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 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Great Diamond Island vacation rentals

Honeymoon Studio | Egyptian cotton sheets, premium bedding, down comforters, bed sheets

1. 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
$357 nightly
The price is $389
Sep 6 - Sep 7
Total with taxes and fees
Fortland Island Campground
Property grounds

2. 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.
$430 nightly
The price is $468
Sep 8 - Sep 9
Total with taxes and fees
Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
TV

3. Private Entrance Residential Portland

Private Entrance Residential Portland
Deering Center
8.8 out of 10, Excellent, (11 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.
$165 nightly
The price is $166
Sep 7 - Sep 8
Total with taxes and fees
Private Entrance Residential Portland
Interior

4. 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, (27 reviews)
"Great place! We would definitely return if we were in the area."
United States
Preston
$270 nightly
The price is $294
Oct 5 - Oct 6
Total with taxes and fees
Charming Studio apartment with WiFi, AC in welcoming Portland
1 bedroom, WiFi, bed sheets

5. Studio Apartment near downtown Walkable!

Studio Apartment near downtown Walkable!
West Bayside
8.4 out of 10, Very Good, (17 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
$176 nightly
The price is $178
Sep 14 - Sep 15
Total with taxes and fees
Studio Apartment near downtown Walkable!
Interior

6. 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.
$305 nightly
The price is $332
Sep 16 - Sep 17
Total with taxes and fees
Willard Beach–Apartment Near Portland & Parks
Marina

7. Casco Bay Vista

Casco Bay Vista
East Deering
10.0 out of 10, Exceptional, (6 reviews)
"We had a great stay at Mat's place! Convenient location, very cute apartment with a lovely view of the water. Well equipped for a couple's weekend away. We appreciated the sharp knives for cooking and the comfy couch!"
United States
Charlotte B.
$374 nightly
The price is $407
Sep 14 - Sep 15
Total with taxes and fees
Casco Bay Vista
Smart TV

8. Beautiful 1st Floor Apartment & Amazing Shower

Beautiful 1st Floor Apartment & Amazing Shower
Parkside
8.8 out of 10, Excellent, (31 reviews)
"This was a clean and good location for our stay. "
United States
Jocelyn R.
$212 nightly
The price is $231
Sep 7 - Sep 8
Total with taxes and fees
Beautiful 1st Floor Apartment & Amazing Shower
Beach

9. 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.
$394 nightly
The price is $429
Sep 15 - Sep 16
Total with taxes and fees
City Amenities, Casco Bay Sunrises and Natural Beauty
Exterior

10. 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.
$423 nightly
The price is $461
Sep 6 - Sep 7
Total with taxes and fees
Ocean View East End Studio in a Historic Victorian
Dining

11. Furnished 1BR/1BA Walk to Maine Med/Mercy. Parking & All utilities included!

Furnished 1BR/1BA Walk to Maine Med/Mercy. Parking & All utilities included!
West End
9.2 out of 10, Wonderful, (10 reviews)
"Great place to stay - lovely building and really nicely kept, and it’s a perfect location if you want to walk down to Old Port, about 20 minutes. Would love to come back!"
United States
Cate
$419 nightly
The price is $457
Sep 9 - Sep 10
Total with taxes and fees
Furnished 1BR/1BA Walk to Maine Med/Mercy. Parking & All utilities included!
Interior

12. East end. Walk to food, beer and downtown fun.

East end. Walk to food, beer and downtown fun.
Munjoy Hill
9.8 out of 10, Exceptional, (42 reviews)
"Exactly as described and in one of the loveliest parts of Portland! Communication with owner was smooth and seamless. Perfect place to get to multiple places of interest in this charming city."
United States
Emily W.
$344 nightly
The price is $367
Sep 8 - Sep 9
Total with taxes and fees
East end. Walk to food, beer and downtown fun.
Interior

13. NEW 1 BDR-Heart of Munjoy Hill

NEW 1 BDR-Heart of Munjoy Hill
Munjoy Hill
9.8 out of 10, Exceptional, (8 reviews)
"Great location within walking distance to activities, food, the bay, etc. "
United States
Anne D.
$383 nightly
The price is $417
Oct 5 - Oct 6
Total with taxes and fees
NEW 1 BDR-Heart of Munjoy Hill
Interior

14. 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.
$344 nightly
The price is $375
Sep 20 - Sep 21
Total with taxes and fees
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
Flat-screen TV, Netflix, books, streaming services

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

Walk to Old Port ♦ West End Condo ♦ Parking
West End
9.6 out of 10, Exceptional, (90 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.
$379 nightly
The price is $413
Sep 7 - Sep 8
Total with taxes and fees
Walk to Old Port ♦ West End Condo ♦ Parking
Property grounds

16. Serenity between the lakes and seashore

Serenity between the lakes and seashore
Westbrook
9.8 out of 10, Exceptional, (30 reviews)
"This is my second stay at this property and we have a third stay booked in the fall. Everything was perfect from ease of checking in and communication with the host to fully stocked kitchen and cleanliness. Highly recommend "
United States
Joanne N.
$277 nightly
The price is $302
Sep 7 - Sep 8
Total with taxes and fees
Serenity between the lakes and seashore
Interior

17. Skyline 138: Charming West End Mansard Penthouse

Skyline 138: Charming West End Mansard Penthouse
Parkside
9.2 out of 10, Wonderful, (36 reviews)
"Good location; great space."
United States
Marie O.
$376 nightly
The price is $409
Sep 8 - Sep 9
Total with taxes and fees
Skyline 138: Charming West End Mansard Penthouse
Front of property

18. Evalina Hotel

Evalina Hotel
2.5 star property
Downtown Portland
10.0 out of 10, Exceptional, (11 reviews)
"Truly a wonderful place with an unbeatable location. Highly recommend for a visit to Portland."
United States
Eric
$635 nightly
The price is $692
Sep 7 - Sep 8
Total with taxes and fees
Evalina Hotel
Deluxe Suite, 1 King Bed | Private kitchen | Coffee/tea maker, full-size fridge, microwave, oven

19. The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (117 reviews)
"Really nice room and location"
United States
Victoria
$370 nightly
The price is $403
Sep 7 - Sep 8
Total with taxes and fees
The Weldon Hotel
Beach

20. Island View House BnB Self Check-In # 4 / Free Off-Street Parking

Island View House BnB Self Check-In # 4 / Free Off-Street Parking
Munjoy Hill
9.6 out of 10, Exceptional, (17 reviews)
"Loved the place! Very eclectic. Easy walk to downtown. Definitely will be back!"
United States
Cameron H.
$492 nightly
The price is $536
Sep 8 - Sep 9
Total with taxes and fees
Island View House BnB Self Check-In # 4 / Free Off-Street 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

Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

8/10 Good
"Hotel was great for a one night stay. The staff was friendly, though we didn’t interact with them much. Room was clean and beds + pillows were comfy. Wifi didn’t reach our room so that wasn’t great, breakfast was as expected. The back door on the first floor was broke and didn’t lock. Was definitely a safety concern. Easy drive in to Old Port. There was a spot to sit and smoke outside so that was pretty sweet!"
Ashley 1-night trip
Posted less than an hour ago
Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

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 $178 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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