Great Diamond Island Holiday Rentals

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Our top choices for Great Diamond Island holiday rentals

Aparthotel in Downtown Portland

The Weldon Hotel
4.5 star property
9.8 out of 10, Exceptional, (91 reviews)
"Loved this place and would definitely stay here next time we go back."
United States
Eleni
The price is AU$382
includes taxes & fees
17 Feb - 18 Feb
The Weldon Hotel

Holiday Home in West Point

Escape to Positive Outlook
10.0 out of 10, Exceptional, (3 reviews)
"The host was welcoming. The home was clean, comfortable and the views were outstanding. "
United States
Rachel K.
The price is AU$303
includes taxes & fees
20 Jan - 21 Jan
Escape to Positive Outlook
10.0 out of 10, Exceptional, (2 reviews)
"We didn’t get enough time to evaluate but from the short visit, we can say that this is the small paradise within the Main area. Best camp ground facilities we have ever seen or experienced. Looking forward to visit with friends and extended families as well. "
United States
Hrishi K.
The price is AU$536
includes taxes & fees
25 Jan - 26 Jan
Large, luxurious geodesic dome - 04

Apartment in Freeport

Studio Apartment in Freeport
2.0 star property
10.0 out of 10, Exceptional, (1 review)
"I could not have ask for a better place to stay for my winter holiday trip in Freeport, Maine. This studio apartment went above my expectations. The entire space was much larger than I thought it would be. From the entry downstairs & throughout the entire apartment, it was clean & well-kept. Kitchen is fully equipped, has adequate space for meal prep, and there is plenty of room around the table & kitchen counter for dining. The living room is a welcoming pleasant area, and there is ample space...
United States
Di W.
The price is AU$228
includes taxes & fees
3 Feb - 4 Feb
Studio Apartment in Freeport
2.0 star property
10.0 out of 10, Exceptional, (25 reviews)
"A great location to see Portland and surroundings. A very clean and nice place to stay. "
United States
Pam B.
The price is AU$311
includes taxes & fees
18 Jan - 19 Jan
Pine Point Beach private, quaint, charming studio.

Apartment in Knightville

Sunny Spot with Private Parking.
2.0 star property
9.8 out of 10, Exceptional, (25 reviews)
"Cute property.. also really suitable for long stay as the amenities were complete and near groceries and some restaurants and cafes.. convenient!"
United States
Giana
The price is AU$303
includes taxes & fees
15 Feb - 16 Feb
Sunny Spot with Private Parking.
9.6 out of 10, Exceptional, (128 reviews)
"Tidy place in a great location! "
United States
Mary M.
The price is AU$278
includes taxes & fees
18 Jan - 19 Jan
Adorable Portland getaway on the Eastern Promenade
8.4 out of 10, Very good, (7 reviews)
"The summary and the pictures shown are exactly what you’re going to get. The owner did a good job with the description, I "
United States
Alexandria T.
The price is AU$204
includes taxes & fees
19 Jan - 20 Jan
Studio Apartment near downtown Walkable!
10.0 out of 10, Exceptional, (225 reviews)
"Beautiful penthouse! Close to the harbor and all the shopping and restaurants. "
United States
Jessi F.
The price is AU$879
includes taxes & fees
19 Jan - 20 Jan
Downtown Penthouse Suite - Stunning Harbor Views
10.0 out of 10, Exceptional, (4 reviews)
" The place was wonderful!! Very peaceful and beautiful!! "
United States
Anonymous traveller
The price is AU$1,050
includes taxes & fees
17 Feb - 18 Feb
Waterfront Access with Kayaks, Private Deck and a Firepit
10.0 out of 10, Exceptional, (13 reviews)
"The apartment was very clean and well appointed with everything you might need. The host was very friendly and attentive and check in and check out were very simple. Any questions I had were answered promptly. I would definitely stay here again!"
United States
Diana T.
The price is AU$914
includes taxes & fees
18 Jan - 19 Jan
Step right out to the beach! Amazing location 7 min to Portland. Unit 4

Apartment in Downtown Saco

Saco/Old Orchard Beach Get Away
2.0 star property
10.0 out of 10, Exceptional, (4 reviews)
"The host responded quickly and with all the info I could have ever needed. I didn't try the hot tub, but the shower in unit 2 was fantastic. All around very comfortable and clean place that i will go back to."
United States
Paul N.
The price is AU$558
includes taxes & fees
25 Jan - 26 Jan
Saco/Old Orchard Beach Get Away
10.0 out of 10, Exceptional, (66 reviews)
"Perfect for our girls trip! Right outside portland with gorgeous views; Meghan was so very accommodating as well!"
United States
Allysa Z.
The price is AU$1,588
includes taxes & fees
22 Jan - 23 Jan
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
8.0 out of 10, Very good, (24 reviews)
"Was the perfect place to unwind. Close enough to walk to beach, restaurants and shops. Enjoyed our stay emensly!"
United States
Maria H.
The price is AU$325
includes taxes & fees
26 Jan - 27 Jan
Updated 2 BD cottage. 10 min walk to Pier & Beach sleeps 5
9.8 out of 10, Exceptional, (7 reviews)
"This well- appointed apartment was perfect for our stay in the Portland area. Jennifer was always quick to answer any questions. We would definitely recommend this listing."
United States
Lynn E.
The price is AU$324
includes taxes & fees
17 Feb - 18 Feb
Peaceful & minutes from the Old Port with private parking
10.0 out of 10, Exceptional, (1 review)
The price is AU$1,361
includes taxes & fees
19 Jan - 20 Jan
NEW! Gray Woodland Escape | Golf, Pool & Cinema
9.6 out of 10, Exceptional, (18 reviews)
"We had a great time and it’s an awesome place. Can’t wait to rebook for next year. "
United States
Robert D.
The price is AU$1,353
includes taxes & fees
16 Feb - 17 Feb
Charming Victorian beach house 5 bedrooms. 50 steps to the beach

Holiday Home in West Point

Fantastic Waterfront Views
9.6 out of 10, Exceptional, (14 reviews)
"The views are amazing! A very relaxing place to be, and the house was clean and comfortable. "
United States
Monika G.
The price is AU$405
includes taxes & fees
19 Jan - 20 Jan
Fantastic Waterfront Views

Holiday Home in South Portland

Modern Getaway by the Sea
10.0 out of 10, Exceptional, (2 reviews)
"Had a nice stay! House was great."
United States
Karen T.
The price is AU$791
includes taxes & fees
17 Feb - 18 Feb
Modern Getaway by the Sea
9.8 out of 10, Exceptional, (65 reviews)
"Everything was nice & perfectly described. Great quiet neighborhood loved my stay & so did my Dogs thank you for a lovely stay"
United States
Teresa M.
The price is AU$356
includes taxes & fees
18 Jan - 19 Jan
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach
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

Everything you need to know about Great Diamond Island holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Great Diamond Island holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Great Diamond Island holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Great Diamond Island holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Great Diamond Island holiday rentals we have selected for you start as low as AU$204 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Great Diamond Island rentals

At Expedia, we put the best Great Diamond Island holiday 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 holiday.

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.