Photo by Robbie Martin

Search Vacation Homes in Great Diamond Island

  • Plan, book, stay with confidence
  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 468 Vacation Homes in Great Diamond Island with updated reviews, rates, and availability.

New Well Built Elegant Home on the Water 2 miles to Freeport, 9 to Portland!

9.8 out of 10, Exceptional, (174)
"Great house, big enough for our family group ranging from 1 year old to 70 year old. :) Home was clean & spacious & cozy - with a beautiful view. "
New Well Built Elegant Home on the Water 2 miles to Freeport, 9 to Portland!

Stille Wasser, Quiet, secluded spot on Saco River with Dock (Boat lift option)

9.6 out of 10, Exceptional, (71)
"Enjoyed this peaceful home and property. "
Stille Wasser, Quiet, secluded spot on Saco River with Dock (Boat lift option)

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

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

Spacious & Sunny 4 Bedroom Close to Downtown, hot tub

9.2 out of 10, Wonderful, (30)
"We had a great time. Nate made check in/check out very easy and the location is great. Would recommend staying here!"
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub

Charming Cottage Steps to Pine Point Bch - 1 mile OOB outside Scarborough w/ AC

9.6 out of 10, Exceptional, (26)
"Repeat visit. Short walk to beach. Convenient to stores if you want to shop. Cottage comfortable. We’ll be back!"
Charming Cottage Steps to Pine Point Bch - 1 mile OOB outside Scarborough w/ AC

Beautiful Combo Home Located in Downtown Portland - Close to the Beach

8.8 out of 10, Excellent, (15)
"Convenient to walking to town , great restaurants in the area for breakfast & dinner, house was perfect, comfortable, well maintained great off street parking and had everything we could ever had needed."
Beautiful Combo Home Located in Downtown Portland - Close to the Beach

Lofty cottage

9.4 out of 10, Exceptional, (39)
"We really enjoyed our time here has a beautiful view of the ocean. Had all the things needed to kayak and go out on the water. Nice and secluded. Had a fire pit, which was lovely to turn on In the evening. Would recommend this place and stay again"
The price is AED 735
AED 1,337 total
includes taxes & fees
27 Nov - 28 Nov
Lofty cottage

Clean, renovated Camp Ellis classic

10.0 out of 10, Exceptional, (3)
"Host was fabulous to quickly respond to any questions we had. We were close to the pier, small beach (maybe a block or less!) and Old Orchard Beach just 10 minutes away. House had all we needed for our stay and was clean and comfortable. We completely loved our visit! "
Clean, renovated Camp Ellis classic

Charming ocean-view cottage just 10 minutes from downtown Freeport shops

2.0 star property
Charming ocean-view cottage just 10 minutes from downtown Freeport shops

The Moonglow! A beautiful ocean view house in Biddeford!

9.8 out of 10, Exceptional, (93)
"We had a wonderful time! Beautiful location.. very comfortable accommodations!! "
The Moonglow! A beautiful ocean view house in Biddeford!

3 Story Historic Landmark - Walk to All! West End, Dog-Friendly, 2 King Beds

8.4 out of 10, Very Good, (6)
"We booked Nick’s place for myself, husband, 3 year old & my in-laws before we all left Portland. We were able to get an early check in, which was great because I felt horrible with a migraine & the heat was unbearable. The home has a lot of character. I would stay there again!"
The price is AED 1,342
AED 2,724 total
includes taxes & fees
1 Dec - 2 Dec
3 Story Historic Landmark - Walk to All! West End, Dog-Friendly, 2 King Beds

Rise & Shine on Sebago Lake

9.8 out of 10, Exceptional, (8)
"We wanted a place for extended family to be together for a family wedding at Caswell Farms There was room for everyone and a wonderful Lake Sebago view from multiple rooms We enjoyed kayaking, hot tub, wonderful kitchen amenities for a lobster boil Conveniently located to stores and restaurants Wonderful home and memories made!! Attentive hosts and maintenance staff Loved it!"
Rise & Shine on Sebago Lake

Shady Potts Point Cottage Cooled by Ocean Breezes

9.6 out of 10, Exceptional, (77)
"Great stay in very clean house in a very quiet ocean side community. Perfect getaway!"
Shady Potts Point Cottage Cooled by Ocean Breezes

