Great Diamond Island Vacation Rentals from $147: Search Short-Term Rentals

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Our top choices for Great Diamond Island vacation rentals

A dining table with chairs, a potted plant, and decorative items.

1. Willard Beach–Apartment Near Portland & Parks

Willard Beach

Linda

$288 nightly

Oct 25 - Oct 26

Total with taxes and fees

A street lined with buildings, one with a red door and a sign that reads "MINATO".

2. Adorable Portland getaway on the Eastern Promenade

Munjoy Hill

Kiernan

$264 nightly

Oct 20 - Oct 21

Total with taxes and fees

A kitchen with a wooden countertop, a black kettle, a vase with flowers, and a small wire basket.

3. Charming Studio Retreat with Queen bed, WiFi, and AC in welcoming Portland

Munjoy Hill

Aimee S.

$211 nightly

Nov 1 - Nov 2

Total with taxes and fees

A bedroom with a bed, a nightstand, a lamp, a door, and a staircase.

4. Great suburban location close to town!

Deering Center

Peter H.

$95 nightly

Oct 25 - Oct 26

Total with taxes and fees

A multi-story building with a stone facade, large windows, and a corner entrance.

5. Evalina Hotel

Downtown Portland

Rick

$426 nightly

Nov 9 - Nov 10

Total with taxes and fees

A bedroom with a wooden bed, a nightstand, a bench, a chair, and a ceiling with a light fixture.

6. Studio Apartment near downtown Walkable!

West Bayside

Lucy T.

$149 nightly

Nov 1 - Nov 2

Total with taxes and fees

A modern kitchen with a central island, bar stools, a dining table, and a built-in oven.

7. The Weldon Hotel

Downtown Portland

Victoria

$292 nightly

Nov 2 - Nov 3

Total with taxes and fees

A modern house with a wooden exterior, a small garden, and a visible window.

8. Spacious and Contemporary Condo in the Heart of Portland - Close to Beach

East Bayside

Mallory D.

$432 nightly

Oct 18 - Oct 19

Total with taxes and fees

A modern kitchen with a wooden countertop, a glass coffee table, and a built-in shelf with kitchenware.

9. Sunny Spot with Private Parking.

Knightville

Irish D.

$298 nightly

Oct 18 - Oct 19

Total with taxes and fees

A living room with a sofa, armchair, and glass coffee table. There are two lamps on side tables and a window with curtains.

10. Portland 1-bedroom with enclosed porch & parking

Deering Center

Cricket C.

$109 nightly

Oct 13 - Oct 14

Total with taxes and fees

A beach with a wooden chair and a small building in the background.

11. Arlie`s Digs! - One Block To Willard Beach!

Willard Beach

Melissa M.

$431 nightly

Nov 8 - Nov 9

Total with taxes and fees

A modern kitchen with a dining area, featuring a round table, chairs, and a hanging light fixture.

12. Elegant condo - walk to Portland's best restaurants & Old Port

East Bayside

Nancy S.

$468 nightly

Oct 13 - Oct 14

Total with taxes and fees

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

13. Beautiful 1st Floor Apartment & Amazing Shower

Parkside

Jocelyn R.

$168 nightly

Nov 9 - Nov 10

Total with taxes and fees

14. Ocean View East End Studio in a Historic Victorian

Portland

Ryan S.

$426 nightly

Oct 13 - Oct 14

Total with taxes and fees

A black console table with a mirror above it, a lamp, and a potted plant beside it.

15. Peaceful & minutes from the Old Port with private parking

Knightville

Kelly S.

$306 nightly

Nov 1 - Nov 2

Total with taxes and fees

A coastal view with a house, a tree, and a beach.

16. Willard By the Sea - 30 ft to the beach- 2nd floor

Willard

"Fantastic beach location and comfortable unit equipped with air conditioning (essential during the heat wave that occurred during our stay). Clean rooms, good size and full kitchen; comfortable furnishings.Only caution is that this is a beach-side location and appears to have a bit of a price premium for that reason. It’s justified but only if you’re planning to make good use of the beach."

