A calm sea with a sailboat and rocky coastline.

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Great Diamond Island vacation homes

A house with a wooden front door, a stone staircase, and a porch with a wooden railing.

1. 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, (82 reviews)
"Absolutely perfect rental!Great location with an amazing view!"
United States
Mike G.
The price is AED 2,562
AED 4,082 total
includes taxes & fees
18 Oct - 19 Oct
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
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 kitchen with a wooden island, black bar stools, a hanging light fixture, and a framed botanical print on the wall.

3. 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, (22 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
16 Nov - 17 Nov
Spacious 4-bedroom house located in the heart of Portland, ME.
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, (47 reviews)
"Perfect stay for a quick trip to Portland! "
United States
stacey p.
The price is AED 1,074
AED 1,831 total
includes taxes & fees
18 Oct - 19 Oct
Modern & Sunny House Steps from the Promenade.
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.

5. 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, (9 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.
Chic 3-bedroom house in Munjoy Hill with off-street parking.
A spacious living area with a blue sofa, a coffee table, and a kitchen in the background.

6. New Luxury Maine Home Hot Tub, Fire Pit, Sleeps 10

New Luxury Maine Home Hot Tub, Fire Pit, Sleeps 10
North Deering
9.4 out of 10, Exceptional, (16 reviews)
"The house was perfect for our week in Portland. New, great features in the home, lovely backyard and close to everything Portland"
United States
Patrick J.
The price is AED 1,521
AED 2,954 total
includes taxes & fees
18 Oct - 19 Oct
New Luxury Maine Home Hot Tub, Fire Pit, Sleeps 10
A staircase with white railings and wooden steps leading to a dining area with a table and chairs.

7. 1200 sq ft ♦ West End Townhouse ♦ Perfect Location

1200 sq ft ♦ West End Townhouse ♦ Perfect Location
West End
8.4 out of 10, Very good, (63 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 354
AED 1,351 total
includes taxes & fees
20 Oct - 21 Oct
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
A kitchen with white cabinets, a radiator, and a dining area with a floral chair and a chessboard.

8. Charming West End Victorian

Charming West End Victorian
Parkside
Charming West End Victorian
A two-story brick building with a front porch, a black door, and a window with a white frame.

9. The 87th Townhome - Local Landmark

The 87th Townhome - Local Landmark
West End
9.4 out of 10, Exceptional, (9 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 797
AED 2,138 total
includes taxes & fees
2 Nov - 3 Nov
The 87th Townhome - Local Landmark
A dirt path in a park with autumn foliage.

10. WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres

WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres
Westbrook
9.6 out of 10, Exceptional, (43 reviews)
"Host was excellent, even thinking of bug spray, yoga mats, binoculars, and extra blankets. We loved our stay!"
United States
Genevieve W.
The price is AED 1,616
AED 2,310 total
includes taxes & fees
17 Oct - 18 Oct
WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres
An outdoor seating area with tables and benches in front of a building with a sign reading "BRAKES & SHOCKS Specialty Bakery".

11. 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.
Spacious Portland Home + Parking
A sunroom with a glass ceiling, outdoor seating, a hot tub, and a stone wall.

12. 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 AED 909
AED 2,216 total
includes taxes & fees
25 Oct - 26 Oct
Coastal Retreat - Sauna, Hot Tub & Swim Spa - Near Beaches and Downtown Portland
A living room with a fireplace, leather sofa, and a chandelier.

13. 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 spacious living room with a sofa, ottoman, and coffee table, a dining area with chairs, and a kitchen with cabinets and appliances.

14. Luxe 5 Bed/ 3 Bath with Game Room & AC

Luxe 5 Bed/ 3 Bath with Game Room & AC
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.
Luxe 5 Bed/ 3 Bath with Game Room & AC
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.

15. 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.
The price is AED 1,447
AED 3,799 total
includes taxes & fees
25 Oct - 26 Oct
Sleeps 16+ | W/D | Parking | 15 mins to Old Port
A room with a sliding glass door leading to an outdoor deck with Adirondack chairs and a table.

16. Three bedroom in United States of America, Freeport

Three bedroom in United States of America, Freeport
Freeport
10.0 out of 10, Exceptional, (13 reviews)
"All we could say was wow! Words cannot express the view from this house! It looked like a picture! Beautiful view, fully loaded kitchen, spacious, comfortable beds, everything was perfect. I have the worst cell service and I couldn’t get the app to work but David answered my call right away and helped us get in. I’d highly recommend this property and we can’t wait to come back!"
United States
Michael L.
The price is AED 1,337
AED 3,267 total
includes taxes & fees
8 Nov - 9 Nov
Three bedroom in United States of America, Freeport
A living room with a sofa, armchair, wooden coffee table, and a potted plant.

17. 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
Fully Updated Airy Historic Home in South Freeport
A grassy area with a picnic table and chairs, a body of water, and two trees in the background.

18. 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 653
AED 1,591 total
includes taxes & fees
28 Oct - 29 Oct
Orchid Harbor, Bailey Island 3BR
A window with a view of a snowy landscape and bare trees.

19. Tranquility between the Lakes & Sea

Tranquility between the Lakes & Sea
Westbrook
The price is AED 423
AED 1,210 total
includes taxes & fees
18 Oct - 19 Oct
Tranquility between the Lakes & Sea
A lush garden with a hammock, a variety of flowers, and a lake in the background.

20. 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 AED 1,616
AED 6,586 total
includes taxes & fees
3 Nov - 4 Nov
Classic New England Waterfront House Big Lawn Beautiful Sunrise
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

Clarion Pointe South Portland

Clarion Pointe South Portland

8/10 Good
"Comfortable beds. Refrigerator wasn’t very cold"
Lori 1-night trip
Posted 1 hour ago
Clarion Pointe South Portland

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