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

Long Island Vacation Rentals

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Check prices for these dates

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

Our top choices for Long Island vacation 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 ￥13,031
￥24,169 total
includes taxes & fees
Sep 17 - Sep 18
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 ￥13,845
￥24,983 total
includes taxes & fees
Sep 17 - Sep 18
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 ￥22,013
￥36,676 total
includes taxes & fees
Sep 20 - Sep 21
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 ￥21,664
￥72,457 total
includes taxes & fees
Sep 20 - Sep 21
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 ￥38,317
￥61,549 total
includes taxes & fees
Sep 23 - Sep 24
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 ￥22,959
￥40,074 total
includes taxes & fees
Oct 5 - Oct 6
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, (132 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 ￥36,999
￥64,679 total
includes taxes & fees
Sep 22 - Sep 23
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 ￥30,561
￥50,052 total
includes taxes & fees
Sep 22 - Sep 23
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 ￥28,156
￥57,238 total
includes taxes & fees
Sep 29 - Sep 30
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 ￥30,561
￥48,192 total
includes taxes & fees
Sep 27 - Sep 28
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 ￥26,062
￥79,081 total
includes taxes & fees
Oct 8 - Oct 9
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 ￥15,833
￥57,672 total
includes taxes & fees
Sep 20 - Sep 21
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 ￥36,691
￥78,547 total
includes taxes & fees
Sep 21 - Sep 22
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 ￥46,074
￥68,990 total
includes taxes & fees
Sep 20 - Sep 21
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, (112 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 ￥46,539
￥71,526 total
includes taxes & fees
Sep 27 - Sep 28
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 ￥32,670
￥68,752 total
includes taxes & fees
Sep 20 - Sep 21
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 ￥30,696
￥64,899 total
includes taxes & fees
Oct 5 - Oct 6
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 ￥53,365
￥87,083 total
includes taxes & fees
Oct 5 - Oct 6
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 traveler
The price is ￥42,971
￥67,129 total
includes taxes & fees
Sep 22 - Sep 23
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 ￥38,317
￥60,704 total
includes taxes & fees
Sep 20 - Sep 21
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

Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

10/10 Excellent
"Nice stay"
Shawna 2-night trip
Posted 3 hours ago
Clarion Hotel Portland Airport 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 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?

The Perfect Beach Escape: Cozy 4-Bedroom Retreat: Visitors like this Long Island vacation home rental. It is located on the beach and has a fireplace, a balcony, and a barbecue grill 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 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 East End Beach and Willard 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.