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
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

Our top choices for Great Diamond Island vacation rentals

1 bedroom, WiFi, bed sheets

1. Studio Apartment near downtown Walkable!

Studio Apartment near downtown Walkable!
West Bayside
8.2 out of 10, Very Good, (13 reviews)
"A perfectly decent place to stay, plenty of restaurants and bars within reasonable walking distance. Neighborhood is a bit rough, as the listing mentioned, but no problems while I was there. Response time on questions to the host could be better."
Canada
Brian
$176 nightly
The price is $178
Aug 11 - Aug 12
Total with taxes and fees
Studio Apartment near downtown Walkable!
Exterior detail

2. Adorable Portland getaway on the Eastern Promenade

Adorable Portland getaway on the Eastern Promenade
Munjoy Hill
9.6 out of 10, Exceptional, (139 reviews)
"Owner was so accommodating!"
United States
Kiernan
$287 nightly
The price is $313
Sep 6 - Sep 7
Total with taxes and fees
Adorable Portland getaway on the Eastern Promenade
Property grounds

3. 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, (38 reviews)
"Overall a pleasing stay."
United States
Mallory D.
$433 nightly
The price is $471
Aug 25 - Aug 26
Total with taxes and fees
Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
Interior

4. Sunny Spot with Private Parking.

Sunny Spot with Private Parking.
Knightville
10.0 out of 10, Exceptional, (31 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
$298 nightly
The price is $325
Sep 1 - Sep 2
Total with taxes and fees
Sunny Spot with Private Parking.
Interior

5. 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, (22 reviews)
"Great place! We would definitely return if we were in the area."
United States
Preston
$289 nightly
The price is $315
Aug 31 - Sep 1
Total with taxes and fees
Charming Studio apartment with WiFi, AC in welcoming Portland
Deluxe Suite, 1 King Bed | Private kitchen | Coffee/tea maker, full-size fridge, microwave, oven

6. The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (108 reviews)
"Really nice room and location"
United States
Victoria
$403 nightly
The price is $432
Sep 1 - Sep 2
Total with taxes and fees
The Weldon Hotel
Dining

7. 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, (81 reviews)
"I had a wonderful week at this perfect place. Met my expectations and way more. So walkable all over Portland. I will be back. Thank you so very much."
United States
Margaret H.
$471 nightly
The price is $513
Aug 23 - Aug 24
Total with taxes and fees
Elegant condo - walk to Portland's best restaurants & Old Port
Honeymoon Studio | Egyptian cotton sheets, premium bedding, down comforters, bed sheets

8. 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
$375 nightly
The price is $408
Aug 23 - Aug 24
Total with taxes and fees
Fortland Island Campground
Exterior detail

9. 1200 Sq Ft ♦ West End Gem ♦ Perfect Location

1200 Sq Ft ♦ West End Gem ♦ Perfect Location
West End
9.2 out of 10, Wonderful, (105 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
$259 nightly
The price is $282
Aug 31 - Sep 1
Total with taxes and fees
1200 Sq Ft ♦ West End Gem ♦ Perfect Location
Interior

10. 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."
United States
Rob M.
$422 nightly
The price is $460
Sep 3 - Sep 4
Total with taxes and fees
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
Exterior

11. Ocean View East End Studio in a Historic Victorian

Ocean View East End Studio in a Historic Victorian
Portland
9.8 out of 10, Exceptional, (108 reviews)
"Lovely view and accessibility to the Old Port area. Enjoyed our relaxing stay! Thanks Dan! "
United States
David E.
$429 nightly
The price is $468
Aug 23 - Aug 24
Total with taxes and fees
Ocean View East End Studio in a Historic Victorian
Flat-screen TV, Netflix, books, streaming services

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

Walk to Old Port ♦ West End Condo ♦ Parking
West End
9.6 out of 10, Exceptional, (88 reviews)
"It was what we were looking for- in Portland, with a parking spot. Some nice restaurants nearby- walking distance! Note the bathroom is on the first floor, bedrooms are on second. Modest but had everything we needed! What we were disappointed in was we had no idea how many museums and local attractions in a city are closed till the end of April or May! "
United States
Susan R.
$390 nightly
The price is $425
Sep 1 - Sep 2
Total with taxes and fees
Walk to Old Port ♦ West End Condo ♦ Parking
Exterior detail

