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 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

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, (9 reviews)
"Location and parking were perfect for our first visit to Portland"
United States
Linda
$286 nightly
The price is $312
Oct 19 - Oct 20
Total with taxes and fees
Willard Beach–Apartment Near Portland & Parks
A street lined with buildings, one with a red door and a sign that reads "MINATO".

2. Adorable Portland getaway on the Eastern Promenade

Adorable Portland getaway on the Eastern Promenade
Munjoy Hill
9.6 out of 10, Exceptional, (155 reviews)
"Owner was so accommodating!"
United States
Kiernan
$265 nightly
The price is $289
Oct 26 - Oct 27
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.

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

Charming Studio Retreat with Queen bed, WiFi, and AC in welcoming Portland
Munjoy Hill
9.4 out of 10, Exceptional, (32 reviews)
"Had a wonderful stay. Very clean and great location."
United States
Aimee S.
$211 nightly
The price is $230
Nov 1 - Nov 2
Total with taxes and fees
Charming Studio Retreat with Queen bed, WiFi, and AC in welcoming Portland
A modern kitchen with a central island, bar stools, a dining table, and a built-in oven.

4. The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (126 reviews)
"Really nice room and location"
United States
Victoria
$271 nightly
The price is $289
Nov 18 - Nov 19
Total with taxes and fees
The Weldon Hotel
A living room with a sofa, armchair, and glass coffee table. There are two lamps on side tables and a window with curtains.

5. Portland 1-bedroom with enclosed porch & parking

Portland 1-bedroom with enclosed porch & parking
Deering Center
8.2 out of 10, Very good, (16 reviews)
"Easy to get to, and a great night's sleep.Want to stay in Portland but in a quiet neighborhood?-Grab this spot!"
United States
Cricket C.
$109 nightly
The price is $111
Oct 22 - Oct 23
Total with taxes and fees
Portland 1-bedroom with enclosed porch & parking
A multi-story building with a stone facade, large windows, and a corner entrance.

6. Evalina Hotel

Evalina Hotel
2.5 star property
Downtown Portland
10.0 out of 10, Exceptional, (15 reviews)
"This is a very nice hotel in a great location. It’s new and wonderfully appointed. Everything about it is first class."
United States
Rick
$398 nightly
The price is $434
Nov 17 - Nov 18
Total with taxes and fees
Evalina Hotel
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, (41 reviews)
"Overall a pleasing stay."
United States
Mallory D.
$433 nightly
The price is $471
Oct 19 - Oct 20
Total with taxes and fees
Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
Exterior

8. Ocean View East End Studio in a Historic Victorian

Ocean View East End Studio in a Historic Victorian
Portland
9.8 out of 10, Exceptional, (114 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.
$428 nightly
The price is $467
Oct 19 - Oct 20
Total with taxes and fees
Ocean View East End Studio in a Historic Victorian
A coastal view with a house, a tree, and a beach.

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

Willard By the Sea - 30 ft to the beach- 2nd floor
Willard
10.0 out of 10, Exceptional, (15 reviews)
"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."
United States
Gerald B.
$526 nightly
The price is $553
Nov 17 - Nov 18
Total with taxes and fees
Willard By the Sea - 30 ft to the beach- 2nd floor
A modern kitchen with a central island, two stools, skylights, and a view of the outdoors.

10. East End Guesthouse

East End Guesthouse
Munjoy Hill
10.0 out of 10, Exceptional, (5 reviews)
"Fabulous stay!! Felt like we were living in a Crate & Barrel catalog. Great location. "
United States
Ashleigh F.
$369 nightly
The price is $402
Oct 27 - Oct 28
Total with taxes and fees
East End Guesthouse
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
9.8 out of 10, Exceptional, (38 reviews)
"Great property. Cute place. Note that there are very steep steps to get into the place, which is a conveyed attic."
United States
Greg Z.
$265 nightly
The price is $289
Oct 19 - Oct 20
Total with taxes and fees
Sunny Spot with Private Parking.
A bedroom with a wooden bed, a nightstand, a bench, a chair, and a ceiling with a light fixture.

