Photo by Robbie Martin

Great Diamond Island Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Nov 12 - Nov 13
Tomorrow
Nov 13 - Nov 14
This weekend
Nov 14 - Nov 16
Next weekend
Nov 21 - Nov 23

Vacation Rentals in Great Diamond Island

Pool
Cozy Coveside Island Retreat

Cozy Coveside Island Retreat

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

The Weldon Hotel

4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (86)
"Absolutely beautiful place to stay. "
United States
James
The price is ￥28,441
￥42,562 total
includes taxes & fees
Dec 7 - Dec 8
The Weldon Hotel
On the beach
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

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

Bailey Island
10.0 out of 10, Exceptional, (232)
"Tremendous stay, great property and host."
United States
Curtis G.
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach
Beach
Private, 2nd Floor Cottage with Wonderful Ocean Views- Perfect for Families!

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

Old Orchard Beach
9.8 out of 10, Exceptional, (45)
"😍😍😍"
United States
Sara L.
Private, 2nd Floor Cottage with Wonderful Ocean Views- Perfect for Families!
Terrace/patio
The Moonglow! A beautiful ocean view house in Biddeford!

The Moonglow! A beautiful ocean view house in Biddeford!

Biddeford
9.8 out of 10, Exceptional, (124)
"House was beautiful! Comfy beds, amazing views,great location!"
United States
Katherine C.
The Moonglow! A beautiful ocean view house in Biddeford!
Outdoor dining
Sensational Beachfront Property Old Orchard Beach, with indoor elevator

Sensational Beachfront Property Old Orchard Beach, with indoor elevator

Old Orchard Beach
9.6 out of 10, Exceptional, (67)
"Made a great place for a business retreat. WiFi worked well and we had plenty of space to spread out."
United States
dan b.
The price is ￥92,282
￥191,603 total
includes taxes & fees
Nov 18 - Nov 19
Sensational Beachfront Property Old Orchard Beach, with indoor elevator
Fridge, microwave, oven, stovetop
Gorgeous and Unique New England Beach House: Panoramic Views of Saco Bay!

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

Saco
10.0 out of 10, Exceptional, (104)
"Such a beautiful home in an amazing location! "
United States
Michelle H.
Gorgeous and Unique New England Beach House: Panoramic Views of Saco Bay!
Beach nearby
2 min walk to the beach. Pet friendly condo

2 min walk to the beach. Pet friendly condo

Old Orchard Beach
8.2 out of 10, Very Good, (41)
"Over all it was good, bathroom was off bedroom, not convenient for other guest staying on futon in living room. Backyard for dogs was very small, but enough space for the pups to do their duty. In all it worked for the few days we were there!"
United States
Cindy H.
2 min walk to the beach. Pet friendly condo
Smart TV
Charming 2-Bedroom Cottage in Peaceful Old Orchard Beach with WiFi, AC

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
1 bedroom, bed sheets
Studio Unit Walkable Everywhere

Studio Unit Walkable Everywhere

West Bayside
5.8 out of 10, (6)
"Great, comfortable place to stay. The location is super walkable. There are several bars/restaurants very close, and other areas are close enlighten to walk to as well (I.e. Congress Street). Commercial is a bit of a walk, but if you’re like us and love to walk a new area. It’s not that far. The bed is comfortable and the place was very clean. Communication was great. We would stay here again!"
United States
Anonymous traveler
The price is ￥10,515
￥21,577 total
includes taxes & fees
Nov 13 - Nov 14
Studio Unit Walkable Everywhere
Beach
Little Miss Cottages - Two Bedroom Cottage

Little Miss Cottages - Two Bedroom Cottage

Old Orchard Beach
9.0 out of 10, Wonderful, (4)
"It was a very enjoyable weekend stay. Cottage was clean and comfortable. The water heater was a bit noisy as was the traffic noise at the front bedroom, but otherwise, could not have ask for more. Perfect access to beach. "
United States
Lynne M.
The price is ￥21,476
￥45,756 total
includes taxes & fees
Nov 30 - Dec 1
Little Miss Cottages - Two Bedroom Cottage
Interior
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator

Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator

Old Orchard Beach
9.8 out of 10, Exceptional, (224)
"The view off the deck was breathtaking "
United States
Raymond
The price is ￥26,961
￥52,225 total
includes taxes & fees
Nov 13 - Nov 14
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator
Fridge, microwave, oven, stovetop
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach

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

Old Orchard Beach
9.8 out of 10, Exceptional, (64)
"My wife and I both enjoyed our stay and found the unit to be very cute, clean and comfortable. The owners were also quite nice and communicated very well whenever we reached out to them. We had a great stay!"
United States
Russell R.
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach
2 bedrooms, WiFi, bed sheets
The Dollhouse

The Dollhouse

Old Orchard Beach
9.2 out of 10, Wonderful, (5)
"We had a great time! The place was exactly like the pictures. It was clean and had lots of amenities. My only suggestion would have more towels because we had five people and four bath towels. "
United States
Molly D.
The price is ￥69,327
￥115,197 total
includes taxes & fees
Nov 13 - Nov 14
The Dollhouse
TV
In-town no frills 2 bedroom apt

In-town no frills 2 bedroom apt

West Bayside
8.4 out of 10, Very Good, (14)
"Beds were very comfortable. Parking was a little difficult. 3rd floor was a little tough on my 83 year old mother. But it was clean and roomy and close to downtown shopping and touristy attractions."
United States
Betsy Jean
The price is ￥12,132
￥23,194 total
includes taxes & fees
Nov 13 - Nov 14
In-town no frills 2 bedroom apt
On the beach, sun loungers
Best house in Old Orchard Beach..STEPS/BEACH, surf!!!! 4 bedroom

Best house in Old Orchard Beach..STEPS/BEACH, surf!!!! 4 bedroom

Old Orchard Beach
9.8 out of 10, Exceptional, (44)
"Great house with lots of room for a big family. So close to the beach with great views. Great outdoor spaces as well! "
United States
Moria B.
Best house in Old Orchard Beach..STEPS/BEACH, surf!!!! 4 bedroom
Fridge, oven, stovetop, coffee/tea maker
Updated Long Island Maine Cottage

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
Fridge, microwave, oven, stovetop
Private Entrance Residential Portland

Private Entrance Residential Portland

Deering Center
9.2 out of 10, Wonderful, (5)
"Check in was simple. Quaint place. "
United States
Danielle C.
Private Entrance Residential Portland
Beach nearby
Perfect for Families & friends re-unions! Outdoor Hot Tub, 50 yards to the beach!

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

Old Orchard Beach
9.8 out of 10, Exceptional, (97)
"This was the second year that we’ve stayed here. The house is beautiful and we had an amazing time."
United States
jill s.
The price is ￥76,921
￥172,560 total
includes taxes & fees
Dec 3 - Dec 4
Perfect for Families & friends re-unions! Outdoor Hot Tub, 50 yards to the beach!
Private kitchen
Spacious 7-bedroom house with WiFi and AC in fabulous Pine Point Scarborough

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, (16)
"Very responsive host, even got us a pack and play for our youngest! Perfect house for a beach stay! Would stay again! "
United States
Matthew D.
Spacious 7-bedroom house with WiFi and AC in fabulous Pine Point Scarborough
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Great Diamond Island Hotel Reviews

Holiday Inn Portland-By the Bay by IHG

Holiday Inn Portland-By the Bay by IHG

10/10 Excellent
"Everything was great clean rooms clean common spaces staff was pleasant , but the room temperature was set at 71 and I couldn’t cool it any lower than 65 . 65 is way warmer than comfortable to try and sleep. My only other concern was parking , they had a convention of some sort going on so I had to use the over flow parking and that part wasn’t explained very well"
Paul 1-night trip
Posted 22 hours ago
Holiday Inn Portland-By the Bay by IHG

Find out more about Great Diamond Island

Search for holiday rentals in Great Diamond Island on Expedia! You can easily find your home rentals, villas, holiday apartments in Great Diamond Island using one of the methods below:

  • View our selection of featured holiday rentals in Great Diamond Island
  • Use the map to find apartments and other holiday homes in the Great Diamond Island neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Great Diamond Island while they last

Look no further and take a look at our great range of rental properties in Great Diamond Island!