A calm sea with a sailboat and rocky coastline.

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Great Diamond Island vacation homes

A building named Willard Square with a storefront and a red vehicle parked outside.

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 AED 1,102
AED 2,220 total
includes taxes & fees
14 Oct - 15 Oct
Willard Square Family Home
A staircase with white railings and wooden steps leading to a dining area with a table and chairs.

2. 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, (61 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 417
AED 1,427 total
includes taxes & fees
29 Oct - 30 Oct
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
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, (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 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, (82 reviews)
"Everything was very well stocked!"
United States
Sally O.
The price is AED 2,562
AED 4,082 total
includes taxes & fees
5 Oct - 6 Oct
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
A two-story house with a balcony, a covered patio, and a fenced yard.

5. The Globe House on Munjoy Hill - Walk to Breweries

The Globe House on Munjoy Hill - Walk to Breweries
Munjoy Hill
10.0 out of 10, Exceptional, (109 reviews)
"Everything was as advertised; great accommodations!"
United States
Richard D.
The price is AED 1,363
AED 2,430 total
includes taxes & fees
6 Oct - 7 Oct
The Globe House on Munjoy Hill - Walk to Breweries
A restaurant window with 'OYSTER CO. EVENTIDE' signage, indicating a raw bar, chowders, and cocktails.

6. Modern & Sunny House Steps from the Promenade.

Modern & Sunny House Steps from the Promenade.
Munjoy Hill
10.0 out of 10, Exceptional, (44 reviews)
"Perfect stay for a quick trip to Portland! "
United States
stacey p.
The price is AED 1,074
AED 1,819 total
includes taxes & fees
5 Oct - 6 Oct
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.

7. 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, (20 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
28 Oct - 29 Oct
Spacious 4-bedroom house located in the heart of Portland, ME.
A snow-covered landscape with a house and a tree.

8. Serenity between the lakes and seashore

Serenity between the lakes and seashore
Westbrook
9.8 out of 10, Exceptional, (31 reviews)
"This is my second stay at this property and we have a third stay booked in the fall. Everything was perfect from ease of checking in and communication with the host to fully stocked kitchen and cleanliness. Highly recommend "
United States
Joanne N.
Serenity between the lakes and seashore
A spacious living area with a blue sofa, a coffee table, and a kitchen in the background.

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

New Luxury Maine Home Hot Tub, Fire Pit, Sleeps 10
North Deering
9.2 out of 10, Wonderful, (14 reviews)
"Very nice! Would stay again and would highly recommend."
United States
Peter H.
The price is AED 1,745
AED 3,246 total
includes taxes & fees
18 Oct - 19 Oct
New Luxury Maine Home Hot Tub, Fire Pit, Sleeps 10
An outdoor seating area with tables and benches in front of a building with a sign reading "BRAKES & SHOCKS Specialty Bakery".

10. 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 808
AED 2,606 total
includes taxes & fees
4 Oct - 5 Oct
Spacious Portland Home + Parking
A window with a view of a snowy landscape and bare trees.

11. Tranquility between the Lakes & Sea

Tranquility between the Lakes & Sea
Westbrook
The price is AED 420
AED 1,195 total
includes taxes & fees
5 Oct - 6 Oct
Tranquility between the Lakes & Sea
A two-story brick building with a front porch, a black door, and a window with a white frame.

12. 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 897
AED 2,230 total
includes taxes & fees
2 Nov - 3 Nov
The 87th Townhome - Local Landmark
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
9.4 out of 10, Exceptional, (11 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 386
AED 788 total
includes taxes & fees
4 Oct - 5 Oct
Mid Coast Getaway w/ water views
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.

14. 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 1,355
AED 3,471 total
includes taxes & fees
6 Oct - 7 Oct
Sleeps 16+ | W/D | Parking | 15 mins to Old Port
A compact kitchen with a dishwasher, microwave, and coffee maker on the countertop.

15. Quiet Spot in lovely Freeport neighborhood

Quiet Spot in lovely Freeport neighborhood
Freeport
The price is AED 440
AED 1,395 total
includes taxes & fees
11 Oct - 12 Oct
Quiet Spot in lovely Freeport neighborhood
A living room with a fireplace, leather sofa, and a chandelier.

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.
The price is AED 5,950
AED 9,701 total
includes taxes & fees
1 Nov - 2 Nov
Charming Historic Estate | In-town location
A lush garden with a hammock, a variety of flowers, and a lake in the background.

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 AED 1,616
AED 6,530 total
includes taxes & fees
3 Nov - 4 Nov
Classic New England Waterfront House Big Lawn Beautiful Sunrise
A spacious living room with a sofa, ottoman, and coffee table, a dining area with chairs, and a kitchen with cabinets and appliances.

18. 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.
The price is AED 1,711
AED 3,730 total
includes taxes & fees
7 Oct - 8 Oct
Luxe 5 Bed/ 3 Bath with Game Room & AC
A wooden deck with outdoor seating and string lights.

19. Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (71 reviews)
"The house was lovely and well kept and in a great location."
United States
Angela M.
The price is AED 744
AED 1,355 total
includes taxes & fees
5 Oct - 6 Oct
Full sized home
A spacious room with a wooden floor, a dining area with chairs and a table, a sofa, a TV, and a balcony with a view of the sea.

20. 2 bedroom w/ expansive water views

2 bedroom w/ expansive water views
West Point
10.0 out of 10, Exceptional, (5 reviews)
"Place was clean, beautiful and the photos do not do it justice. The perfect get away vacation from the rat race."
United States
Gregory M.
The price is AED 463
AED 884 total
includes taxes & fees
1 Nov - 2 Nov
2 bedroom w/ expansive water views
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 Regency Hotel & Spa

Portland Regency Hotel & Spa

10/10 Excellent
"Great staff - very nice folks all around !"
J. Forest 1-night trip
Posted 1 hour ago
Portland Regency Hotel & Spa

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