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

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
$360 nightly
The price is $393
Aug 23 - Aug 24
Total with taxes and fees
Fortland Island Campground
Deluxe Suite, 1 King Bed | Private kitchen | Coffee/tea maker, full-size fridge, microwave, oven

2. 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
$395 nightly
The price is $423
Sep 1 - Sep 2
Total with taxes and fees
The Weldon Hotel
Front of property

3. Evalina Hotel

Evalina Hotel
2.5 star property
Downtown Portland
10.0 out of 10, Exceptional, (9 reviews)
"Truly a wonderful place with an unbeatable location. Highly recommend for a visit to Portland."
United States
Eric
$683 nightly
The price is $744
Aug 31 - Sep 1
Total with taxes and fees
Evalina Hotel
Exterior

4. 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
Outdoor dining

5. 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)
"Cute, convenient spot!"
United States
Kelly S.
$351 nightly
The price is $383
Aug 9 - Aug 10
Total with taxes and fees
Peaceful & minutes from the Old Port with private parking
Exterior detail

6. Vintage Maine & Modern Convenience in Portlands Exclusive East End

Vintage Maine & Modern Convenience in Portlands Exclusive East End
Munjoy Hill
9.8 out of 10, Exceptional, (54 reviews)
"Great location. Short walk to Old Port and shops restaurants. Host was great"
United States
Jeff P.
$516 nightly
The price is $563
Aug 13 - Aug 14
Total with taxes and fees
Vintage Maine & Modern Convenience in Portlands Exclusive East End
Interior

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, (23 reviews)
"Great place! We would definitely return if we were in the area."
United States
Preston
$296 nightly
The price is $323
Aug 31 - Sep 1
Total with taxes and fees
Charming Studio apartment with WiFi, AC in welcoming Portland
Exterior detail

8. 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
Exterior detail

9. 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.
TV, books, stereo, offices

10. Spectacular Views & Comforts of Home in Portland s Most Desirable Neighborhood

Spectacular Views & Comforts of Home in Portland s Most Desirable Neighborhood
Munjoy Hill
10.0 out of 10, Exceptional, (19 reviews)
"Great host and very clean, comfortable stay! We all wished we would have had more time here and loved every bit of our stay. Sunrise on the rooftop deck, city lights up there at night. It was wonderful! We hope to return someday! "
United States
JESSICA S.
$498 nightly
The price is $543
Sep 7 - Sep 8
Total with taxes and fees
Spectacular Views & Comforts of Home in Portland s Most Desirable Neighborhood
Interior

11. 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
Terrace/patio

12. Portland’s Best Ocean Views from a 40-Foot Private Deck

Portland’s Best Ocean Views from a 40-Foot Private Deck
Munjoy Hill
9.6 out of 10, Exceptional, (29 reviews)
"Beautiful location with easy walk to downtown. "
United States
Megan T.
$714 nightly
The price is $778
Sep 1 - Sep 2
Total with taxes and fees
Portland’s Best Ocean Views from a 40-Foot Private Deck
Exterior

13. Willard Square Family Home

Willard Square Family Home
Willard Beach
9.8 out of 10, Exceptional, (11 reviews)
"Great location, close to Old Port. Great bakery/coffee and ice cream next door. House was clean and comfortable!"
United States
Steve S.
$571 nightly
The price is $604
Aug 23 - Aug 24
Total with taxes and fees
Willard Square Family Home
Smart TV

14. Eastbayside/Munjoy - Charming Downtown Escape

Eastbayside/Munjoy - Charming Downtown Escape
East Bayside
9.8 out of 10, Exceptional, (37 reviews)
"Very nice location, clean and comfortable!"
United States
Ryan R.
$824 nightly
The price is $898
Aug 14 - Aug 15
Total with taxes and fees
Eastbayside/Munjoy - Charming Downtown Escape
Outdoor dining

15. 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!
Dining

16. Prime Old Port 3BR • Free Parking • Sleeps 8

Prime Old Port 3BR • Free Parking • Sleeps 8
Downtown Portland
9.8 out of 10, Exceptional, (164 reviews)
"Everything was great! Excellent location, clean and great communication. Thank you!"
United States
Stephanie W.
$683 nightly
The price is $744
Aug 16 - Aug 17
Total with taxes and fees
Prime Old Port 3BR • Free Parking • Sleeps 8
Coffee/tea maker, fridge, microwave, oven

17. Harborview - Curated East End Escape w/ Parking

Harborview - Curated East End Escape w/ Parking
Munjoy Hill
10.0 out of 10, Exceptional, (12 reviews)
"It was a beautiful property with everything you could need available. There were a lot of little touches that made it really nice! "
United States
Jeannette B.
$914 nightly
The price is $996
Aug 31 - Sep 1
Total with taxes and fees
Harborview - Curated East End Escape w/ Parking
Property grounds

18. 4br2ba House parking A Peaceful Oasis on Munjoy Hill

4br2ba House parking A Peaceful Oasis on Munjoy Hill
Munjoy Hill
10.0 out of 10, Exceptional, (16 reviews)
"Ani was very friendly and communicative and the place was comfortable and inviting. We had a great stay!"
United States
Cristina Q.
$699 nightly
The price is $762
Sep 2 - Sep 3
Total with taxes and fees
4br2ba House parking A Peaceful Oasis on Munjoy Hill
TV

19. Hip & Luxurious Garden Retreat for Families, Foodies & Adventurers

Hip & Luxurious Garden Retreat for Families, Foodies & Adventurers
Munjoy Hill
10.0 out of 10, Exceptional, (53 reviews)
"We have stayed here multiple times and every time it’s amazing!"
United States
Erica L.
$795 nightly
The price is $866
Sep 1 - Sep 2
Total with taxes and fees
Hip & Luxurious Garden Retreat for Families, Foodies & Adventurers
Smart TV

20. Newly Renovated 2nd Floor Apt near USM

Newly Renovated 2nd Floor Apt near USM
Oakdale
10.0 out of 10, Exceptional, (17 reviews)
"Per the title great location, cleanliness as advertised."
United States
Edub
$599 nightly
The price is $653
Aug 9 - Aug 10
Total with taxes and fees
Newly Renovated 2nd Floor Apt near USM
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

HomeAwhile

HomeAwhile

8/10 Good
"Well outfitted apartment style room"
geoffrey 1-night trip
Posted less than an hour ago
HomeAwhile

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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