Great Diamond Island Holiday Rentals from NZ$369: Search Short-Term Rentals

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Great Diamond Island holiday rentals

A modern kitchen with a central island, bar stools, a dining table, and a built-in oven.

1. The Weldon Hotel

Downtown Portland

Victoria

includes taxes & fees

2 Dec - 3 Dec

A multi-story building with a stone facade, large windows, and a corner entrance.

2. Evalina Hotel

Downtown Portland

Eric

includes taxes & fees

6 Dec - 7 Dec

A beach with clear water, people swimming, and houses in the background.

3. Willard By the Sea - 30 ft to the beach- 2nd floor

Willard

"Fantastic beach location and comfortable unit equipped with air conditioning (essential during the heat wave that occurred during our stay). Clean rooms, good size and full kitchen; comfortable furnishings.Only caution is that this is a beach-side location and appears to have a bit of a price premium for that reason. It’s justified but only if you’re planning to make good use of the beach."

Gerald B.

includes taxes & fees

17 Nov - 18 Nov

A room with a white table, two chairs, a plant on a stool, and a white wall with a blue trim.

4. 2-bedroom apartment in Portland, ME with WiFi, AC. Enjoy your stay!

Munjoy Hill

Amalia C.

includes taxes & fees

9 Nov - 10 Nov

A beach with a wooden chair and a small building in the background.

5. Arlie`s Digs! - One Block To Willard Beach!

Willard Beach

Jason M.

includes taxes & fees

30 Nov - 1 Dec

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

6. Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

East Deering

Mike G.

includes taxes & fees

12 Nov - 13 Nov

A gray house with a black front door, white trim, and a number 70 sign.

7. Vintage Maine & Modern Convenience in Portlands Exclusive East End

Munjoy Hill

maureen

includes taxes & fees

22 Nov - 23 Nov

A modern living room with a sofa, coffee table, and chairs, a kitchen with wooden cabinets, and large windows offering a view.

8. Harborview - Curated East End Escape w/ Parking

Munjoy Hill

Doug F.

includes taxes & fees

9 Nov - 10 Nov

A storefront with the sign 'OYSTERS' and a 'RAW BAR' sign above the entrance. There are outdoor seating areas with tables and chairs.

9. Modern & Sunny East End House.

Munjoy Hill

stacey p.

includes taxes & fees

9 Nov - 10 Nov

A garden with a stone wall, a small pond, and various plants.

10. 4br2ba House parking A Peaceful Oasis on Munjoy Hill

Munjoy Hill

Anonymous traveller

includes taxes & fees

30 Nov - 1 Dec

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

11. Willard Square Family Home

Willard Beach

David W.

includes taxes & fees

12 Nov - 13 Nov

A modern kitchen with a central island, stainless steel appliances, and contemporary artwork.

12. A Peaceful Oasis on Munjoy Hill: 1st flr - 3BR + parking

Munjoy Hill

Benton M.

includes taxes & fees

9 Nov - 10 Nov

A room with two wicker chairs, a potted plant, and a view of a body of water and buildings through large windows with blinds.

13. 2-Bedroom Apartment Steps from Eastern Prom - Walk to Everything!

Munjoy Hill

Anonymous traveller

includes taxes & fees

9 Nov - 10 Nov

A garden with a stone bridge over a small stream, surrounded by various plants and flowers.

14. Peaceful Oasis on Munjoy Hill 2nd flr 3BR parking

Munjoy Hill

juliet a.

includes taxes & fees

16 Nov - 17 Nov

15. Peaceful & minutes from Old Port w/private parking

Knightville

Kelly S.

includes taxes & fees

9 Nov - 10 Nov

16. Sunny Spot with Private Parking

Knightville

Greg Z.

includes taxes & fees

9 Nov - 10 Nov

A modern kitchen with a central island, two stools, skylights, and a view of the outdoors.

17. East End Guesthouse

Munjoy Hill

Ashleigh F.

includes taxes & fees

17 Nov - 18 Nov

A kitchen with a wooden island, black bar stools, a hanging light fixture, and a framed botanical print on the wall.

