Great Diamond Island Vacation Homes

A calm sea with a sailboat and rocky coastline.

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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.

HK$4,743 total

includes taxes & fees

14 Oct - 15 Oct

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

2. 1200 sq ft ♦ West End Townhouse ♦ Perfect Location

West End

Susan d.

HK$3,049 total

includes taxes & fees

29 Oct - 30 Oct

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.

3. 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.

HK$3,747 total

includes taxes & fees

29 Oct - 30 Oct

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

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

East Deering

Sally O.

HK$8,721 total

includes taxes & fees

5 Oct - 6 Oct

A two-story house with a balcony, a covered patio, and a fenced yard.

5. The Globe House on Munjoy Hill - Walk to Breweries

Munjoy Hill

Richard D.

HK$5,192 total

includes taxes & fees

6 Oct - 7 Oct

A restaurant window with 'OYSTER CO. EVENTIDE' signage, indicating a raw bar, chowders, and cocktails.

6. Modern & Sunny House Steps from the Promenade.

Munjoy Hill

stacey p.

HK$3,887 total

includes taxes & fees

5 Oct - 6 Oct

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

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

Munjoy Hill

Matt H.

HK$7,134 total

includes taxes & fees

28 Oct - 29 Oct

A snow-covered landscape with a house and a tree.

8. Serenity between the lakes and seashore

Westbrook

Joanne N.

A spacious living area with a blue sofa, a coffee table, and a kitchen in the background.

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

North Deering

Peter H.

HK$6,864 total

includes taxes & fees

18 Oct - 19 Oct

An outdoor seating area with tables and benches in front of a building with a sign reading "BRAKES & SHOCKS Specialty Bakery".

10. Spacious Portland Home + Parking

Parkside

Ellen M.

HK$5,569 total

includes taxes & fees

5 Oct - 6 Oct

A window with a view of a snowy landscape and bare trees.

11. Tranquility between the Lakes & Sea

Westbrook

HK$2,552 total

includes taxes & fees

5 Oct - 6 Oct

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

12. The 87th Townhome - Local Landmark

West End

Amy B.

HK$4,609 total

includes taxes & fees

3 Nov - 4 Nov

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

13. Mid Coast Getaway w/ water views

West Point

Rebecca

HK$1,683 total

includes taxes & fees

5 Oct - 6 Oct

A modern living room with a teal sofa, two glasses of white wine, a tray of food, and a decorative candle on a wooden table.

14. Sleeps 16+ | W/D | Parking | 15 mins to Old Port

Westbrook

damean s.

HK$7,416 total

includes taxes & fees

6 Oct - 7 Oct

A compact kitchen with a dishwasher, microwave, and coffee maker on the countertop.

15. Quiet Spot in lovely Freeport neighborhood

Freeport

HK$2,981 total

includes taxes & fees

16 Oct - 17 Oct

A living room with a fireplace, leather sofa, and a chandelier.

16. Charming Historic Estate | In-town location

West End

shelley w.

HK$20,726 total

includes taxes & fees

1 Nov - 2 Nov

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

17. Classic New England Waterfront House Big Lawn Beautiful Sunrise

Harpswell

Ashma B.

HK$13,951 total

includes taxes & fees

3 Nov - 4 Nov

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

18. Luxe 5 Bed/ 3 Bath with Game Room & AC

Yarmouth

Michelle T.

A wooden deck with outdoor seating and string lights.

19. Full sized home

Harpswell

Angela M.

HK$2,895 total

includes taxes & fees

5 Oct - 6 Oct

A spacious room with a wooden floor, a dining area with chairs and a table, a sofa, a TV, and a balcony with a view of the sea.

20. 2 bedroom w/ expansive water views

West Point

Gregory M.

HK$1,889 total

includes taxes & fees

1 Nov - 2 Nov

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Top Great Diamond Island Hotel Reviews

Clarion Hotel Portland Airport ME

10/10 Excellent

"Close to the bus/train station."

Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

10/10 Excellent

"The pillows were too fluffy though so I woke up with headaches unless I used a flatter pillow. I’m also allergic to maple and that’s the syrup they have so I had to bring my own. Unfortunately the laundry hours are 9-7pm, which to me is not enough hours of operation since getting to the hotel in the evening has us missing the evening time and since check out time is 11am, that kind of cuts it close for washing, drying, and packing. An 8-8 pm system would be better. Other than that that, they replenished towels, soap, made the beds when asked, and the staff was friendly! Very clean, friendly, and I can’t rave enough about how comfortable the beds were!!!"

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

10/10 Excellent

"Location was good; close to downtown, but not walkable. Room was clean; public areas did not feel as clean. Breakfast options were fine but not extensive, and the same both days we were there. Had to pay for parking, which was a surprise."

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