Great Diamond Island Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Great Diamond Island vacation rentals

A modern kitchen with a central island, bar stools, a dining table, and a built-in oven.

1. The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (131 reviews)
"It was so spacious, kitchen area was well kept and they have QR codes to help travels understand how to use certain things"
United States
Branden
The price is CA $265
CA $395 total
includes taxes & fees
Dec 2 - Dec 3
The Weldon Hotel
A multi-story building with a stone facade, large windows, and a corner entrance.

2. Evalina Hotel

Evalina Hotel
2.5 star property
Downtown Portland
10.0 out of 10, Exceptional, (19 reviews)
"Truly a wonderful place with an unbeatable location. Highly recommend for a visit to Portland."
United States
Eric
The price is CA $333
CA $575 total
includes taxes & fees
Dec 7 - Dec 8
Evalina Hotel
A modern living room with a sofa, ottoman, coffee table, TV, and a lamp.

3. Willard By the Sea - 30 ft to the beach- 2nd floor

Willard By the Sea - 30 ft to the beach- 2nd floor
Willard
10.0 out of 10, Exceptional, (16 reviews)
"Fantastic beach location and comfortable unit equipped with air conditioning (essential during the heat wave that occurred during our stay). Clean rooms, good size and full kitchen; comfortable furnishings.Only caution is that this is a beach-side location and appears to have a bit of a price premium for that reason. It’s justified but only if you’re planning to make good use of the beach."
United States
Gerald B.
The price is CA $226
CA $682 total
includes taxes & fees
Nov 17 - Nov 18
Willard By the Sea - 30 ft to the beach- 2nd floor
A room with a white table, two chairs, a plant on a stool, and a white wall with a blue trim.

4. 2-bedroom apartment in Portland, ME with WiFi, AC. Enjoy your stay!

2-bedroom apartment in Portland, ME with WiFi, AC. Enjoy your stay!
Munjoy Hill
8.8 out of 10, Excellent, (3 reviews)
"Was right in the area we wanted and in a nice neighborhood. Would def stay again!"
United States
Amalia C.
The price is CA $301
CA $480 total
includes taxes & fees
Nov 10 - Nov 11
2-bedroom apartment in Portland, ME with WiFi, AC. Enjoy your stay!
A spacious living area with a wooden floor, a white sofa, and a dining table with chairs. There is a kitchen area with a metal cabinet and a hanging light fixture.

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

Arlie`s Digs! - One Block To Willard Beach!
Willard Beach
10.0 out of 10, Exceptional, (73 reviews)
"Great stay!"
United States
Jason M.
The price is CA $270
CA $611 total
includes taxes & fees
Nov 30 - Dec 1
Arlie`s Digs! - One Block To Willard Beach!
A house with a wooden front door, a stone staircase, and a porch with a wooden railing.

6. Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
East Deering
10.0 out of 10, Exceptional, (85 reviews)
"Absolutely perfect rental!Great location with an amazing view!"
United States
Mike G.
The price is CA $992
CA $1,500 total
includes taxes & fees
Nov 12 - Nov 13
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
A gray house with a black front door, white trim, and a number 70 sign.

7. 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, (64 reviews)
"The apartment is very comfortable with everything we needed We loved the quiet neighborhood and the location was really great within walking distance to both the beach area and downtown shops & restaurants."
United States
maureen
The price is CA $438
CA $648 total
includes taxes & fees
Nov 22 - Nov 23
Vintage Maine & Modern Convenience in Portlands Exclusive East End
A modern living room with a sofa, coffee table, and chairs, a kitchen with wooden cabinets, and large windows offering a view.

8. Harborview - Curated East End Escape w/ Parking

Harborview - Curated East End Escape w/ Parking
Munjoy Hill
10.0 out of 10, Exceptional, (14 reviews)
"5 star in every way"
United States
Doug F.
The price is CA $633
CA $1,023 total
includes taxes & fees
Nov 10 - Nov 11
Harborview - Curated East End Escape w/ Parking
A modern kitchen with a central island, a dining area with a sofa and chairs, and a living room with a colorful rug and plants.

9. Modern & Sunny East End House.

Modern & Sunny East End House.
Munjoy Hill
10.0 out of 10, Exceptional, (51 reviews)
"Perfect stay for a quick trip to Portland! "
United States
stacey p.
The price is CA $441
CA $747 total
includes taxes & fees
Nov 10 - Nov 11
Modern & Sunny East End House.
A garden with a stone wall, a small pond, and various plants.

10. 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, (22 reviews)
"Great house! Wonderful location with so many wonderful touches to make our stay so comfortable. We would definitely stay there again."
United States
Anonymous traveller
The price is CA $423
CA $734 total
includes taxes & fees
Nov 30 - Dec 1
4br2ba House parking A Peaceful Oasis on Munjoy Hill
A building named Willard Square with a storefront and a red vehicle parked outside.

11. Willard Square Family Home

Willard Square Family Home
Willard Beach
9.8 out of 10, Exceptional, (13 reviews)
"Thoroughly enjoyed this house! "
United States
David W.
The price is CA $506
CA $908 total
includes taxes & fees
Nov 12 - Nov 13
Willard Square Family Home
A modern kitchen with a central island, stainless steel appliances, and contemporary artwork.

