A sunset over a lake surrounded by dense forests and a distant shoreline.

Long Island Holiday Rentals

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Check prices for these dates

In two weeks
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Long Island holiday rentals

A living room with a sofa, armchair, and glass coffee table. There are two lamps on side tables and a window with curtains.

1. Private Entrance Residential Portland

Private Entrance Residential Portland
Deering Center
8.4 out of 10, Very good, (12 reviews)
"Place was fine, good amount of space, host was very nice"
United States
Jillian F.
The price is NZ$270
includes taxes & fees
16 Sept - 17 Sept
Private Entrance Residential Portland
A bedroom with a wooden bed, a nightstand, a bench, a chair, and a ceiling with a light fixture.

2. Studio Apartment near downtown Walkable!

Studio Apartment near downtown Walkable!
West Bayside
8.4 out of 10, Very good, (18 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 NZ$279
includes taxes & fees
17 Sept - 18 Sept
Studio Apartment near downtown Walkable!
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 NZ$347
includes taxes & fees
16 Sept - 17 Sept
Beautiful 1st Floor Apartment & Amazing Shower
A modern house with a wooden exterior, a small garden, and a visible window.

4. 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 NZ$808
includes taxes & fees
20 Sept - 21 Sept
Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
A building with a sign for "The Send Brewing Co." and a logo featuring a stylized tree.

5. 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 NZ$596
includes taxes & fees
16 Sept - 17 Sept
Peaceful & minutes from the Old Port with private parking
A kitchen with a wooden countertop, a black kettle, a vase with flowers, and a small wire basket.

6. 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, (28 reviews)
"Great place! We would definitely return if we were in the area."
United States
Preston
The price is NZ$388
includes taxes & fees
27 Sept - 28 Sept
Charming Studio apartment with WiFi, AC in welcoming Portland
A wooden bench on a rocky shore overlooking a calm body of water.

7. City Amenities, Casco Bay Sunrises and Natural Beauty

City Amenities, Casco Bay Sunrises and Natural Beauty
East Deering
9.8 out of 10, Exceptional, (131 reviews)
"Wonderful place! Owner very responsible! Would stay again! Great choice for place to stay away from home."
United States
Arlene L.
The price is NZ$723
includes taxes & fees
22 Sept - 23 Sept
City Amenities, Casco Bay Sunrises and Natural Beauty
A modern kitchen with a wooden countertop, a glass coffee table, and a built-in shelf with kitchenware.

8. Sunny Spot with Private Parking.

Sunny Spot with Private Parking.
Knightville
10.0 out of 10, Exceptional, (33 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 NZ$549
includes taxes & fees
23 Sept - 24 Sept
Sunny Spot with Private Parking.
A dining table with chairs, a potted plant, and decorative items.

9. Willard Beach–Apartment Near Portland & Parks

Willard Beach–Apartment Near Portland & Parks
Willard Beach
10.0 out of 10, Exceptional, (7 reviews)
"Excellent in every way."
United States
Robert B.
The price is NZ$644
includes taxes & fees
14 Oct - 15 Oct
Willard Beach–Apartment Near Portland & Parks
A street lined with buildings, one with a red door and a sign that reads "MINATO".

10. Adorable Portland getaway on the Eastern Promenade

Adorable Portland getaway on the Eastern Promenade
Munjoy Hill
9.6 out of 10, Exceptional, (146 reviews)
"Owner was so accommodating!"
United States
Kiernan
The price is NZ$532
includes taxes & fees
27 Sept - 28 Sept
Adorable Portland getaway on the Eastern Promenade
A modern kitchen with a dining area, featuring a round table, chairs, and a hanging light fixture.

11. 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, (84 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 NZ$864
includes taxes & fees
8 Oct - 9 Oct
Elegant condo - walk to Portland's best restaurants & Old Port
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 NZ$643
includes taxes & fees
20 Sept - 21 Sept
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
A beach with a wooden chair and a small building in the background.

