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$3,023 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$3,755 total

includes taxes & fees

29 Oct - 30 Oct

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

4. Modern & Sunny House Steps from the Promenade.

Munjoy Hill

stacey p.

HK$3,960 total

includes taxes & fees

1 Nov - 2 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

Sally O.

HK$9,622 total

includes taxes & fees

2 Nov - 3 Nov

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

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

Munjoy Hill

Richard D.

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$7,133 total

includes taxes & fees

28 Oct - 29 Oct

A modern kitchen with white cabinetry, a black countertop, and stainless steel appliances.

8. "Good Vibes" 4 Wonderful Seasons @ Portland Home!

North Deering

Shannon L.

A modern kitchen with dark cabinetry, stainless steel appliances, and a large island.

9. Gorgeous 3-bedroom house in charming Portland

North Deering

Bridget M.

HK$5,894 total

includes taxes & fees

31 Oct - 1 Nov

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

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

North Deering

Peter H.

HK$6,857 total

includes taxes & fees

18 Oct - 19 Oct

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

11. The 87th Townhome - Local Landmark

West End

Amy B.

HK$4,646 total

includes taxes & fees

3 Nov - 4 Nov

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

12. Spacious Portland Home + Parking

Parkside

Ellen M.

HK$5,568 total

includes taxes & fees

7 Oct - 8 Oct

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

13. Tranquility between the Lakes & Sea

Westbrook

HK$2,644 total

includes taxes & fees

11 Oct - 12 Oct

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

14. Charming Historic Estate | In-town location

West End

shelley w.

HK$20,724 total

includes taxes & fees

1 Nov - 2 Nov

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

16. Mid Coast Getaway w/ water views

West Point

Rebecca

HK$1,683 total

includes taxes & fees

2 Nov - 3 Nov

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.

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

Westbrook

damean s.

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

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

Scarborough

Stuart R.

HK$6,522 total

includes taxes & fees

13 Oct - 14 Oct

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.

HK$14,070 total

includes taxes & fees

4 Nov - 5 Nov

A spacious living room with large windows, a sofa, a chair, and a small table.

20. 1 Mi to Maine Street! MCM-Style Home in Brunswick

Brunswick

Kendra G.

HK$2,575 total

includes taxes & fees

20 Oct - 21 Oct

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Top Great Diamond Island Hotel Reviews

DoubleTree by Hilton Hotel Portland

10/10 Excellent

"I liked that it had an indoor pool, bar and restaurant."

Embassy Suites by Hilton Portland Maine

8/10 Good

"Great hotel with one exception. The pillows were awful. If I'm paying over $300 a night for a hotel room, I want a pillow that's better than the $2 special at Walmart. The pillows felt like they were cubes foam, and there was no heft to them at all. Your head was essentially laying on the bed because the foam separated."

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