa, and a chair.

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

Walk to Old Port ♦ West End Condo ♦ Parking
West End
9.4 out of 10, Exceptional, (93 reviews)
"Was great for our few days in Portland! Having a designated parking space was great and the location was convenient for everything we wanted to do."
United States
Britney G.
The price is AU$528
includes taxes & fees
1 Nov - 2 Nov
Walk to Old Port ♦ West End Condo ♦ Parking
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

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

10/10 Excellent
"The room clean and the property was well kept. The included breakfast was solid for a hotel breakfast. My only complaints would be that we didnt have hand soap which took a few tries to track down because the desk staff was away when we came back late night, the other complaint is the elevator door is scary loud but it functions properly, just something wonky with the door"
Phillip 2-night trip
Posted 1 hour ago
La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

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, 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 favourite 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 depend 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 AU$214 per night. Entering your travel dates in the search wizard might find you 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?

The Perfect Beach Escape: Cozy 4-Bedroom Retreat: This holiday home rental outside of Long Island is located on the beach, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 4 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 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.