A calm sea with a sailboat and rocky coastline.

Great Diamond Island Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

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–Apartment Near Portland & Parks
Willard Beach
10.0 out of 10, Exceptional, (8 reviews)
"Excellent in every way."
United States
Robert B.
$304 nightly
The price is $332
Oct 27 - Oct 28
Total with taxes and fees
Willard Beach–Apartment Near Portland & Parks
A bedroom with a bed, a nightstand, a lamp, a door, and a staircase.

2. Great suburban location close to town!

Great suburban location close to town!
Deering Center
10.0 out of 10, Exceptional, (1 review)
"Small but cozy space, well kept, good value for the price and has all the amenities you could expect. Would be happy to stay here again."
United States
Peter H.
$95 nightly
The price is $97
Oct 25 - Oct 26
Total with taxes and fees
Great suburban location close to town!
A living room with a sofa, armchair, and glass coffee table. There are two lamps on side tables and a window with curtains.

3. Portland 1-bedroom with enclosed porch & parking

Portland 1-bedroom with enclosed porch & parking
Deering Center
8.2 out of 10, Very good, (15 reviews)
"As expected."
United States
Lance
$109 nightly
The price is $111
Oct 5 - Oct 6
Total with taxes and fees
Portland 1-bedroom with enclosed porch & parking
A street lined with buildings, one with a red door and a sign that reads "MINATO".

4. Adorable Portland getaway on the Eastern Promenade

Adorable Portland getaway on the Eastern Promenade
Munjoy Hill
9.6 out of 10, Exceptional, (149 reviews)
"Owner was so accommodating!"
United States
Kiernan
$262 nightly
The price is $286
Oct 20 - Oct 21
Total with taxes and fees
Adorable Portland getaway on the Eastern Promenade
A kitchen with a wooden countertop, a black kettle, a vase with flowers, and a small wire basket.

5. Charming Studio apartment with WiFi, AC in welcoming Portland

Charming Studio apartment with WiFi, AC in welcoming Portland
Munjoy Hill
9.6 out of 10, Exceptional, (29 reviews)
"Loved this spot and would stay again. Had everything you needed and a great location. Cute little attic spot but nice and cool."
United States
Emily N.
$209 nightly
The price is $228
Oct 23 - Oct 24
Total with taxes and fees
Charming Studio apartment with WiFi, AC in welcoming Portland
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!

Studio Apartment near downtown Walkable!
West Bayside
8.4 out of 10, Very good, (21 reviews)
"I will admit the location and surrounding areas are a bit sketchy, but, once inside, we felt super secure. There are multiple doors and gates with locks to ensure safety. Place was clean and had everything we needed for a quick stay."
United States
Krysta
$149 nightly
The price is $151
Nov 1 - Nov 2
Total with taxes and fees
Studio Apartment near downtown Walkable!
A modern house with a wooden exterior, a small garden, and a visible window.

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

Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
East Bayside
8.8 out of 10, Excellent, (40 reviews)
"Overall a pleasing stay."
United States
Mallory D.
$429 nightly
The price is $467
Oct 4 - Oct 5
Total with taxes and fees
Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
A modern kitchen with a dining area, featuring a round table, chairs, and a hanging light fixture.

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

Elegant condo - walk to Portland's best restaurants & Old Port
East Bayside
9.2 out of 10, Wonderful, (85 reviews)
"It was nice if you like being right in town. There is no view and it's a bit noisy."
United States
Nancy S.
$465 nightly
The price is $507
Oct 8 - Oct 9
Total with taxes and fees
Elegant condo - walk to Portland's best restaurants & Old Port
A staircase with white railings and wooden steps leading to a dining area with a table and chairs.

9. 1200 sq ft ♦ West End Townhouse ♦ Perfect Location

1200 sq ft ♦ West End Townhouse ♦ Perfect Location
West End
8.4 out of 10, Very good, (61 reviews)
"Nice place, good location and very responsive host. I would definitely stay again when in Portland."
United States
Susan d.
$356 nightly
The price is $388
Oct 29 - Oct 30
Total with taxes and fees
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
A living room with a sofa, armchairs, a coffee table, and a potted plant.

10. Beautiful 1st Floor Apartment & Amazing Shower

Beautiful 1st Floor Apartment & Amazing Shower
Parkside
9.0 out of 10, Wonderful, (32 reviews)
"This was a clean and good location for our stay. "
United States
Jocelyn R.
$190 nightly
The price is $207
Oct 7 - Oct 8
Total with taxes and fees
Beautiful 1st Floor Apartment & Amazing Shower
A modern kitchen with a wooden countertop, a glass coffee table, and a built-in shelf with kitchenware.

