Great Diamond Island, ME Vacation Homes from AED 788

A calm sea with a sailboat and rocky coastline.

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Our top choices for Great Diamond Island vacation homes

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

1. Willard Square Family Home

Willard Beach

David W.

AED 2,220 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.

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.

AED 1,762 total

includes taxes & fees

29 Oct - 30 Oct

A storefront with the sign "OYSTERS" and a "RAW BAR" sign above the entrance.

4. Modern & Sunny House Steps from the Promenade.

Munjoy Hill

stacey p.

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.

AED 4,082 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.

AED 3,339 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.

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.

AED 3,153 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.

AED 2,606 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.

AED 2,140 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

AED 1,210 total

includes taxes & fees

13 Oct - 14 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.

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

13. Charming Historic Estate | In-town location

West End

shelley w.

AED 9,701 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

AED 1,383 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

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.

AED 1,001 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

AED 788 total

includes taxes & fees

1 Nov - 2 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.

AED 4,001 total

includes taxes & fees

12 Oct - 13 Oct

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.

AED 2,678 total

includes taxes & fees

9 Nov - 10 Nov

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.

AED 6,530 total

includes taxes & fees

3 Nov - 4 Nov

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Top Great Diamond Island Hotel Reviews

Grand Beach Inn

8/10 Good

"Went there during May, but it rain and was a bit cold so couldn’t use the outdoor pool. But they are so many stuff to do near old orchard."

Inn at St John Portland In-Town

10/10 Excellent

"Nice clean hotel. Don’t believe those saying area is unsafe. No people were even out and about except for daily business. Parking is tight, you might be referred to a lot a very short walk away. Hotel is over 120 years old, they have maintained the decor of the period, and in some spots it needs some attention, but it would not detract from the stay. We had a room on the side and it was quiet and comfortable."

Holiday Inn Portland-By the Bay by IHG

8/10 Good

"Hotel was satisfactory. Room was clean although the bathroom needs to be repainted. Staff was accommodating. No real issues or concerns aside from the fact that its location is several blocks away from the seaport activities. Also the parking spaces underneath the hotel are not really designed for todays SUV's its kind of tight. I might consider it again but most likely would choose something a bit closer to the seaport due to its location."

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!"

Room 1

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Treat yourself

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Check prices for these dates

Our top choices for Great Diamond Island vacation homes

1. Willard Square Family Home

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

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

4. Modern & Sunny House Steps from the Promenade.

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

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

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

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

9. Spacious Portland Home + Parking

10. The 87th Townhome - Local Landmark

11. Tranquility between the Lakes & Sea

12. Orchid Harbor, Bailey Island 3BR

13. Charming Historic Estate | In-town location

14. Quiet Spot in lovely Freeport neighborhood

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

16. The Outlet Studio, Rustic Comfort w Fireplace

17. Mid Coast Getaway w/ water views

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

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

20. Classic New England Waterfront House Big Lawn Beautiful Sunrise

Find vacation rentals that suit your style

Top Great Diamond Island Hotel Reviews

Grand Beach Inn

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

Clarion Pointe South Portland

Spark by Hilton Portland Airport Maine Mall

Inn at St John Portland In-Town

Holiday Inn Portland-By the Bay by IHG

DoubleTree by Hilton Hotel Portland

Explore a world of travel with Expedia

Search Vacation Homes in Great Diamond Island

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Great Diamond Island vacation homes

1. Willard Square Family Home

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

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

4. Modern & Sunny House Steps from the Promenade.

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

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

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

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

9. Spacious Portland Home + Parking

10. The 87th Townhome - Local Landmark

11. Tranquility between the Lakes & Sea

12. Orchid Harbor, Bailey Island 3BR

13. Charming Historic Estate | In-town location

14. Quiet Spot in lovely Freeport neighborhood

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

16. The Outlet Studio, Rustic Comfort w Fireplace

17. Mid Coast Getaway w/ water views

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

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

20. Classic New England Waterfront House Big Lawn Beautiful Sunrise

Find vacation rentals that suit your style

Top Great Diamond Island Hotel Reviews

Grand Beach Inn

Explore a world of travel with Expedia