A calm sea with a sailboat and rocky coastline.

Great Diamond Island Vacation Rentals

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Our top choices for Great Diamond Island vacation rentals

1. The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (109 reviews)
"Really nice room and location"
United States
Victoria
$374 nightly
The price is $401
Sep 1 - Sep 2
Total with taxes and fees
The Weldon Hotel

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
$512 nightly
The price is $558
Sep 7 - Sep 8
Total with taxes and fees
Fortland Island Campground

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
$677 nightly
The price is $738
Aug 31 - Sep 1
Total with taxes and fees
Evalina Hotel

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

5. 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, (24 reviews)
"Great place! We would definitely return if we were in the area."
United States
Preston
$305 nightly
The price is $332
Sep 6 - Sep 7
Total with taxes and fees
Charming Studio apartment with WiFi, AC in welcoming Portland

6. Adorable Portland getaway on the Eastern Promenade

Adorable Portland getaway on the Eastern Promenade
Munjoy Hill
9.6 out of 10, Exceptional, (140 reviews)
"Owner was so accommodating!"
United States
Kiernan
$368 nightly
The price is $401
Aug 24 - Aug 25
Total with taxes and fees
Adorable Portland getaway on the Eastern Promenade

7. 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.

8. 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.
$502 nightly
The price is $547
Aug 16 - Aug 17
Total with taxes and fees
NEW 1 BDR-Heart of Munjoy Hill

9. 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, (11 reviews)
"Cute, convenient spot!"
United States
Kelly S.
$368 nightly
The price is $401
Sep 1 - Sep 2
Total with taxes and fees
Peaceful & minutes from the Old Port with private parking

10. Panoramic Water, Island & City Views w/Private Roof Deck

Panoramic Water, Island & City Views w/Private Roof Deck
Munjoy Hill
10.0 out of 10, Exceptional, (33 reviews)
"We had a super relaxing weekend! Great walks and proximity to restaurants. "
United States
Amy W.
$489 nightly
The price is $533
Aug 30 - Aug 31
Total with taxes and fees
Panoramic Water, Island & City Views w/Private Roof Deck

11. 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.
$690 nightly
The price is $752
Aug 16 - Aug 17
Total with taxes and fees
Prime Old Port 3BR • Free Parking • Sleeps 8

12. 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.
$494 nightly
The price is $538
Sep 7 - Sep 8
Total with taxes and fees
Spectacular Views & Comforts of Home in Portland s Most Desirable Neighborhood

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

Portland’s Best Ocean Views from a 40-Foot Private Deck
Munjoy Hill
9.4 out of 10, Exceptional, (30 reviews)
"Beautiful location with easy walk to downtown. "
United States
Megan T.
$713 nightly
The price is $777
Sep 1 - Sep 2
Total with taxes and fees
Portland’s Best Ocean Views from a 40-Foot Private Deck

14. Arlie`s Digs! - One Block To Willard Beach!

Arlie`s Digs! - One Block To Willard Beach!
Willard Beach
10.0 out of 10, Exceptional, (68 reviews)
"Beautiful place, perfect location! "
United States
Melissa M.
$625 nightly
The price is $681
Sep 7 - Sep 8
Total with taxes and fees
Arlie`s Digs! - One Block To Willard Beach!

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)
"Overall amazing experience! Property is beautifully maintained. Perfectly located, within walking distance from bakeries, pubs, and restraunts. Host was responsive and helpful."
United States
Jacqui B.
$535 nightly
The price is $583
Sep 1 - Sep 2
Total with taxes and fees
Modern & Sunny House Steps from the Promenade. Private Parking!

16. Harborview - Curated East End Escape w/ Parking

Harborview - Curated East End Escape w/ Parking
Munjoy Hill
10.0 out of 10, Exceptional, (13 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

17. 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

18. 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.
$881 nightly
The price is $960
Sep 10 - Sep 11
Total with taxes and fees
Hip & Luxurious Garden Retreat for Families, Foodies & Adventurers

19. 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

20. Stylish Brownstone Downtown Free St|Perfect Getaway for 2

Stylish Brownstone Downtown Free St|Perfect Getaway for 2
Downtown Portland
10.0 out of 10, Exceptional, (43 reviews)
"What a great stay! The rental property was absolutely fantastic! Can't wait to come back! Highly recommend staying here. "
United States
Ken C.
$697 nightly
The price is $760
Aug 21 - Aug 22
Total with taxes and fees
Stylish Brownstone Downtown Free St|Perfect Getaway for 2
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

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 $180 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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