A calm sea with a sailboat and rocky coastline.

Great Diamond Island Vacation Rentals

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Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Great Diamond Island vacation rentals

A bedroom with a wooden bed, a nightstand, a bench, a chair, and a ceiling with a light fixture.

1. Studio Apartment near downtown Walkable!

Studio Apartment near downtown Walkable!
West Bayside
8.2 out of 10, Very Good, (15 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
$166 nightly
The price is $167
Sep 1 - Sep 2
Total with taxes and fees
Studio Apartment near downtown Walkable!
A yurt with a bed, a desk, and a view of the outdoors.

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
$430 nightly
The price is $469
Sep 7 - Sep 8
Total with taxes and fees
Fortland Island Campground
A living room with a sofa, armchair, and glass coffee table. There are two lamps on side tables and a window with curtains.

3. Private Entrance Residential Portland

Private Entrance Residential Portland
Deering Center
8.6 out of 10, Excellent, (10 reviews)
$166 nightly
The price is $167
Sep 7 - Sep 8
Total with taxes and fees
Private Entrance Residential Portland
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, (5 reviews)
"Excellent in every way."
United States
Robert B.
$323 nightly
The price is $352
Sep 16 - Sep 17
Total with taxes and fees
Willard Beach–Apartment Near Portland & Parks
A modern house with a wooden exterior, a small garden, and a visible window.

5. 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, (39 reviews)
"Overall a pleasing stay."
United States
Mallory D.
$434 nightly
The price is $473
Aug 31 - Sep 1
Total with taxes and fees
Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
A staircase with white railings and wooden steps leading to a dining area with a table and chairs.

6. 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.
$334 nightly
The price is $364
Sep 3 - Sep 4
Total with taxes and fees
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
A kitchen with a wooden countertop, a black kettle, a vase with flowers, and a small wire basket.

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

Charming Studio apartment with WiFi, AC in welcoming Portland
Munjoy Hill
9.4 out of 10, Exceptional, (26 reviews)
"Great place! We would definitely return if we were in the area."
United States
Preston
$287 nightly
The price is $313
Sep 17 - Sep 18
Total with taxes and fees
Charming Studio apartment with WiFi, AC in welcoming Portland
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, (32 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
$300 nightly
The price is $327
Sep 1 - Sep 2
Total with taxes and fees
Sunny Spot with Private Parking.
A modern kitchen with a dining area, featuring a round table, chairs, and a hanging light fixture.

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

Elegant condo - walk to Portland's best restaurants & Old Port
East Bayside
9.4 out of 10, Exceptional, (83 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.
$471 nightly
The price is $513
Aug 31 - Sep 1
Total with taxes and fees
Elegant condo - walk to Portland's best restaurants & Old Port
A living room with a television, a wooden chest, a glass coffee table, a sofa, and a chair.

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, (89 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.
$347 nightly
The price is $378
Sep 7 - Sep 8
Total with taxes and fees
Walk to Old Port ♦ West End Condo ♦ Parking
A harbor with boats docked, a pier, and buildings in the background.

11. Casco Bay Vista

Casco Bay Vista
East Deering
10.0 out of 10, Exceptional, (4 reviews)
"Our stay was very comfortable; beautiful view from our deck. Mat was great with communication and the atmosphere was a perfect fit for us. We highly recommend for your stay in Portland."
United States
Susan R.
$406 nightly
The price is $443
Sep 14 - Sep 15
Total with taxes and fees
Casco Bay Vista
A building with a sign for "The Send Brewing Co." and a logo featuring a stylized tree.

12. 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, (12 reviews)
"Cute, convenient spot!"
United States
Kelly S.
$356 nightly
The price is $388
Aug 30 - Aug 31
Total with taxes and fees
Peaceful & minutes from the Old Port with private parking
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.
$587 nightly
The price is $640
Aug 30 - Aug 31
Total with taxes and fees
Arlie`s Digs! - One Block To Willard Beach!
A grand room with ornate chandeliers, a fireplace, and classical furniture.

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

Historic Home in the West End. Private Parking.
West End
10.0 out of 10, Exceptional, (61 reviews)
"This spot was perfect. So cute and very well-kept. Easy to get in and navigate."
United States
Anonymous traveler
$345 nightly
The price is $376
Sep 7 - Sep 8
Total with taxes and fees
Historic Home in the West End. Private Parking.
A spacious living room with large windows, a sofa, a chair, and a small table.

15. 1 Mi to Maine Street! MCM-Style Home in Brunswick

1 Mi to Maine Street! MCM-Style Home in Brunswick
Brunswick
9.6 out of 10, Exceptional, (11 reviews)
"Quiet, clean, well appointed house close to Maine St Brunswick and convenient to both Portland and points north. "
United States
Kendra G.
$255 nightly
The price is $278
Sep 23 - Sep 24
Total with taxes and fees
1 Mi to Maine Street! MCM-Style Home in Brunswick
A modern kitchen with a central island, bar stools, a dining table, and a built-in oven.

16. The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (115 reviews)
"Really nice room and location"
United States
Victoria
$427 nightly
The price is $459
Sep 7 - Sep 8
Total with taxes and fees
The Weldon Hotel
A house with a wooden staircase leading to a door marked with the number 50.

17. 1200 Sq Ft ♦ West End Gem ♦ Perfect Location

1200 Sq Ft ♦ West End Gem ♦ Perfect Location
West End
9.2 out of 10, Wonderful, (106 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
$339 nightly
The price is $370
Sep 23 - Sep 24
Total with taxes and fees
1200 Sq Ft ♦ West End Gem ♦ Perfect Location

18. 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)
"Lovely home in a beautiful location and Dan is a fantastic host. Ask him about his hot sauce!"
United States
Elliott H.
$429 nightly
The price is $468
Aug 30 - Aug 31
Total with taxes and fees
Ocean View East End Studio in a Historic Victorian
A street lined with buildings, one with a red door and a sign that reads "MINATO".

19. 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
$431 nightly
The price is $470
Sep 1 - Sep 2
Total with taxes and fees
Glorious getaway on Portland's Eastern Promenade.
A modern kitchen with a central island, stainless steel appliances, and contemporary artwork.

20. A Peaceful Oasis on Munjoy Hill: 1st flr - 3BR + parking

A Peaceful Oasis on Munjoy Hill: 1st flr - 3BR + parking
Munjoy Hill
10.0 out of 10, Exceptional, (8 reviews)
"This apartment was perfect. Great location, spotlessly clean, very spacious rooms and comfortable beds. Thank you Ani for letting us stay in your lovely apartment. "
United States
Lauren
A Peaceful Oasis on Munjoy Hill: 1st flr - 3BR + 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 Great Diamond Island Hotel Reviews

Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

10/10 Excellent
"Unless they are booked solid. I ONLY stay at the regency over the last several years. Fourth floor roof deck suite market street side ftw! Cheers!"
Trevor 1-night trip
Posted 5 hours ago
Portland Regency Hotel & Spa

Find out more about Great Diamond Island

Everything you need to know about Great Diamond Island vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Great Diamond Island vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 Great Diamond Island vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Great Diamond Island vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Great Diamond Island. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Great Diamond Island in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $167 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Great Diamond Island rentals

At Expedia, we put the best Great Diamond Island vacation 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 Great Diamond 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 Great Diamond Island vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Great Diamond 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.

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