A calm sea with a sailboat and rocky coastline.

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Our top choices for Great Diamond Island vacation homes

1. 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 ¥56,736
¥101,830 total
includes taxes & fees
Nov 12 - Nov 13
Willard Square Family Home

2. Chic 3-bedroom house in Munjoy Hill with off-street parking.

Chic 3-bedroom house in Munjoy Hill with off-street parking.
Munjoy Hill
10.0 out of 10, Exceptional, (10 reviews)
"Wow, wow, wow! My family and I all agree that this has been the best rental home we have ever stayed in. The interior design is so chic, we were truly wowed by the attention to detail in this place. The beds and pillows are also extremely comfy, we all had a great two nights of sleep here. The location of this place is phenomenal, it neighbors the Portland Observatory, many bars/cafes, and is a short walk down to the eastern promenade. We will absolutely stay here again the next time we’re in...
United States
Maris P.
The price is ¥30,270
¥63,052 total
includes taxes & fees
Nov 11 - Nov 12
Chic 3-bedroom house in Munjoy Hill with off-street parking.

3. 1200 sq ft ♦ West End Townhouse ♦ Walk to Old Port

1200 sq ft ♦ West End Townhouse ♦ Walk to Old Port
West End
8.6 out of 10, Excellent, (64 reviews)
"Nice place, good location and very responsive host. I would definitely stay again when in Portland."
United States
Susan d.
The price is ¥15,032
¥55,425 total
includes taxes & fees
Nov 11 - Nov 12
1200 sq ft ♦ West End Townhouse ♦ Walk to Old Port

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.
The price is ¥111,253
¥168,252 total
includes taxes & fees
Nov 12 - Nov 13
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

5. 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 ¥49,465
¥83,912 total
includes taxes & fees
Nov 10 - Nov 11
Modern & Sunny East End House.

6. 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 ¥80,032
¥136,985 total
includes taxes & fees
Nov 10 - Nov 11
Spacious 4-bedroom house located in the heart of Portland, ME.

7. Charming West End Victorian

Charming West End Victorian
Parkside
The price is ¥37,471
¥114,778 total
includes taxes & fees
Dec 1 - Dec 2
Charming West End Victorian

8. Spacious Portland Home + Parking

Spacious Portland Home + Parking
Parkside
8.6 out of 10, Excellent, (4 reviews)
"we used the house has home base for several outings in Portland. Great location and easy parking."
United States
Ellen M.
The price is ¥26,149
¥96,563 total
includes taxes & fees
Nov 10 - Nov 11
Spacious Portland Home + Parking

9. The 87th Townhome by Everrow

The 87th Townhome by Everrow
West End
9.6 out of 10, Exceptional, (11 reviews)
"We had a wonderful time at the property! Super close walking distance to great shopping and restaurants. Host was so responsive and even checked in to make sure we were having a great stay. Would stay again!"
United States
Amy B.
The price is ¥33,717
¥86,847 total
includes taxes & fees
Nov 10 - Nov 11
The 87th Townhome by Everrow

10. Steps to Old Port, balcony, private outdoor space

Steps to Old Port, balcony, private outdoor space
Downtown Portland
The price is ¥106,499
¥201,246 total
includes taxes & fees
Nov 10 - Nov 11
Steps to Old Port, balcony, private outdoor space

11. Charming Historic Estate | In-town location

Charming Historic Estate | In-town location
West End
10.0 out of 10, Exceptional, (2 reviews)
"Steve was wonderful and readily available for any of our questions or just helpful recommendations! Made our stay so much more pleasurable!! We enjoyed 3 meals by their on staff chef. She also did an amazing job. We travel with 17 so needless to say it’s a lot but we had more than enough space for everyone. Also, have to mention the outdoor space was delightful!"
United States
shelley w.
The price is ¥298,259
¥446,886 total
includes taxes & fees
Nov 10 - Nov 11
Charming Historic Estate | In-town location

