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$5,041 total

includes taxes & fees

16 Nov - 17 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.

HK$3,121 total

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.

HK$2,899 total

includes taxes & fees

9 Nov - 10 Nov

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

Mike G.

HK$8,305 total

includes taxes & fees

5 Nov - 6 Nov

A staircase with a wooden handrail, a compass wall decoration, and a potted plant.

5. Modern & Sunny East End House.

Munjoy Hill

stacey p.

HK$4,399 total

includes taxes & fees

30 Nov - 1 Dec

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.

HK$6,781 total

includes taxes & fees

4 Nov - 5 Nov

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

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

North Deering

Patrick J.

HK$6,037 total

includes taxes & fees

22 Nov - 23 Nov

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

8. Spacious Portland Home + Parking

Parkside

Ellen M.

HK$4,780 total

includes taxes & fees

4 Nov - 5 Nov

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

9. Charming West End Victorian

Parkside

HK$5,943 total

includes taxes & fees

1 Dec - 2 Dec

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.

HK$4,542 total

includes taxes & fees

1 Dec - 2 Dec

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

11. Tranquility between the Lakes & Sea

Westbrook

Bernie G.

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

Downtown Portland

HK$9,500 total

includes taxes & fees

8 Nov - 9 Nov

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

13. Fully Updated Airy Historic Home in South Freeport

Freeport

boodu

HK$3,617 total

includes taxes & fees

6 Nov - 7 Nov

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

14. Mid Coast Getaway w/ water views

West Point

Rebecca

HK$1,319 total

includes taxes & fees

4 Nov - 5 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.

15. Charming Historic Estate | In-town location

West End

shelley w.

HK$19,684 total

includes taxes & fees

4 Nov - 5 Nov

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

16. Orchid Harbor, Bailey Island 3BR

Harpswell

Jane D.

HK$2,807 total

includes taxes & fees

10 Nov - 11 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.

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

18. Newly Renovated Luxury House with Game Room

Yarmouth

Michelle T.

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

19. Quiet Spot in lovely Freeport neighborhood

Freeport

HK$3,012 total

includes taxes & fees

4 Nov - 5 Nov

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

20. Mere Point Sunrise Views at Eastern Shore!

Brunswick

Michelle S.

HK$2,861 total

includes taxes & fees

16 Nov - 17 Nov

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Top Great Diamond Island Hotel Reviews

Hampton Inn Portland Downtown - Waterfront

10/10 Excellent

"Our room was ready even though we got there earlier than check in. The room was clean. The staff were friendly. Breakfast was good."

Hilton Garden Inn Portland Downtown Waterfront

10/10 Excellent

"We enjoyed the weekend spending time together celebrating our 4 year wedding anniversary. Everything was perfect. We wanted the hot tub but it was unavailable at the time we stayed. Maybe next time. But we didn’t let that stop us from enjoying the beautiful weather and walking around the shops. Enjoying good food and drinks. Coming back to Portland again"

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