11. Sunny Spot with Private Parking.

Sunny Spot with Private Parking.
Knightville
10.0 out of 10, Exceptional, (34 reviews)
"This is a perfect location. 6 minutes from downtown Portland. Secure, Clean and Jen was a Perfect and attentive host. It is a hidden Gem!"
United States
Irish D.
$296 nightly
The price is $323
Oct 8 - Oct 9
Total with taxes and fees
Sunny Spot with Private Parking.
Exterior

12. Ocean View East End Studio in a Historic Victorian

Ocean View East End Studio in a Historic Victorian
Portland
10.0 out of 10, Exceptional, (113 reviews)
"Fantastic host, fantastic place, fantastic location. 30 second walk out to a massive green lawned park overlooking the water. Easy stroll downtown. Dan was a very friendly, welcoming, and accommodating host. We had a great stay and would return again."
United States
Ryan S.
$423 nightly
The price is $461
Oct 13 - Oct 14
Total with taxes and fees
Ocean View East End Studio in a Historic Victorian
A living room with a television, a wooden chest, a glass coffee table, a sofa, and a chair.

13. Walk to Old Port ♦ West End Condo ♦ Parking

Walk to Old Port ♦ West End Condo ♦ Parking
West End
9.6 out of 10, Exceptional, (91 reviews)
"Was great for our few days in Portland! Having a designated parking space was great and the location was convenient for everything we wanted to do."
United States
Britney G.
$347 nightly
The price is $378
Oct 26 - Oct 27
Total with taxes and fees
Walk to Old Port ♦ West End Condo ♦ Parking
A room with a wooden floor, a round table, two chairs, a sofa, and a patterned rug.

14. NEW 1 BDR-Heart of Munjoy Hill

NEW 1 BDR-Heart of Munjoy Hill
Munjoy Hill
10.0 out of 10, Exceptional, (12 reviews)
"Lovely property - exceptionally clean and really well equipped with little touches that made it even better. Great location - up a bit of a hill but near Washington Ave and nice little coffee shops and restaurants. Great communication from the host and a very comfortable stay."
United Kingdom
Kate
$383 nightly
The price is $417
Oct 5 - Oct 6
Total with taxes and fees
NEW 1 BDR-Heart of Munjoy Hill
A beach with a wooden chair and a small building in the background.

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

Arlie`s Digs! - One Block To Willard Beach!
Willard Beach
10.0 out of 10, Exceptional, (70 reviews)
"Beautiful place, perfect location! "
United States
Melissa M.
$466 nightly
The price is $508
Oct 26 - Oct 27
Total with taxes and fees
Arlie`s Digs! - One Block To Willard Beach!
A kitchen with wooden cabinets, a stainless steel sink, and a potted plant.

16. Bright & Spacious Apartment with Amazing Shower

Bright & Spacious Apartment with Amazing Shower
Parkside
8.6 out of 10, Excellent, (27 reviews)
"Lovely apartment, in a pristine location. Very spacious and comfortable all around. Highly recommended this place for your next stay in Portland, Maine!"
United States
Gintare V.
$225 nightly
The price is $245
Nov 1 - Nov 2
Total with taxes and fees
Bright & Spacious Apartment with Amazing Shower
A black console table with a mirror above it, a lamp, and a potted plant beside it.

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

Peaceful & minutes from the Old Port with private parking
Knightville
9.8 out of 10, Exceptional, (13 reviews)
"Cute, convenient spot!"
United States
Kelly S.
$307 nightly
The price is $335
Nov 1 - Nov 2
Total with taxes and fees
Peaceful & minutes from the Old Port with private parking
A room with a ceiling fan, a framed plant artwork, a blue sofa, and a wooden table.

18. Charming 2-bedroom apartment with AC, WiFi in fabulous Portland

Charming 2-bedroom apartment with AC, WiFi in fabulous Portland
Munjoy Hill
8.4 out of 10, Very good, (9 reviews)
"This apartment was perfect for a stay in Portland!"
United States
Jennifer F.
$276 nightly
The price is $301
Nov 3 - Nov 4
Total with taxes and fees
Charming 2-bedroom apartment with AC, WiFi in fabulous Portland
A building named Willard Square with a storefront and a red vehicle parked outside.

19. Willard Square Family Home

Willard Square Family Home
Willard Beach
9.8 out of 10, Exceptional, (13 reviews)
"Thoroughly enjoyed this house! "
United States
David W.
$571 nightly
The price is $604
Oct 14 - Oct 15
Total with taxes and fees
Willard Square Family Home
A street lined with buildings, one with a red door and a sign that reads "MINATO".

20. Glorious getaway on Portland's Eastern Promenade.

Glorious getaway on Portland's Eastern Promenade.
Munjoy Hill
9.8 out of 10, Exceptional, (186 reviews)
"Wonderful experience with exceptional hosts!"
United States
Cynthia
$425 nightly
The price is $463
Oct 14 - Oct 15
Total with taxes and fees
Glorious getaway on Portland's Eastern Promenade.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Great Diamond Island Hotel Reviews

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 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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