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
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Great Diamond Island vacation rentals

An outdoor seating area with two wicker chairs and a table, a large shade sail, and a view of the ocean.

1. City Amenities, Casco Bay Sunrises and Natural Beauty

City Amenities, Casco Bay Sunrises and Natural Beauty
East Deering
9.8 out of 10, Exceptional, (137 reviews)
"Wonderful place! Owner very responsible! Would stay again! Great choice for place to stay away from home."
United States
Arlene L.
City Amenities, Casco Bay Sunrises and Natural Beauty
A modern kitchen with a central island, bar stools, a dining table, and a built-in oven.

2. The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (128 reviews)
"Really nice room and location"
United States
Victoria
$263 nightly
The price is $280
Nov 16 - Nov 17
Total with taxes and fees
The Weldon Hotel
A multi-story building with a stone facade, large windows, and a corner entrance.

3. Evalina Hotel

Evalina Hotel
2.5 star property
Downtown Portland
10.0 out of 10, Exceptional, (16 reviews)
"This is a very nice hotel in a great location. It’s new and wonderfully appointed. Everything about it is first class."
United States
Rick
$367 nightly
The price is $400
Dec 1 - Dec 2
Total with taxes and fees
Evalina Hotel
A house with a wooden front door, a stone staircase, and a porch with a wooden railing.

4. 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.
$970 nightly
The price is $1,058
Nov 1 - Nov 2
Total with taxes and fees
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
A modern living room with a sofa, ottoman, coffee table, TV, and a lamp.

5. 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.
$497 nightly
The price is $522
Dec 1 - Dec 2
Total with taxes and fees
Willard By the Sea - 30 ft to the beach- 2nd floor
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.

6. 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.
$470 nightly
The price is $512
Nov 18 - Nov 19
Total with taxes and fees
Arlie`s Digs! - One Block To Willard Beach!
A kitchen with a wooden countertop, a black kettle, a vase with flowers, and a small wire basket.

7. Charming Studio Retreat with Queen bed, WiFi, and AC in welcoming Portland

Charming Studio Retreat with Queen bed, WiFi, and AC in welcoming Portland
Munjoy Hill
9.4 out of 10, Exceptional, (32 reviews)
"Had a wonderful stay. Very clean and great location."
United States
Aimee S.
$200 nightly
The price is $218
Nov 1 - Nov 2
Total with taxes and fees
Charming Studio Retreat with Queen bed, WiFi, and AC in welcoming Portland
A gray house with a black front door, white trim, and a number 70 sign.

8. 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, (63 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
$435 nightly
The price is $474
Nov 22 - Nov 23
Total with taxes and fees
Vintage Maine & Modern Convenience in Portlands Exclusive East End
A skylight with a view of a residential area, including houses and a body of water.

9. Island View House BnB Self Check-in # 3 / Free Parking

Island View House BnB Self Check-in # 3 / Free Parking
Munjoy Hill
10.0 out of 10, Exceptional, (15 reviews)
"Good amount of space for our family group, beautiful old house, updated and clean, super friendly hosts, great location for beach/pier area access."
United States
Denise D.
Island View House BnB Self Check-in # 3 / Free Parking
A building named Willard Square with a storefront and a red vehicle parked outside.

10. 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.
$606 nightly
The price is $643
Nov 12 - Nov 13
Total with taxes and fees
Willard Square Family Home
A room with a wooden floor, a round table, two chairs, a sofa, and a patterned rug.

11. NEW 1 BDR-Heart of Munjoy Hill

NEW 1 BDR-Heart of Munjoy Hill
Munjoy Hill
9.8 out of 10, Exceptional, (16 reviews)
"Fantastic little spot. Great location and easy to find parking even if not using what is reserve. Home had everything necessary for a stay. Hosts were prompt with communication."
United States
Susan
NEW 1 BDR-Heart of Munjoy Hill
A garden with a stone wall, a small pond, and various plants.

12. 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 traveler
$477 nightly
The price is $520
Nov 30 - Dec 1
Total with taxes and fees
4br2ba House parking A Peaceful Oasis on Munjoy Hill
A narrow hallway with wooden flooring and white walls.

13. 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.
$338 nightly
The price is $368
Nov 2 - Nov 3
Total with taxes and fees
A Peaceful Oasis on Munjoy Hill: 1st flr - 3BR + parking
A kitchen with a wooden island, black bar stools, a hanging light fixture, and a framed botanical print on the wall.

14. 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.
$793 nightly
The price is $864
Nov 4 - Nov 5
Total with taxes and fees
Spacious 4-bedroom house located in the heart of Portland, ME.
Living area

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.
$307 nightly
The price is $335
Nov 9 - Nov 10
Total with taxes and fees
Peaceful & minutes from Old Port w/private parking
A modern living room with a wooden dining table, chairs, a TV, and a bookshelf.

16. 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)
"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.
$329 nightly
The price is $350
Nov 1 - Nov 2
Total with taxes and fees
East end. Walk to food, beer and downtown fun.
Dining

17. 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.
$648 nightly
The price is $724
Dec 1 - Dec 2
Total with taxes and fees
Harborview - Curated East End Escape w/ Parking
A modern kitchen with a central island, two stools, skylights, and a view of the outdoors.

18. East End Guesthouse

East End Guesthouse
Munjoy Hill
10.0 out of 10, Exceptional, (6 reviews)
"Fabulous stay!! Felt like we were living in a Crate & Barrel catalog. Great location. "
United States
Ashleigh F.
$367 nightly
The price is $400
Nov 3 - Nov 4
Total with taxes and fees
East End Guesthouse
Living area

19. 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.
$296 nightly
The price is $323
Nov 4 - Nov 5
Total with taxes and fees
Sunny Spot with Private 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

Portland Harbor Hotel

Portland Harbor Hotel

10/10 Excellent
"Perfect location, beautiful hotel! Hotel was very clean and upscale. With a common coffee/tea/snack bar on each floor."
Jennifer 1-night trip
Posted 2 hours ago
Portland Harbor Hotel

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 $120 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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