A calm sea with a sailboat and rocky coastline.

Great Diamond Island Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Great Diamond Island vacation rentals

Deluxe Suite, 1 King Bed | Private kitchen | Coffee/tea maker, full-size fridge, microwave, oven

1. The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (118 reviews)
"Really nice room and location"
United States
Victoria
$469 nightly
The price is $504
Oct 1 - Oct 2
Total with taxes and fees
The Weldon Hotel
Front of property

2. 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
$651 nightly
The price is $709
Sep 13 - Sep 14
Total with taxes and fees
Evalina Hotel
Exterior

3. 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)
"Fantastic host, fantastic place, fantastic location. 30 second walk out to a massive green lawned park overlooking the water. Easy stroll downtown. Dan was a very friendly, welcoming, and accommodating host. We had a great stay and would return again."
United States
Ryan S.
$423 nightly
The price is $461
Sep 14 - Sep 15
Total with taxes and fees
Ocean View East End Studio in a Historic Victorian
Exterior detail

4. 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
$425 nightly
The price is $463
Sep 16 - Sep 17
Total with taxes and fees
Glorious getaway on Portland's Eastern Promenade.
Dining

5. 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.
$753 nightly
The price is $821
Sep 15 - Sep 16
Total with taxes and fees
Prime Old Port 3BR • Free Parking • Sleeps 8
Outdoor dining

6. The Globe House on Munjoy Hill - Walk to Breweries

The Globe House on Munjoy Hill - Walk to Breweries
Munjoy Hill
10.0 out of 10, Exceptional, (105 reviews)
"Everything was as advertised; great accommodations!"
United States
Richard D.
$591 nightly
The price is $644
Sep 15 - Sep 16
Total with taxes and fees
The Globe House on Munjoy Hill - Walk to Breweries
Interior

7. 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
$265 nightly
The price is $289
Oct 5 - Oct 6
Total with taxes and fees
Charming Studio apartment with WiFi, AC in welcoming Portland
Beach nearby

8. 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.
$832 nightly
The price is $906
Oct 1 - Oct 2
Total with taxes and fees
Arlie`s Digs! - One Block To Willard Beach!
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.
$376 nightly
The price is $409
Sep 22 - Sep 23
Total with taxes and fees
City Amenities, Casco Bay Sunrises and Natural Beauty
Outdoor dining

10. Modern & Sunny House Steps from the Promenade.

Modern & Sunny House Steps from the Promenade.
Munjoy Hill
10.0 out of 10, Exceptional, (43 reviews)
"Perfect stay for a quick trip to Portland! "
United States
stacey p.
$512 nightly
The price is $558
Oct 5 - Oct 6
Total with taxes and fees
Modern & Sunny House Steps from the Promenade.
TV

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

Hip & Luxurious Garden Retreat for Families, Foodies & Adventurers
Munjoy Hill
10.0 out of 10, Exceptional, (55 reviews)
"Everything from booking to checkout was outstanding! Very clean, great location, easy parking and walking to town. The host quickly communicates; highly recommend this place for your stay in Portland!"
United States
Kirsten Z.
$860 nightly
The price is $938
Sep 29 - Sep 30
Total with taxes and fees
Hip & Luxurious Garden Retreat for Families, Foodies & Adventurers
Marina

12. 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.
$372 nightly
The price is $405
Sep 15 - Sep 16
Total with taxes and fees
Casco Bay Vista
4 bedrooms, desk, iron/ironing board, travel crib

13. Industrial Farmhouse Chic in Portland`s Most Desirable Neighborhood

Industrial Farmhouse Chic in Portland`s Most Desirable Neighborhood
Munjoy Hill
9.8 out of 10, Exceptional, (43 reviews)
"Wonderful spacious condo for our family stay in Portland. Gracious and attentive hosts. Definitely recommend!"
United States
Kerry N.
$703 nightly
The price is $766
Sep 27 - Sep 28
Total with taxes and fees
Industrial Farmhouse Chic in Portland`s Most Desirable Neighborhood
Coffee/tea maker, fridge, microwave, oven

14. 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.
$912 nightly
The price is $994
Sep 15 - Sep 16
Total with taxes and fees
Harborview - Curated East End Escape w/ Parking
Interior

15. 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)
"Very comfortable and stocked well. Lacked for nothing and able to walk to most places. Host checked in which was very nice. Enjoyed Portland."
United States
sheila g.
$343 nightly
The price is $366
Sep 14 - Sep 15
Total with taxes and fees
East end. Walk to food, beer and downtown fun.
Beach

16. 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.
$491 nightly
The price is $535
Sep 29 - Sep 30
Total with taxes and fees
Island View House BnB Self Check-In # 4 / Free Off-Street Parking
Property grounds

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, (18 reviews)
"Great place with beautiful interiors Impeccably clean!"
United States
Janet S.
$582 nightly
The price is $634
Oct 6 - Oct 7
Total with taxes and fees
4br2ba House parking A Peaceful Oasis on Munjoy Hill
Coffee/tea maker, fridge, microwave, oven

18. East End Guesthouse

East End Guesthouse
Munjoy Hill
10.0 out of 10, Exceptional, (3 reviews)
"Fabulous stay!! Felt like we were living in a Crate & Barrel catalog. Great location. "
United States
Ashleigh F.
$477 nightly
The price is $520
Oct 7 - Oct 8
Total with taxes and fees
East End Guesthouse
Terrace/patio

19. 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, (31 reviews)
"Beautiful location with easy walk to downtown. "
United States
Megan T.
$657 nightly
The price is $716
Oct 4 - Oct 5
Total with taxes and fees
Portland’s Best Ocean Views from a 40-Foot Private Deck
Interior

20. NEW 1 BDR-Heart of Munjoy Hill

NEW 1 BDR-Heart of Munjoy Hill
Munjoy Hill
9.8 out of 10, Exceptional, (9 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
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Great Diamond Island Hotel Reviews

Holiday Inn Portland-By the Bay by IHG

Holiday Inn Portland-By the Bay by IHG

10/10 Excellent
"The hotel is a 10 to 15 minute walk to the waterfront and down town Parking in the garage is reasonably priced in and out is easy. The key system for the rooms, garage, elevators, entry doors has been upgraded from my previous stay and is excellent. Small frig in the room, microwave and ice down the hall, table and four chairs in the room make snacking easy."
Steven 2-night trip
Posted 1 hour ago
Holiday Inn Portland-By the Bay by IHG

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 $161 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.

Explore a world of travel with Expedia