12. Fully Updated Airy Historic Home in South Freeport

Fully Updated Airy Historic Home in South Freeport
Freeport
10.0 out of 10, Exceptional, (1 review)
"Great property well kept and close to everything we wanted to do"
United States
boodu
The price is ¥22,663
¥73,071 total
includes taxes & fees
Nov 11 - Nov 12
Fully Updated Airy Historic Home in South Freeport

13. Quiet Spot in lovely Freeport neighborhood

Quiet Spot in lovely Freeport neighborhood
Freeport
The price is ¥17,102
¥52,079 total
includes taxes & fees
Nov 10 - Nov 11
Quiet Spot in lovely Freeport neighborhood

14. Orchid Harbor, Bailey Island 3BR

Orchid Harbor, Bailey Island 3BR
Harpswell
10.0 out of 10, Exceptional, (13 reviews)
"Lovely property, close to what we needed and wanted, host communicated promptly. Would definitely stay there again."
United States
Jane D.
The price is ¥19,433
¥55,448 total
includes taxes & fees
Nov 10 - Nov 11
Orchid Harbor, Bailey Island 3BR

15. Newly Renovated Luxury House with Game Room

Newly Renovated Luxury House with Game Room
Yarmouth
10.0 out of 10, Exceptional, (4 reviews)
"What a great place to stay! The home is very clean and very quiet. Our host was very responsive to any questions we had. We would book this one over and over again."
United States
Michelle T.
Newly Renovated Luxury House with Game Room

16. Coastal Retreat - Sauna, Hot Tub & Swim Spa - Near Beaches and Downtown Portland

Coastal Retreat - Sauna, Hot Tub & Swim Spa - Near Beaches and Downtown Portland
Scarborough
10.0 out of 10, Exceptional, (17 reviews)
"Great stay. Alexa was a great host. Having garaged parking and the indoor pool/hot tub was perfect for our stay that coincided with a snow. Would definitely stay here again next winter."
United States
Stuart R.
The price is ¥52,061
¥106,670 total
includes taxes & fees
Nov 10 - Nov 11
Coastal Retreat - Sauna, Hot Tub & Swim Spa - Near Beaches and Downtown Portland

17. Classic New England Waterfront House Big Lawn Beautiful Sunrise

Classic New England Waterfront House Big Lawn Beautiful Sunrise
Harpswell
10.0 out of 10, Exceptional, (2 reviews)
"We had a wonderful stay! "
United States
Ashma B.
The price is ¥55,468
¥241,495 total
includes taxes & fees
Nov 30 - Dec 1
Classic New England Waterfront House Big Lawn Beautiful Sunrise

18. Mid Coast Getaway w/ water views

Mid Coast Getaway w/ water views
West Point
9.2 out of 10, Wonderful, (12 reviews)
"The location and views from the cottage are quintessential coastal Maine. Small community with lobster pound and Maine Oyster Company across the street. John is a welcoming host and eager to make sure you enjoy your stay. The cottage is great for 2 people, equipped with the basics and has a great deck to enjoy the views. Planning to return next year. Great spot!"
United States
Rebecca
The price is ¥16,640
¥32,442 total
includes taxes & fees
Nov 12 - Nov 13
Mid Coast Getaway w/ water views

19. Mere Point Sunrise Views at Eastern Shore!

Mere Point Sunrise Views at Eastern Shore!
Brunswick
9.8 out of 10, Exceptional, (10 reviews)
"Lovely location "
United States
Michelle S.
The price is ¥19,900
¥55,915 total
includes taxes & fees
Nov 16 - Nov 17
Mere Point Sunrise Views at Eastern Shore!

20. Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (80 reviews)
"Wonderful stay!"
United States
Erika T.
The price is ¥31,696
¥55,105 total
includes taxes & fees
Nov 30 - Dec 1
Full sized home
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

Great Diamond Island Vacation Homes information

Number of reviews
379
Accommodation
599 Vacation Homes
Lowest Price
¥32,442
Highest Price
¥446,886

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