18. Spacious 4-bedroom house located in the heart of Portland, ME.

Munjoy Hill

Matt H.

includes taxes & fees

9 Nov - 10 Nov

A modern living room with a wooden dining table, chairs, a TV, and a bookshelf.

19. East end. Walk to food, beer and downtown fun.

Munjoy Hill

Jordan M.

includes taxes & fees

12 Nov - 13 Nov

A modern living room with a brown leather sofa, a wooden sliding door, and a framed artwork on the wall.

20. Hip & Luxurious Garden Retreat for Families, Foodies & Adventurers

Munjoy Hill

Kirsten Z.

includes taxes & fees

10 Nov - 11 Nov

View all properties

Find holiday rentals that suit your style

Top Great Diamond Island Hotel Reviews

A view from a window overlooking a body of water with a distant shoreline, a vase with flowers, and a glass on a table.

The McKernan Inn

South Portland

10/10 Excellent

Andrea

An outdoor patio area with wicker furniture, string lights, and a barbecue grill.

Residence Inn by Marriott Portland Downtown/Waterfront

Downtown Portland

10/10 Excellent

Santo

A rooftop terrace with a modern outdoor seating area, a fire pit, and a view of the cityscape.

Cambria Hotel Portland Downtown-Old Port

Downtown Portland

10/10 Excellent

The two queen suites are very spacious plus we liked having a refrigerator, mini kitchen and coffee machine. Well located as it’s within walking distance of the wharf area, shops and many of the old port attractions. We were fortunate to get a free all day parking spot directly across the road and there seemed to be other spots available in other nearby streets. Better than paying $40 a day for valet parking.

Steven

An outdoor seating area with a fire feature, comfortable seating, and a view of a waterfront.

Canopy by Hilton Portland Waterfront

Downtown Portland

10/10 Excellent

Ross

A spacious lounge with leather seating, round tables, and large windows offering a view of a body of water and buildings.

The Westin Portland Harborview

Downtown Portland

10/10 Excellent

Jenna

A modern interior with a bar area, seating, and shelves with plants and books.

The Press Hotel, Marriott Autograph Collection

Downtown Portland

10/10 Excellent

Paul

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 favorite 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 depends 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 NZ$369 per night. Entering your travel dates in the search wizard you might find 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.

Explore a world of travel with Expedia

Activities in Portland
Standard Link for Activities in Portland

Great Diamond Island Holiday Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Great Diamond Island holiday rentals

1. The Weldon Hotel

2. Evalina Hotel

3. Willard By the Sea - 30 ft to the beach- 2nd floor

4. 2-bedroom apartment in Portland, ME with WiFi, AC. Enjoy your stay!

5. Arlie`s Digs! - One Block To Willard Beach!

6. Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

7. Vintage Maine & Modern Convenience in Portlands Exclusive East End

8. Harborview - Curated East End Escape w/ Parking

9. Modern & Sunny East End House.

10. 4br2ba House parking A Peaceful Oasis on Munjoy Hill

11. Willard Square Family Home

12. A Peaceful Oasis on Munjoy Hill: 1st flr - 3BR + parking

13. 2-Bedroom Apartment Steps from Eastern Prom - Walk to Everything!

14. Peaceful Oasis on Munjoy Hill 2nd flr 3BR parking

15. Peaceful & minutes from Old Port w/private parking

16. Sunny Spot with Private Parking

17. East End Guesthouse

18. Spacious 4-bedroom house located in the heart of Portland, ME.

19. East end. Walk to food, beer and downtown fun.

20. Hip & Luxurious Garden Retreat for Families, Foodies & Adventurers

Find holiday rentals that suit your style

Top Great Diamond Island Hotel Reviews

The McKernan Inn

10/10 Excellent

Find out more about Great Diamond Island

Great Diamond Island holiday rentals: An excellent choice for every season

How to find incredible deals on Great Diamond Island rentals

Explore a world of travel with Expedia