Great Diamond Island Holiday House Rentals from AU$294: Search Holiday Homes

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Our top choices for Great Diamond Island holiday homes

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

1. Willard Square Family Home

Willard Beach

David W.

includes taxes & fees

12 Nov - 13 Nov

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.

2. Chic 3-bedroom house in Munjoy Hill with off-street parking.

Munjoy Hill

"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...

Maris P.

includes taxes & fees

11 Nov - 12 Nov

A staircase with white railings and wooden steps leading to a dining area with a table and chairs.

3. 1200 sq ft ♦ West End Townhouse ♦ Perfect Location

West End

Susan d.

includes taxes & fees

9 Nov - 10 Nov

A modern kitchen with a central island, a dining area with a sofa and chairs, and a living room with a colorful rug and plants.

4. Modern & Sunny East End House.

Munjoy Hill

stacey p.

includes taxes & fees

12 Nov - 13 Nov

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

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

East Deering

Mike G.

includes taxes & fees

8 Nov - 9 Nov

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

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

Munjoy Hill

Matt H.

includes taxes & fees

9 Nov - 10 Nov

A residential backyard with a fire pit, outdoor seating, and a house with a dark exterior.

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

North Deering

Patrick J.

includes taxes & fees

22 Nov - 23 Nov

A wooden covered porch with a green door, potted plants, and a red watering can.

8. Charming West End Victorian

Parkside

includes taxes & fees

1 Dec - 2 Dec

A red building with a front door, a bay window, and a brick pathway.

9. Spacious Portland Home + Parking

Parkside

Ellen M.

includes taxes & fees

12 Nov - 13 Nov

A two-story brick building with a front porch, a black door, and a window with a white frame.

10. The 87th Townhome by Everrow

West End

Amy B.

includes taxes & fees

9 Nov - 10 Nov

11. Steps to Old Port, balcony, private outdoor space

Downtown Portland

includes taxes & fees

12 Nov - 13 Nov

A living room with a sofa, armchair, wooden coffee table, and a potted plant.

12. Fully Updated Airy Historic Home in South Freeport

Freeport

boodu

includes taxes & fees

6 Nov - 7 Nov

A two-story house with a stone staircase leading to a front door, surrounded by a garden with potted plants and a seating area with chairs.

13. Charming Historic Estate | In-town location

West End

shelley w.

includes taxes & fees

8 Nov - 9 Nov

A grassy area with a picnic table and chairs, a body of water, and two trees in the background.

14. Orchid Harbor, Bailey Island 3BR

Harpswell

Jane D.

includes taxes & fees

10 Nov - 11 Nov

A dining area with a wooden table and chairs, a red sofa, and a small round table with a decorative plate.

15. Quiet Spot in lovely Freeport neighborhood

Freeport

includes taxes & fees

6 Nov - 7 Nov

A spacious living room with a sofa, ottoman, and coffee table, a dining area with chairs, and a kitchen with cabinets and appliances.

16. Newly Renovated Luxury House with Game Room

Yarmouth

Michelle T.

includes taxes & fees

9 Nov - 10 Nov

A sunroom with a glass ceiling, outdoor seating, a hot tub, and a stone wall.

17. Coastal Retreat - Sauna, Hot Tub & Swim Spa - Near Beaches and Downtown Portland

Scarborough

Stuart R.

includes taxes & fees

9 Nov - 10 Nov

A cozy living room with a wooden ceiling, a sofa, a table, and a sliding glass door leading to a balcony.

18. Mid Coast Getaway w/ water views

West Point

Rebecca

includes taxes & fees

8 Nov - 9 Nov

A lush garden with a hammock, a variety of flowers, and a lake in the background.

19. Classic New England Waterfront House Big Lawn Beautiful Sunrise

Harpswell

Ashma B.

includes taxes & fees

30 Nov - 1 Dec

A covered porch with a view of a lake and trees.

20. Mere Point Sunrise Views at Eastern Shore!

Brunswick

Michelle S.

includes taxes & fees

16 Nov - 17 Nov

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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

A calm sea with a sailboat and rocky coastline.

Top reviews in Great Diamond Island

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