Great Diamond Island Vacation Rentals

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Vacation Rentals in Great Diamond Island

Cozy Coveside Island Retreat

Portland
Cozy Coveside Island Retreat

The Weldon Hotel

4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (87)
"Loved this place and would definitely stay here next time we go back."
United States
Eleni
$238 nightly
The price is $253
Nov 29 - Nov 30
Total with taxes and fees
The Weldon Hotel

New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

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

Private, 2nd Floor Cottage with Wonderful Ocean Views- Perfect for Families!

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!

Sensational Beachfront Property Old Orchard Beach, with indoor elevator

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.
$1,598 nightly
The price is $1,742
Dec 5 - Dec 6
Total with taxes and fees
Sensational Beachfront Property Old Orchard Beach, with indoor elevator

Perfect for Families & friends re-unions! Outdoor Hot Tub, 50 yards to the beach!

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.
$1,027 nightly
The price is $1,119
Dec 3 - Dec 4
Total with taxes and fees
Perfect for Families & friends re-unions! Outdoor Hot Tub, 50 yards to the beach!

Sunny Modern Oasis in Portland’s Trendy East End

Munjoy Hill
10.0 out of 10, Exceptional, (62)
"Cozy, clean and quiet, within short walking distance to restaurants, coffee shops, breweries, distilleries and shopping. "
United States
Jane
Sunny Modern Oasis in Portland’s Trendy East End

Gorgeous ocean-front home with stunning beach views

Old Orchard Beach
9.4 out of 10, Exceptional, (126)
"Loved the area. Close to shops and dining. Beach is absolutely beautiful. Perfect place for families."
United States
Victoria H.
Gorgeous ocean-front home with stunning beach views

Spacious 7-bedroom house with WiFi and AC in fabulous Pine Point Scarborough

2.0 star property
Grand Beach
9.0 out of 10, Wonderful, (17)
"Great location. Beautiful view. Peaceful part of the beach. "
United States
Kristi N.
Spacious 7-bedroom house with WiFi and AC in fabulous Pine Point Scarborough

Studio Unit Walkable Everywhere

West Bayside
5.8 out of 10, (6)
"We didn't stay there at all. Canceled reservation "
United States
Dianne
$144 nightly
The price is $145
Nov 24 - Nov 25
Total with taxes and fees
Studio Unit Walkable Everywhere

The Dollhouse

Old Orchard Beach
9.2 out of 10, Wonderful, (5)
"Wonderful stay for a small bachelorette party! Right squeeze with 7 girls but great to have the place already decorated. Very close to the pier and lots of stores, restaurants, and places to go around. Host was very friendly and accommodating, answered questions and was flexible with any of our needs!"
United States
Margaret D.
$686 nightly
The price is $748
Nov 24 - Nov 25
Total with taxes and fees
The Dollhouse

Private Entrance Residential Portland

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

Charming 2-Bedroom Cottage in Peaceful Old Orchard Beach with WiFi, AC

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

Gorgeous and Unique New England Beach House: Panoramic Views of Saco Bay!

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!

In-town no frills 2 bedroom apt

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
Nov 24 - Nov 25
Total with taxes and fees
In-town no frills 2 bedroom apt

Charming Studio apartment with WiFi, AC in welcoming Portland

Munjoy Hill
9.6 out of 10, Exceptional, (11)
"Easy check in and check out. Great neighborhood with good food and coffee close by. "
United States
Ryan W.
$211 nightly
The price is $230
Nov 28 - Nov 29
Total with taxes and fees
Charming Studio apartment with WiFi, AC in welcoming Portland

Beautiful Oceanfront House- Stunning Water Views

Harpswell
9.4 out of 10, Exceptional, (23)
"We loved our stay! Gorgeous view, lots of thoughtful little amenities. The home was extremely clean and the host was just lovely. "
United States
Catherine O.
Beautiful Oceanfront House- Stunning Water Views

Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach

Old Orchard Beach
9.8 out of 10, Exceptional, (64)
"Place was great and fenced in backyard for our dog. "
United States
Billy N.
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach

Updated Long Island Maine Cottage

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

1 room luxury ocean front studio cottage

Harpswell
9.6 out of 10, Exceptional, (169)
"Very clean beautiful view we definitely enjoyed ourselves "
United States
Ilona F.
1 room luxury ocean front studio cottage
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 $145 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.