Great Diamond Island Vacation Rentals

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Nov 30 - Dec 1
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Dec 1 - Dec 2
Next weekend
Dec 5 - Dec 7
In two weeks
Dec 12 - Dec 14

Vacation Rentals in Great Diamond Island

Pool
Cozy Coveside Island Retreat

Vacation Home in Portland

Cozy Coveside Island Retreat
Deluxe Suite, 1 King Bed | Living area | LCD TV, Netflix, streaming services, music library
The Weldon Hotel

Aparthotel in Downtown Portland

4.5 star property
9.8 out of 10, Exceptional, (88)
"Loved this place and would definitely stay here next time we go back."
United States
Eleni
$246 nightly
The price is $262
Dec 8 - Dec 9
Total with taxes and fees
The Weldon Hotel
Beach
Private, 2nd Floor Cottage with Wonderful Ocean Views- Perfect for Families!

Vacation Home in Old Orchard Beach

9.8 out of 10, Exceptional, (45)
"Excellent family stay. Backyard is nice and shaded, you can see the ocean from the house and amenities are great. "
United States
Danielle N.
Private, 2nd Floor Cottage with Wonderful Ocean Views- Perfect for Families!
On the beach
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

Vacation Home in Bailey Island

10.0 out of 10, Exceptional, (233)
"Tremendous stay, great property and host."
United States
Curtis G.
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach
Outdoor dining
Sensational Beachfront Property Old Orchard Beach, with indoor elevator

Vacation Home in Old Orchard Beach

9.6 out of 10, Exceptional, (67)
"In one word AMAZING! We rented this property to gather our immediate family, adult children and grandchildren. We had a tragedy in our family as my oldest son was killed, this made our once close family, split apart. This property was so beautiful and such a happy place to be that my prayers were answered my family began the healing process. The location and the views one could not be unhappy. Thank you Jason for helping to make the stay amazing!"
United States
Helen F.
$1,597 nightly
The price is $1,741
Dec 5 - Dec 6
Total with taxes and fees
Sensational Beachfront Property Old Orchard Beach, with indoor elevator
Beach nearby
Perfect for Families & friends re-unions! Outdoor Hot Tub, 50 yards to the beach!

Vacation Home in Old Orchard Beach

9.8 out of 10, Exceptional, (97)
"The location was perfect and the house was exceptional. The host and property manager were very responsive and helpful. Would definitely recommend a stay!"
United States
Kathleen C.
$1,025 nightly
The price is $1,117
Dec 3 - Dec 4
Total with taxes and fees
Perfect for Families & friends re-unions! Outdoor Hot Tub, 50 yards to the beach!
1 bedroom, bed sheets
Studio Unit Walkable Everywhere

Apartment in West Bayside

5.8 out of 10, (7)
"We didn't stay there at all. Canceled reservation "
United States
Dianne
$154 nightly
The price is $156
Dec 1 - Dec 2
Total with taxes and fees
Studio Unit Walkable Everywhere
Private kitchen
Spacious 7-bedroom house with WiFi and AC in fabulous Pine Point Scarborough

Vacation Home in Grand Beach

2.0 star property
9.0 out of 10, Wonderful, (17)
"Incredibly wonderful beach house. Plenty of room for 8 adults, 6 children. Would recommend for any group with lots of ages and preferences. Helped to create wonderful family reunion."
United States
Ina-Lee B.
Spacious 7-bedroom house with WiFi and AC in fabulous Pine Point Scarborough
Smart TV
Charming 2-Bedroom Cottage in Peaceful Old Orchard Beach with WiFi, AC

Cabin in Old Orchard Beach

9.8 out of 10, Exceptional, (12)
"Walking distance to the board walk. Clean and just enough space for 4 of us. Had everything we needed plus plenty of towels! "
United States
Natalia R.
Charming 2-Bedroom Cottage in Peaceful Old Orchard Beach with WiFi, AC
Fridge, microwave, oven, stovetop
Private Entrance Residential Portland

Apartment in Deering Center

9.2 out of 10, Wonderful, (5)
"Great location for seeing the Portland Head Lighthouse. Comfortable bed."
United States
Michelle S.
Private Entrance Residential Portland
Fridge, microwave, oven, stovetop
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach

Cottage in Old Orchard Beach

9.8 out of 10, Exceptional, (65)
"Place was great and fenced in backyard for our dog. "
United States
Billy N.
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach
Fridge, oven, stovetop, coffee/tea maker
Updated Long Island Maine Cottage

Cottage in Long Island

10.0 out of 10, Exceptional, (7)
"Great island house! Loved how stocked the kitchen was, we had comfortable beds and even beach chairs and cooler. We would definitely stay here again. "
United States
Serra C.
Updated Long Island Maine Cottage
Fridge, microwave, oven, stovetop
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

Vacation Home in East Deering

10.0 out of 10, Exceptional, (65)
"Nice stay. Good amenities. "
United States
Laura H.
$986 nightly
The price is $1,074
Dec 1 - Dec 2
Total with taxes and fees
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
Fridge, microwave, oven, stovetop
Gorgeous and Unique New England Beach House: Panoramic Views of Saco Bay!

Vacation Home in Saco

10.0 out of 10, Exceptional, (104)
"Would love to stay here again!! "
United States
Michelle E.
Gorgeous and Unique New England Beach House: Panoramic Views of Saco Bay!
Interior
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator

Condo in Old Orchard Beach

9.8 out of 10, Exceptional, (227)
"The view off the deck was breathtaking "
United States
Raymond
$310 nightly
The price is $338
Dec 1 - Dec 2
Total with taxes and fees
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator
Fridge, microwave, oven, stovetop
1 room luxury ocean front studio cottage

Apartment in Harpswell

9.6 out of 10, Exceptional, (170)
"Very clean beautiful view we definitely enjoyed ourselves "
United States
Ilona F.
1 room luxury ocean front studio cottage
Outdoor dining
Spectacular Beachfront Condo-Watch sunrise from deck overlooking beach.

Condo in Old Orchard Beach

9.8 out of 10, Exceptional, (36)
"Great spot...everything was great "
United States
Frank R.
Spectacular Beachfront Condo-Watch sunrise from deck overlooking beach.
Property grounds
Charming 2-bedroom house with AC, WiFi in lovely Falmouth

Vacation Home in Falmouth

8.8 out of 10, Excellent, (6)
"We had a wonderful stay. Nice comfortable camp. We enjoyed swimming in the lake. "
United States
Darcie B.
Charming 2-bedroom house with AC, WiFi in lovely Falmouth
Fridge, microwave, oven, stovetop
Alluring 2-Bedroom Cottage in Delightful Old Orchard Beach with WiFi, AC

Cottage in Old Orchard Beach

9.6 out of 10, Exceptional, (12)
"We recently rented this for a quick family vacation and it exceeded our expectations. Can't wait to go back next summer!"
United States
Jennifer
Alluring 2-Bedroom Cottage in Delightful Old Orchard Beach with WiFi, AC
TV
In-town no frills 2 bedroom apt

Apartment in West Bayside

8.6 out of 10, Excellent, (16)
"Host was very accommodating. Apartment worked well for. Description accurate. Would stay again."
United Kingdom
Martha F.
$154 nightly
The price is $156
Dec 1 - Dec 2
Total with taxes and fees
In-town no frills 2 bedroom apt
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

DoubleTree by Hilton Hotel Portland

DoubleTree by Hilton Hotel Portland

10/10 Excellent
"Spacious room"
Kevin J 1-night trip
Posted 19 hours ago
DoubleTree by Hilton Hotel Portland

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 $156 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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