12. A Peaceful Oasis on Munjoy Hill: 1st flr - 3BR + parking

A Peaceful Oasis on Munjoy Hill: 1st flr - 3BR + parking
Munjoy Hill
10.0 out of 10, Exceptional, (11 reviews)
"Great spot. Roomy. Close to shops and ferries. It had everything we needed to see Portland."
United States
Benton M.
The price is CA $279
CA $522 total
includes taxes & fees
Nov 10 - Nov 11
A Peaceful Oasis on Munjoy Hill: 1st flr - 3BR + parking
A room with two wicker chairs, a potted plant, and a view of a body of water and buildings through large windows with blinds.

13. 2-Bedroom Apartment Steps from Eastern Prom - Walk to Everything!

2-Bedroom Apartment Steps from Eastern Prom - Walk to Everything!
Munjoy Hill
10.0 out of 10, Exceptional, (6 reviews)
"Lovely clean property in a really great location. Walkable to town center! Perfect !"
United States
Anonymous traveller
The price is CA $223
CA $580 total
includes taxes & fees
Nov 10 - Nov 11
2-Bedroom Apartment Steps from Eastern Prom - Walk to Everything!
A staircase with a glass railing, a wooden floor, a door labeled 'B', and a small wooden table with shelves.

14. Peaceful Oasis on Munjoy Hill 2nd flr 3BR parking

Peaceful Oasis on Munjoy Hill 2nd flr 3BR parking
Munjoy Hill
9.8 out of 10, Exceptional, (7 reviews)
"Just perfect. Clean, very nicely furnished and decorated, well equipped apartment was everything we needed in an absolutely fantastic location. Owner was friendly and helpful and we loved our stay."
United States
juliet a.
The price is CA $311
CA $535 total
includes taxes & fees
Nov 16 - Nov 17
Peaceful Oasis on Munjoy Hill 2nd flr 3BR parking
A black console table with a mirror, a lamp, books, and a potted plant.

15. Peaceful & minutes from Old Port w/private parking

Peaceful & minutes from Old Port w/private parking
Knightville
9.8 out of 10, Exceptional, (13 reviews)
"Cute, convenient spot!"
United States
Kelly S.
The price is CA $171
CA $347 total
includes taxes & fees
Nov 10 - Nov 11
Peaceful & minutes from Old Port w/private parking
A modern kitchen with a built-in oven, a dining area with a yellow sofa, and a kitchen island.

16. Sunny Spot with Private Parking

Sunny Spot with Private Parking
Knightville
9.8 out of 10, Exceptional, (38 reviews)
"Great property. Cute place. Note that there are very steep steps to get into the place, which is a conveyed attic."
United States
Greg Z.
The price is CA $142
CA $289 total
includes taxes & fees
Nov 10 - Nov 11
Sunny Spot with Private Parking
A modern kitchen with a central island, two stools, skylights, and a view of the outdoors.

17. East End Guesthouse

East End Guesthouse
Munjoy Hill
10.0 out of 10, Exceptional, (7 reviews)
"Fabulous stay!! Felt like we were living in a Crate & Barrel catalog. Great location. "
United States
Ashleigh F.
The price is CA $352
CA $541 total
includes taxes & fees
Nov 17 - Nov 18
East End Guesthouse
A kitchen with a wooden island, black bar stools, a hanging light fixture, and a framed botanical print on the wall.

18. Spacious 4-bedroom house located in the heart of Portland, ME.

Spacious 4-bedroom house located in the heart of Portland, ME.
Munjoy Hill
10.0 out of 10, Exceptional, (23 reviews)
"Great space for our needs: three generations for a graduation weekend!"
United States
Matt H.
The price is CA $713
CA $1,221 total
includes taxes & fees
Nov 10 - Nov 11
Spacious 4-bedroom house located in the heart of Portland, ME.
A modern living room with a wooden dining table, chairs, a TV, and a bookshelf.

19. 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, (47 reviews)
"A great place to stay while exploring and visiting Portland! Great communication, easy process, and would definitely stay again if we visit Franklin"
United States
Jordan M.
The price is CA $300
CA $495 total
includes taxes & fees
Nov 12 - Nov 13
East end. Walk to food, beer and downtown fun.
A modern living room with a brown leather sofa, a wooden sliding door, and a framed artwork on the wall.

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

Hip & Luxurious Garden Retreat for Families, Foodies & Adventurers
Munjoy Hill
10.0 out of 10, Exceptional, (60 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.
The price is CA $760
CA $1,168 total
includes taxes & fees
Nov 10 - Nov 11
Hip & Luxurious Garden Retreat for Families, Foodies & Adventurers
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

A waterfront marina with boats docked, buildings with multiple windows, and a red building with a visible restaurant.
Hilton Garden Inn Portland Downtown Waterfront

Hilton Garden Inn Portland Downtown Waterfront

Hilton Garden Inn Portland Downtown Waterfront
Downtown Portland

10/10 Excellent

We had a great hotel experience
Canada
Stephane
Reviewed July 31, 2026
Hilton Garden Inn Portland Downtown Waterfront

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, cottages, cabins, villas... 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Great Diamond Island vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Great Diamond Island vacation rentals we have selected for you start as low as CA $141 per night. Entering your travel dates in the search wizard 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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