13. Glorious getaway on Portland's Eastern Promenade.

Glorious getaway on Portland's Eastern Promenade.
Munjoy Hill
9.8 out of 10, Exceptional, (182 reviews)
"Wonderful experience with exceptional hosts!"
United States
Cynthia
$429 nightly
The price is $468
Sep 1 - Sep 2
Total with taxes and fees
Glorious getaway on Portland's Eastern Promenade.
Dining

14. Charming West End Hideaway. Private Parking

Charming West End Hideaway. Private Parking
West End
10.0 out of 10, Exceptional, (53 reviews)
"A wonderful stay with wonderful hosts. So cozy and quiet, not to mention charming. We will be back!"
United States
Anne G.
$349 nightly
The price is $380
Sep 1 - Sep 2
Total with taxes and fees
Charming West End Hideaway. Private Parking
Outdoor dining

15. Peaceful & minutes from the Old Port with private parking

Peaceful & minutes from the Old Port with private parking
Knightville
9.6 out of 10, Exceptional, (10 reviews)
"Jennifer’s VRBO is exactly as cute, clean and cozy as the listing’s photos depict. It is so well maintained that she has living house plants that are thriving 10/10. I can’t wait to stay again!"
United States
Liz P.
$366 nightly
The price is $399
Sep 4 - Sep 5
Total with taxes and fees
Peaceful & minutes from the Old Port with private parking
Beach nearby, sun loungers, beach towels

16. Charming Pine Point OOB Beach Cottage Tiny House, Steps away from the beach

Charming Pine Point OOB Beach Cottage Tiny House, Steps away from the beach
Grand Beach
9.8 out of 10, Exceptional, (53 reviews)
"Stay was good. It was clean well decorated and equipped with everything you need"
United States
Tom K.
$240 nightly
The price is $262
Aug 10 - Aug 11
Total with taxes and fees
Charming Pine Point OOB Beach Cottage Tiny House, Steps away from the beach
Interior

17. NEW 1 BDR-Heart of Munjoy Hill

NEW 1 BDR-Heart of Munjoy Hill
Munjoy Hill
9.8 out of 10, Exceptional, (7 reviews)
"Great location within walking distance to activities, food, the bay, etc. "
United States
Anne D.
$495 nightly
The price is $540
Aug 10 - Aug 11
Total with taxes and fees
NEW 1 BDR-Heart of Munjoy Hill
Outdoor dining

18. Modern & Sunny House Steps from the Promenade. Private Parking!

Modern & Sunny House Steps from the Promenade. Private Parking!
Munjoy Hill
10.0 out of 10, Exceptional, (42 reviews)
"Perfect stay for a quick trip to Portland! "
United States
stacey p.
$533 nightly
The price is $581
Sep 1 - Sep 2
Total with taxes and fees
Modern & Sunny House Steps from the Promenade. Private Parking!
Smart TV

19. Beautiful 1st Floor Apartment & Amazing Shower

Beautiful 1st Floor Apartment & Amazing Shower
Parkside
9.2 out of 10, Wonderful, (29 reviews)
"Apartment was as described. Clean, walking distort downtown and parks. Enjoyed stay. Easy communication with host. "
United States
James R.
$275 nightly
The price is $300
Aug 9 - Aug 10
Total with taxes and fees
Beautiful 1st Floor Apartment & Amazing Shower
Bar (on property)

20. West End Bright Spot with Parking.

West End Bright Spot with Parking.
West End
10.0 out of 10, Exceptional, (21 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.
$373 nightly
The price is $407
Sep 1 - Sep 2
Total with taxes and fees
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 Great Diamond Island Hotel Reviews

Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

10/10 Excellent
"Clean, comfortable and walking distance to Thompson's Point!"
Tina 1-night trip
Posted 1 hour ago
Clarion Hotel Portland Airport ME

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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