12. Studio Apartment near downtown Walkable!

Studio Apartment near downtown Walkable!
West Bayside
8.6 out of 10, Excellent, (22 reviews)
"We had a great stay in Portland! The place was just as described and the hosts were easy to communicate with. A good place for a couple nights within walking distance of all Portland has to offer."
United States
Lucy T.
$149 nightly
The price is $151
Nov 1 - Nov 2
Total with taxes and fees
Studio Apartment near downtown Walkable!
A modern kitchen with a dining area, featuring a round table, chairs, and a hanging light fixture.

13. 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, (86 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.
$470 nightly
The price is $512
Oct 22 - Oct 23
Total with taxes and fees
Elegant condo - walk to Portland's best restaurants & Old Port
A street lined with buildings, one with a red door and a sign that reads "MINATO".

14. Glorious getaway on Portland's Eastern Promenade.

Glorious getaway on Portland's Eastern Promenade.
Munjoy Hill
9.8 out of 10, Exceptional, (189 reviews)
"The property is well equipped for a long weekend. Parking was convenient. The location offered a quiet place to stay just minutes from Portland’s bustling commercial corridors. Will definitely look to book again on our next visit."
United States
William
$370 nightly
The price is $403
Nov 6 - Nov 7
Total with taxes and fees
Glorious getaway on Portland's Eastern Promenade.
A bedroom with a bed, a nightstand, a lamp, a door, and a staircase.

15. Great suburban location close to town!

Great suburban location close to town!
Deering Center
9.4 out of 10, Exceptional, (3 reviews)
"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 black console table with a mirror above it, a lamp, and a potted plant beside it.

16. 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.
$306 nightly
The price is $334
Nov 1 - Nov 2
Total with taxes and fees
Peaceful & minutes from the Old Port with private parking
A beach with a wooden chair and a small building in the background.

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

Arlie`s Digs! - One Block To Willard Beach!
Willard Beach
10.0 out of 10, Exceptional, (72 reviews)
"Property manager was very kind but a little hard to get a hold of. Owner of the property was amazing and in contact immediately. The house is quaint, cute and perfect for a beautiful stay on the coast. We enjoyed the location more than anything. The owners left a binder with a lot of very helpful information for restaurants, stores, etc. If you want to stay in the area, you can walk almost anywhere. All in all we loved our stay and would return."
United States
James
$444 nightly
The price is $484
Nov 9 - Nov 10
Total with taxes and fees
Arlie`s Digs! - One Block To Willard Beach!
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

NEW 1 BDR-Heart of Munjoy Hill
Munjoy Hill
10.0 out of 10, Exceptional, (15 reviews)
"Fantastic little spot. Great location and easy to find parking even if not using what is reserve. Home had everything necessary for a stay. Hosts were prompt with communication."
United States
Susan
$385 nightly
The price is $420
Oct 20 - Oct 21
Total with taxes and fees
NEW 1 BDR-Heart of Munjoy Hill
A wide beach with people walking and a few dogs.

19. THE RALEIGH BnB APARTMENT SELF CHECK-IN / Free Off-Street Parking

THE RALEIGH BnB APARTMENT SELF CHECK-IN / Free Off-Street Parking
Munjoy Hill
10.0 out of 10, Exceptional, (5 reviews)
"Great place, so close to everything and a clean, quiet spot to sleep."
United States
Dan K.
$393 nightly
The price is $428
Oct 19 - Oct 20
Total with taxes and fees
THE RALEIGH BnB APARTMENT SELF CHECK-IN / Free Off-Street Parking
A room with a ceiling fan, a framed plant artwork, a blue sofa, and a wooden table.

20. 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.
$265 nightly
The price is $289
Nov 4 - Nov 5
Total with taxes and fees
Charming 2-bedroom apartment with AC, WiFi in fabulous Portland
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

Hampton Inn Portland Downtown - Waterfront

Hampton Inn Portland Downtown - Waterfront

10/10 Excellent
"Perfect location to Commercial Street, dining and shopping. Perfect for families. Excellent experience!"
Ashli 3-night trip
Posted 1 hour ago
Hampton Inn Portland Downtown - Waterfront

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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