A calm sea with a sailboat and rocky coastline.

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Check prices for these dates

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

Our top choices for Great Diamond Island vacation homes

A staircase with white railings and wooden steps leading to a dining area with a table and chairs.

1. 1200 sq ft ♦ West End Townhouse ♦ Perfect Location

1200 sq ft ♦ West End Townhouse ♦ Perfect Location
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 AED 393
AED 1,398 total
includes taxes & fees
29 Nov - 30 Nov
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
A building named Willard Square with a storefront and a red vehicle parked outside.

2. 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 AED 1,315
AED 2,488 total
includes taxes & fees
12 Nov - 13 Nov
Willard Square Family Home
A living room with a sofa, coffee table, and a large rug. There is a dining area with chairs and a table. The room has a mural on the wall depicting a landscape.

3. 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 AED 702
AED 1,537 total
includes taxes & fees
11 Nov - 12 Nov
Chic 3-bedroom house in Munjoy Hill with off-street parking.
A storefront with the sign "OYSTERS" and a "RAW BAR" sign above the entrance.

4. Modern & Sunny House Steps from the Promenade.

Modern & Sunny House Steps from the Promenade.
Munjoy Hill
10.0 out of 10, Exceptional, (50 reviews)
"Perfect stay for a quick trip to Portland! "
United States
stacey p.
The price is AED 1,102
AED 1,866 total
includes taxes & fees
29 Nov - 30 Nov
Modern & Sunny House Steps from the Promenade.
A kitchen with a wooden island, black bar stools, a hanging light fixture, and a framed botanical print on the wall.

5. 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 AED 1,855
AED 3,339 total
includes taxes & fees
4 Nov - 5 Nov
Spacious 4-bedroom house located in the heart of Portland, ME.
A modern kitchen with dark cabinetry, stainless steel appliances, and a large island.

6. Gorgeous 3-bedroom house in charming Portland

Gorgeous 3-bedroom house in charming Portland
North Deering
9.0 out of 10, Wonderful, (4 reviews)
"This place was exactly as it looks in the photos. Really conveniently located with good amenities."
United States
Bridget M.
Gorgeous 3-bedroom house in charming Portland
A house with a wooden front door, a stone staircase, and a porch with a wooden railing.

7. 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 AED 2,565
AED 4,085 total
includes taxes & fees
1 Nov - 2 Nov
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
A wooden covered porch with a green door, potted plants, and a red watering can.

8. Charming West End Victorian

Charming West End Victorian
Parkside
The price is AED 838
AED 2,759 total
includes taxes & fees
30 Oct - 31 Oct
Charming West End Victorian
An outdoor seating area with tables and benches in front of a building with a sign reading "BRAKES & SHOCKS Specialty Bakery".

9. 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 AED 606
AED 2,358 total
includes taxes & fees
29 Nov - 30 Nov
Spacious Portland Home + Parking
A two-story brick building with a front porch, a black door, and a window with a white frame.

10. 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 AED 946
AED 2,324 total
includes taxes & fees
29 Nov - 30 Nov
The 87th Townhome by Everrow
A window with a view of a snowy landscape and bare trees.

11. Tranquility between the Lakes & Sea

Tranquility between the Lakes & Sea
Westbrook
9.4 out of 10, Exceptional, (3 reviews)
"Great location. Very nice place."
United States
Bernie G.
The price is AED 485
AED 1,293 total
includes taxes & fees
10 Nov - 11 Nov
Tranquility between the Lakes & Sea
Private kitchen

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

Steps to Old Port, balcony, private outdoor space
Downtown Portland
The price is AED 2,380
AED 4,704 total
includes taxes & fees
1 Nov - 2 Nov
Steps to Old Port, balcony, private outdoor space
A cozy living room with a wooden ceiling, a sofa, a table, and a sliding glass door leading to a balcony.

13. 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 AED 309
AED 700 total
includes taxes & fees
1 Nov - 2 Nov
Mid Coast Getaway w/ water views
A dining area with a wooden table and chairs, a red sofa, and a small round table with a decorative plate.

14. Quiet Spot in lovely Freeport neighborhood

Quiet Spot in lovely Freeport neighborhood
Freeport
The price is AED 520
AED 1,482 total
includes taxes & fees
2 Nov - 3 Nov
Quiet Spot in lovely Freeport neighborhood
A grassy area with a picnic table and chairs, a body of water, and two trees in the background.

15. 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 AED 634
AED 1,561 total
includes taxes & fees
16 Nov - 17 Nov
Orchid Harbor, Bailey Island 3BR
A two-story house with a stone staircase leading to a front door, surrounded by a garden with potted plants and a seating area with chairs.

16. 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.
Charming Historic Estate | In-town location
A light blue door with a numerical address sign, a doormat, and two wall-mounted lights.

17. Fabulous 3-bedroom house in Biddeford perfect for your beach getaway

Fabulous 3-bedroom house in Biddeford perfect for your beach getaway
Biddeford
10.0 out of 10, Exceptional, (1 review)
"This little house was absolutely charming! The owners were very accommodating and flexible with our dates and last minute booking. The house is incredibly cozy and the outdoor porch was a big hit. The location of this house is also amazing as you have access to the ocean, marsh and a beautiful pond. E would love to return with our grandkids who would love it! Thank you Shannon and Jim for sharing your special house with us!"
United States
Allison B.
The price is AED 367
AED 917 total
includes taxes & fees
31 Oct - 1 Nov
Fabulous 3-bedroom house in Biddeford perfect for your beach getaway
A modern living room with a teal sofa, two glasses of white wine, a tray of food, and a decorative candle on a wooden table.

18. Sleeps 16+ | W/D | Parking | 15 mins to Old Port

Sleeps 16+ | W/D | Parking | 15 mins to Old Port
Westbrook
10.0 out of 10, Exceptional, (1 review)
"This place was excellent, very clean, and the check-in/checkout process was very easy. The unit is broken into 3 distinct apartments with the upstairs being a one bedroom suite. However, all of the units are accessible to each other through stairs so it's convenient for staying connected while also having some separate space."
United States
damean s.
Sleeps 16+ | W/D | Parking | 15 mins to Old Port
A sunroom with a glass ceiling, outdoor seating, a hot tub, and a stone wall.

19. 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.
Coastal Retreat - Sauna, Hot Tub & Swim Spa - Near Beaches and Downtown Portland
A covered porch with a view of a lake and trees.

20. 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 AED 522
AED 1,433 total
includes taxes & fees
17 Nov - 18 Nov
Mere Point Sunrise Views at Eastern Shore!
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

Hilton Garden Inn Portland Downtown Waterfront

Hilton Garden Inn Portland Downtown Waterfront

10/10 Excellent
"Very comfortable stay. Friendly staff and comfortable beds. Location was perfect! Highly recommend"
Marcus 2-night trip
Posted 4 hours ago
Hilton Garden Inn Portland Downtown Waterfront

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