Lakeside Living w\sandy beach, gas fireplace -easy 25 minute commute to Portland

10.0 out of 10, Exceptional, (23)
"My family of three really enjoyed our stay! My 5 year old enjoyed playing with the different toys and puzzles at the house. Photos are accurate and the beds were very comfortable. The kitchen was well stocked for making meals. My son liked having his own room and bathroom upstairs. We spent a lot of time outside and had several fires! Visited Pineland Farms (loved seeing the cows up close!) and the Maine Wildlife Park (1000 ft from the house). Also loved that it was dog friendly so our pup...
Lakeside Living w\sandy beach, gas fireplace -easy 25 minute commute to Portland

Enjoy Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary

9.8 out of 10, Exceptional, (68)
"Great house very comfortable and well appointed. Very roomy for our entire family. Nice to have en suite bathrooms with all the bedrooms. The host was very good with communication. Located on a busy road and the driveway is on a curve which made it a little challenging entering and exiting the property. "
Enjoy Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary

Spectacular Waterfront Retreat Close To Portland!

10.0 out of 10, Exceptional, (46)
"Spent 2 glorious fall weeks at this West Bath property. This older, well updated house nicely accommodated the two of us. It was very comfortable and clean. We had everything we needed. There were plenty of dishes and flatware. We cooked in for most meals. There are black out curtains in the main bedroom, so you can really sleep in if you want to! We did! The backyard views are wonderful. Jennie’s Nubble has an active eagles nest. Lobster boats and sail boats were frequently in the area. The...
Spectacular Waterfront Retreat Close To Portland!

23 Cottage Ave Kinney Shores 3 Bedroom,2 Bath, Cottage, 7 Miles of Beachfront

9.8 out of 10, Exceptional, (9)
"So much phun. Seconds from the beach, great location and property was perfect for a family get away. Not fancy, but effective "
23 Cottage Ave Kinney Shores 3 Bedroom,2 Bath, Cottage, 7 Miles of Beachfront

Biddeford Retreat w/ Deck, Grill & Ocean Views!

7.2 out of 10, Good, (19)
"House was all we expected- and more. Owners were delightful to meet but could have been a bit better at answering questions before our trip. Overall, it was a great experience!"
Biddeford Retreat w/ Deck, Grill & Ocean Views!

beautiful home away from home in Orchard Beach

7.8 out of 10, Good, (9)
"Wonderful!..we all had our own comfy bedrooms…The kitchen was fully stocked with everything you might need..Loved the back porch with tv and couches..Big back yard with fire pit which we used twice.Ahmad even gave us the wood.Very clean…and the air conditioning was greatly appreciated.Ahmad was the perfect host. Warning…..owner has a dog on the premises if you’re bringing a pet…and watch out…the hot water is scalding!.If you’re looking for a vacation home near the beach but in a quiet area,this...
beautiful home away from home in Orchard Beach

Cottage by the Sea - Steps to Crescent Beach, a Quick Drive to Portland

10.0 out of 10, Exceptional, (19)
"Our stay was memorable and so enjoyable. There were 5 of us, 4 adults and 1 child. The location is in a nice little neighborhood, only steps from Crescent Beach. We could sit on our deck and see the ocean and sleep by the sounds of the waves. This property has so much to offer with three bedrooms, one of which is downstairs for this older stair challenged lady. It has three parking spots and a lovely fenced yard for the kids to play in. The cottage was very clean and the owner has it stocked...
Cottage by the Sea - Steps to Crescent Beach, a Quick Drive to 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.
Don't see what you're looking for?
See all available properties in Great Diamond Island
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Great Diamond Island

Beachfront Luxury Grand Victorian Condo (Primetime View directly down the pier)

9.8 out of 10, Exceptional, (115)
"Very relaxing getaway."
Beachfront Luxury Grand Victorian Condo (Primetime View directly down the pier)

Gorgeous ocean-front home with stunning beach views

9.6 out of 10, Exceptional, (98)
"Great oceanfront location for a relaxing girls getaway. We enjoyed walking the beach and collecting shells. Great location to start from to see other cities in the area. Best part was watching the sunrise in the morning from the balcony. "
Gorgeous ocean-front home with stunning beach views

Artsy Apt/Private Rooftop Deck!/Old Port Arts Dist

10.0 out of 10, Exceptional, (35)
"Beautiful place , had everything you need . Very comfortable bed . Great shower & Kitchen . Also a great location! "
Artsy Apt/Private Rooftop Deck!/Old Port Arts Dist
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.