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

15 Oct - 16 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

20 Oct - 21 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$3,806 total

includes taxes & fees

29 Oct - 30 Oct

A modern kitchen with a central island, wooden shelves, and a dining area with a colorful rug.

4. Modern & Sunny House Steps from the Promenade.

Munjoy Hill

stacey p.

HK$4,012 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$8,721 total

includes taxes & fees

12 Oct - 13 Oct

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$7,134 total

includes taxes & fees

28 Oct - 29 Oct

A living room with a sofa, a coffee table, and a vase on a windowsill.

7. Rare West End Home • Walk to Old Port, Harbor View

West End

Nikki W.

HK$3,980 total

includes taxes & fees

13 Oct - 14 Oct

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

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

North Deering

Peter H.

HK$6,817 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".

9. Spacious Portland Home + Parking

Parkside

Ellen M.

HK$5,569 total

includes taxes & fees

12 Oct - 13 Oct

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

10. The 87th Townhome - Local Landmark

West End

Amy B.

HK$4,591 total

includes taxes & fees

2 Nov - 3 Nov

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

11. Tranquility between the Lakes & Sea

Westbrook

HK$2,754 total

includes taxes & fees

21 Oct - 22 Oct

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

12. Orchid Harbor, Bailey Island 3BR

Harpswell

Jane D.

HK$3,494 total

includes taxes & fees

27 Oct - 28 Oct

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

13. Charming Historic Estate | In-town location

West End

shelley w.

HK$20,726 total

includes taxes & fees

1 Nov - 2 Nov

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

14. Quiet Spot in lovely Freeport neighborhood

Freeport

HK$2,955 total

includes taxes & fees

11 Oct - 12 Oct

A modern interior with a glass door leading to an outdoor deck with a sofa and a hanging light fixture.

15. Whole Home | Sleeps 16 | Roof Deck|5 mins Downtown

Oakdale

"Great, renovated set of three units. The location was convenient along with the three parking spots. Window and mini split AC units worked well. The loft space and roof deck on the third floor was particularly nice for hanging out. The ice makers didn’t work and a couple other maintenance issues, but the owner said they would be fixing them. All in, a great space for our family of 11 to explore Portland. "

Andy W.

HK$13,796 total

includes taxes & fees

15 Oct - 16 Oct

A stone fireplace with a TV mounted above it, a wooden mantel, and a hanging light fixture.

16. The Outlet Studio, Rustic Comfort w Fireplace

Freeport

Joanne H.

HK$2,138 total

includes taxes & fees

11 Oct - 12 Oct

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

17. Mid Coast Getaway w/ water views

West Point

Rebecca

HK$1,683 total

includes taxes & fees

8 Nov - 9 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 sunroom with a glass ceiling, outdoor seating, a hot tub, and a stone wall.

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

Scarborough

Stuart R.

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

20. Classic New England Waterfront House Big Lawn Beautiful Sunrise

Harpswell

Ashma B.

HK$14,071 total

includes taxes & fees

4 Nov - 5 Nov

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Top Great Diamond Island Hotel Reviews

Hampton Inn Portland Downtown - Waterfront

10/10 Excellent

"The breakfast was good."

Spark by Hilton Portland Airport Maine Mall

8/10 Good

"It was mostly good. Still carrying the Hilton name, I expected it to be nicer. But, on the other hand, I understand that they're taking an old hotel and giving it the Spark refresh. Airport shuttle was nice to have, though no grab-and-go breakfast options were available, despite the breakfast being grab-n-go in the first place. Nice people."

DoubleTree by Hilton Hotel Portland

10/10 Excellent

"I’m very happy with this hotel. The airport shuttle works perfectly. The front staff was very good. I can’t say enough nice things about the bar/breakfast employees, some of the nicest people I’ve ever met. The room was clean and spacious, the mattress and bedding were very good. Thank you Doubletree!"

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