Great Diamond Island Vacation Rentals from $68: Search Short-Term Rentals

A calm sea with a sailboat and rocky coastline.

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Our top choices for Great Diamond Island vacation rentals

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

1. The Weldon Hotel

Downtown Portland

Branden

$261 nightly

Dec 1 - Dec 2

Total with taxes and fees

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

2. Evalina Hotel

Downtown Portland

Eric

$354 nightly

Dec 13 - Dec 14

Total with taxes and fees

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.

$392 nightly

Nov 17 - Nov 18

Total with taxes and fees

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.

$310 nightly

Nov 13 - Nov 14

Total with taxes and fees

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.

$390 nightly

Nov 30 - Dec 1

Total with taxes and fees

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.

$925 nightly

Nov 16 - Nov 17

Total with taxes and fees

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

Aaron S.

$431 nightly

Nov 22 - Nov 23

Total with taxes and fees

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.

$618 nightly

Nov 15 - Nov 16

Total with taxes and fees

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.

$454 nightly

Nov 15 - Nov 16

Total with taxes and fees

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 traveler

$475 nightly

Nov 30 - Dec 1

Total with taxes and fees

A backyard with a table and four chairs, surrounded by a wooden fence and trees.

11. Willard Square Family Home

Willard Beach

David W.

$578 nightly

Nov 15 - Nov 16

Total with taxes and fees

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.

$324 nightly

Nov 16 - Nov 17

Total with taxes and fees

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 traveler

$375 nightly

Nov 18 - Nov 19

Total with taxes and fees

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.

$347 nightly

Nov 16 - Nov 17

Total with taxes and fees

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

Knightville

Kelly S.

$215 nightly

Nov 15 - Nov 16

Total with taxes and fees

16. Sunny Spot with Private Parking

Knightville

Greg Z.

$181 nightly

Nov 15 - Nov 16

Total with taxes and fees

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

17. East End Guesthouse

Munjoy Hill

Ashleigh F.

$349 nightly

Nov 17 - Nov 18

Total with taxes and fees

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.

$793 nightly

Nov 13 - Nov 14

Total with taxes and fees

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.

$316 nightly

Nov 15 - Nov 16

Total with taxes and fees

A bedroom with a bed, bedside table, chair, and a large window.

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

Munjoy Hill

Kirsten Z.

$723 nightly

Nov 15 - Nov 16

Total with taxes and fees

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Top Great Diamond Island Hotel Reviews

A spacious lobby with multiple seating areas, a fireplace, and large windows.

Embassy Suites by Hilton Portland Maine

Portland

10/10 Excellent

Michael

Inn On Peaks Island

Peaks Island

10/10 Excellent

Devon

A modern bar area with a wooden bar counter, black bar stools, and a contemporary light fixture.

AC Hotel Portland Downtown/Waterfront, ME

Downtown Portland

10/10 Excellent

Craig

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

seth

A balcony with a table and chairs, overlooking a street with buildings and parked cars.

Portland Regency Hotel & Spa

Downtown Portland

10/10 Excellent

This property is beautiful. It sits in the historic area of the old port. It is very close to the waterfront, restaurants, shops and historic areas. The mattress and sheets were superb. While in the old port, we took a trolley tour which took us out to Portland headlight and then gave us a tour of of the old port. You can catch fairies from about two or three minutes walk away, we would strongly recommend this hotel.

Debra

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

Mark

A fire pit surrounded by wicker chairs in a garden setting.

Portland Harbor Hotel

Downtown Portland

10/10 Excellent

Christopher

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

elizabeth

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

Noah

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

Lawrence

A backyard with a fire pit, wooden chairs, and a house with a porch.

Inn By The Sea

Cape Elizabeth

10/10 Excellent

James

A spacious living room with a large dining table, comfortable seating, and large windows offering views of the city.

The Docent's Collection at 121 Middle Street

Downtown Portland

10/10 Excellent

Jeffrey

The exterior of a Courtyard by Marriott hotel with a glass entrance, outdoor seating area, and a stone facade.

Courtyard Portland Downtown/Waterfront

Downtown Portland

10/10 Excellent

Anonymous traveler

A waterfront marina with boats docked, buildings with multiple windows, and a red building with a visible restaurant.

Hilton Garden Inn Portland Downtown Waterfront

Downtown Portland

10/10 Excellent

Robert

Evalina Hotel

Downtown Portland

10/10 Excellent

Centrally located in the Old Port, with views of the harbor, this was a last minute — therefore pricey — excellent find for a fall weekend getaway. Stylish, elegant rehab of 19th century granite industrial building. Whimsical decor notes referring to 19th century owner Evalina Fox. Nicely appointed kitchenette — though if you came to Portland for the foodie scene, you might end up just using it for breakfast, as we did. Only sour note was the disco music (coming in via the ventilation...

Christopher

A modern bar area with a bar counter, seating, and a view of the cityscape.

Aloft by Marriott Portland Downtown Waterfront ME

Downtown Portland

10/10 Excellent

Andre

A swimming pool with lounge chairs and tables, indoor lighting, and a ceiling with ventilation.

Holiday Inn Portland-By the Bay by IHG

Downtown Portland

10/10 Excellent

Sherry

The Weldon Hotel

Downtown Portland

10/10 Excellent

Amazing place to stay in Portland. The location was great. The hotel is right next to Courtyard Marriott and Aloft hotels, but it feels so much more comfortable. The unit was twice as large as a typical Marriott room about 700 sq. ft which was wonderful. It is Walkable to the ferry boat, restaurants and shops. There is a full kitchen, dining area, living area, very large island with large windows to brighten the place and a set of washer and dryer in the unit. Extremely clean and it looked...

Rana

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

RII

Find out more about Great Diamond Island

Everything you need to know about Great Diamond Island vacation rentals

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

Great Diamond Island vacation 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 low season months. For more hustle and bustle, you may prefer to visit Great Diamond Island in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $68 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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 vacation 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 vacation.

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.

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Great Diamond Island Vacation Rentals

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Our top choices for Great Diamond Island vacation 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 vacation rentals that suit your style

Top Great Diamond Island Hotel Reviews

Embassy Suites by Hilton Portland Maine

10/10 Excellent

Find out more about Great Diamond Island

Everything you need to know about Great Diamond Island vacation rentals

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

How to find incredible deals on Great Diamond Island rentals

Explore a world of travel with Expedia