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, (70 reviews)
"Beautiful place, perfect location! "
United States
Melissa M.
The price is NZ$1,005
includes taxes & fees
20 Sept - 21 Sept
Arlie`s Digs! - One Block To Willard Beach!
A street lined with buildings, one with a red door and a sign that reads "MINATO".

14. Glorious getaway on Portland's Eastern Promenade.

Glorious getaway on Portland's Eastern Promenade.
Munjoy Hill
9.8 out of 10, Exceptional, (184 reviews)
"Wonderful experience with exceptional hosts!"
United States
Cynthia
The price is NZ$708
includes taxes & fees
16 Sept - 17 Sept
Glorious getaway on Portland's Eastern Promenade.

15. Ocean View East End Studio in a Historic Victorian

Ocean View East End Studio in a Historic Victorian
Portland
10.0 out of 10, Exceptional, (111 reviews)
"Fantastic host, fantastic place, fantastic location. 30 second walk out to a massive green lawned park overlooking the water. Easy stroll downtown. Dan was a very friendly, welcoming, and accommodating host. We had a great stay and would return again."
United States
Ryan S.
The price is NZ$800
includes taxes & fees
16 Sept - 17 Sept
Ocean View East End Studio in a Historic Victorian
A room with a radiator, a vase with flowers, and two framed pictures on the wall.

16. Skyline 138: Charming West End Mansard Penthouse

Skyline 138: Charming West End Mansard Penthouse
Parkside
9.2 out of 10, Wonderful, (37 reviews)
"Good location; great space."
United States
Marie O.
The price is NZ$773
includes taxes & fees
20 Sept - 21 Sept
Skyline 138: Charming West End Mansard Penthouse
A room with a wooden floor, a round table, two chairs, a sofa, and a patterned rug.

17. NEW 1 BDR-Heart of Munjoy Hill

NEW 1 BDR-Heart of Munjoy Hill
Munjoy Hill
9.8 out of 10, Exceptional, (9 reviews)
"Great location within walking distance to activities, food, the bay, etc. "
United States
Anne D.
The price is NZ$715
includes taxes & fees
5 Oct - 6 Oct
NEW 1 BDR-Heart of Munjoy Hill
A restaurant window with 'OYSTER CO. EVENTIDE' signage, indicating a raw bar, chowders, and cocktails.

18. Modern & Sunny House Steps from the Promenade.

Modern & Sunny House Steps from the Promenade.
Munjoy Hill
10.0 out of 10, Exceptional, (43 reviews)
"Perfect stay for a quick trip to Portland! "
United States
stacey p.
The price is NZ$878
includes taxes & fees
16 Sept - 17 Sept
Modern & Sunny House Steps from the Promenade.
A grand room with ornate chandeliers, a fireplace, and classical furniture.

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

Historic Home in the West End. Private Parking.
West End
10.0 out of 10, Exceptional, (63 reviews)
"This spot was perfect. So cute and very well-kept. Easy to get in and navigate."
United States
Anonymous traveller
The price is NZ$752
includes taxes & fees
22 Sept - 23 Sept
Historic Home in the West End. Private Parking.
A modern bar area with a counter, stools, and hanging lights.

20. West End Bright Spot with Parking.

West End Bright Spot with Parking.
West End
10.0 out of 10, Exceptional, (23 reviews)
"The space was pristine, comfortable, homey with an excellent location situated to shops and restaurants. Jennifer was a welcoming and warm host and we had no issues at all during our stay!"
United States
Luke E.
The price is NZ$602
includes taxes & fees
16 Sept - 17 Sept
West End Bright Spot with 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
"Clean room, great location for the price (easily the most affordable hotel within easy 1ish mile walk of downtown), dogs allowed, no issues."
Eugene 2-night trip
Posted less than an hour ago
La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

Find out more about Long Island

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Long Island holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Long Island. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Long Island. Seeing all the best attractions is bound to make you fall in love with Long Island. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Long Island short-term rentals, that won’t be hard to do.

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.