A calm sea with a sailboat and rocky coastline.

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Dates

November 2026

December 2026

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Our top choices for Great Diamond Island condo rentals

A kitchen with wooden cabinets, a stainless steel dishwasher, a coffee maker, and a potted plant.

1. Cozy Two Bedroom on Munjoy Hill

Munjoy Hill

￥31,643 total

includes taxes & fees

Nov 10 - Nov 11

A nighttime street view with a building featuring a storefront with a sign that reads 'Beauty Joy.'

2. Renovated Exchange St. Loft w/Free Parking

Downtown Portland

￥31,195 total

includes taxes & fees

Nov 8 - Nov 9

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

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

Willard Beach

Jason M.

￥69,739 total

includes taxes & fees

Nov 30 - Dec 1

A living room with a television, a wooden chest, a glass coffee table, a sofa, and a chair.

4. Walk to Old Port ♦ West End Condo ♦ Parking

West End

Britney G.

￥53,129 total

includes taxes & fees

Nov 8 - Nov 9

5. Lux by the water and dining

Downtown Portland

￥121,195 total

includes taxes & fees

Nov 9 - Nov 10

A beach with a sunset, a pier, and a building with 'erly' on it.

6. Sleeps 3 • 1BR • Old Orchard Beach • 4-Min Walk

Old Orchard Beach

Joseph R.

￥48,332 total

includes taxes & fees

Nov 8 - Nov 9

7. Sleeps 4 • 1BR • Old Orchard Beach • 4-Min Walk

Old Orchard Beach

Jared C.

￥48,752 total

includes taxes & fees

Nov 7 - Nov 8

A pier with buildings on stilts, a sandy beach, and a clear sky.

8. Adorable, two-bedroom, one-bathroom condo, two short blocks from the beach!

Old Orchard Beach

Alana J.

￥52,015 total

includes taxes & fees

Nov 9 - Nov 10

A pier with a building on stilts over the beach.

9. Cozy 2-bedroom, 1-bathroom condo, two short blocks from the beach!

Old Orchard Beach

Katherine D.

￥52,015 total

includes taxes & fees

Nov 9 - Nov 10

A wooden boardwalk leading to a beach with a clear view of the ocean.

10. Ocean View Condo 3 by Everrow

Old Orchard Beach

Dawn T.

￥62,924 total

includes taxes & fees

Nov 10 - Nov 11

A compact kitchen with wooden cabinets, a stainless steel sink, and a white refrigerator.

11. Sleeps 3 • 1BR • OOB • 350 Yds to Beach

Old Orchard Beach

Phenix p.

￥42,412 total

includes taxes & fees

Nov 22 - Nov 23

A beach at night with a view of the ocean and a city skyline in the distance.

12. Direct ocean views from extra large balcony! Over 1200 square feet!

Old Orchard Beach

Kara C.

￥71,584 total

includes taxes & fees

Nov 7 - Nov 8

A balcony with a view of the beach, a white building in the background, and a wicker sofa with floral cushions.

13. Old Orchard Beach, Spacious, beachfront, 2 bedroom condo

Old Orchard Beach

"We absolutely loved our stay in Old Orchard. The beach was 10x nicer than we expected. Waking up for sunrise was a treat. The condo is spacious and loved having the windows open for the ocean breeze. We were able to grill lobster. Beds upstairs were super comfy. Better sleeping on the couch than the couch bed as the couch bed is terrible at best (there’s plenty of room on the couch). Kitchen is very sparse. Pick up all essentials in town (coffee, plastic wrap/foil, paper towels, paper cups,...

Ally M.

￥93,550 total

includes taxes & fees

Nov 9 - Nov 10

View all properties

Learn more about Great Diamond Island

Check out Sand Beach and East End Beach—just a couple of the sights around Great Diamond Island.

See all hotels in Great Diamond Island

Top reviews in Great Diamond Island

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

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 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

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

Daniel

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

Embassy Suites by Hilton Portland Maine

Portland

10/10 Excellent

Michael

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 fire pit surrounded by wicker chairs in a garden setting.

Portland Harbor Hotel

Downtown Portland

10/10 Excellent

Christopher

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

A balcony with wooden flooring, striped cushioned chairs, and a glass railing overlooking a cityscape at night.

Hyatt Place Portland Downtown - Old Port Square

Downtown Portland

10/10 Excellent

Douglas

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 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

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

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

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

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

The Press Hotel, Marriott Autograph Collection

Downtown Portland

10/10 Excellent

RII

A multi-story hotel with a prominent entrance, large windows, and a well-lit facade.

Hampton Inn Portland Downtown - Waterfront

Downtown Portland

10/10 Excellent

Courtney

Frequently Asked Questions

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Search Condos in Great Diamond Island

Change your mind

Treat yourself

Be picky

Find vacation rentals that suit your style

Check prices for these dates

Our top choices for Great Diamond Island condo rentals

1. Cozy Two Bedroom on Munjoy Hill

2. Renovated Exchange St. Loft w/Free Parking

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

4. Walk to Old Port ♦ West End Condo ♦ Parking

5. Lux by the water and dining

6. Sleeps 3 • 1BR • Old Orchard Beach • 4-Min Walk

7. Sleeps 4 • 1BR • Old Orchard Beach • 4-Min Walk

8. Adorable, two-bedroom, one-bathroom condo, two short blocks from the beach!

9. Cozy 2-bedroom, 1-bathroom condo, two short blocks from the beach!

10. Ocean View Condo 3 by Everrow

11. Sleeps 3 • 1BR • OOB • 350 Yds to Beach

12. Direct ocean views from extra large balcony! Over 1200 square feet!

13. Old Orchard Beach, Spacious, beachfront, 2 bedroom condo

Learn more about Great Diamond Island

Top reviews in Great Diamond Island

Inn On Peaks Island

10/10 Excellent

Frequently Asked Questions

Why book your condo in Great Diamond Island with Expedia?

How can I find cheap condos in Great Diamond Island?

Explore a world of travel with Expedia