Gerald B.

$557 nightly

Nov 9 - Nov 10

Total with taxes and fees

A house with a wooden staircase leading to a door marked with the number 50.

17. 1200 Sq Ft ♦ West End Gem ♦ Perfect Location

West End

Gary

$247 nightly

Nov 3 - Nov 4

Total with taxes and fees

A room with a wooden floor, a round table, two chairs, a sofa, and a patterned rug.

18. NEW 1 BDR-Heart of Munjoy Hill

Munjoy Hill

Susan

$385 nightly

Oct 20 - Oct 21

Total with taxes and fees

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

19. 1200 sq ft ♦ West End Townhouse ♦ Perfect Location

West End

Susan d.

$356 nightly

Oct 20 - Oct 21

Total with taxes and fees

20. Glorious getaway on Portland's Eastern Promenade.

Munjoy Hill

William

$377 nightly

Oct 14 - Oct 15

Total with taxes and fees

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Top Great Diamond Island Hotel Reviews

Clarion Pointe South Portland

8/10 Good

"It was a clean room with comfortable beds. Does have pool and weight room. Average. Staff acted like she couldn't be bothered"

Fireside Inn & Suites Portland

8/10 Good

"This hotel is a modest place just outside of Portland. The price/ value is good. But it’s a bit dated. The fitness room has only a few pieces of equipment and for a hotel this big it needs more. The hot tub was lovely but very small. The indoor pool did not open until 9:00am which was unfortunate since every piece of gym equipment was being used so we could not access the pool before we had to leave. The hotel room was large but in the rear of the building facing highway. There are a few complimentary light breakfast items available. Overall it worked out for our needs."

Holiday Inn Portland-By the Bay by IHG

10/10 Excellent

"We were in Portland for three (3) days on the tail end of our 2-week east coast trip. While the hotel is showing some signs of age, it did not disappoint and fully met our needs. The breakfast was great, especially the cook to order omelets. The hotel is not in the Old Port area but is still a comfortable 15-minute walk to get to the harbor area for dinner, bay tours and site seeing. The only negative was our last day and being awakened with two (2) room attendant staffers arguing in the hall. It lasted about 5 minutes until we came out into the hallway and glared at both of the participants. We will definitely stay here again when we come back either in 27 or 28."

Find out more about Great Diamond Island

Everything you need to know about Great Diamond Island vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Great Diamond Island vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Great Diamond Island vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Great Diamond Island vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Great Diamond Island. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Great Diamond Island in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $147 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Great Diamond Island rentals

At Expedia, we put the best Great Diamond Island vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Great Diamond Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Great Diamond Island vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Great Diamond Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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Check prices for these dates

Our top choices for Great Diamond Island vacation rentals

1. Willard Beach–Apartment Near Portland & Parks

2. Adorable Portland getaway on the Eastern Promenade

3. Charming Studio Retreat with Queen bed, WiFi, and AC in welcoming Portland

4. Great suburban location close to town!

5. Evalina Hotel

6. Studio Apartment near downtown Walkable!

7. The Weldon Hotel

8. Spacious and Contemporary Condo in the Heart of Portland - Close to Beach

9. Sunny Spot with Private Parking.

10. Portland 1-bedroom with enclosed porch & parking

11. Arlie`s Digs! - One Block To Willard Beach!

12. Elegant condo - walk to Portland's best restaurants & Old Port

13. Beautiful 1st Floor Apartment & Amazing Shower

14. Ocean View East End Studio in a Historic Victorian

15. Peaceful & minutes from the Old Port with private parking

16. Willard By the Sea - 30 ft to the beach- 2nd floor

17. 1200 Sq Ft ♦ West End Gem ♦ Perfect Location

18. NEW 1 BDR-Heart of Munjoy Hill

19. 1200 sq ft ♦ West End Townhouse ♦ Perfect Location

20. Glorious getaway on Portland's Eastern Promenade.

Find vacation rentals that suit your style

Top Great Diamond Island Hotel Reviews

Clarion Pointe South Portland

Find out more about Great Diamond Island

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