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Great Diamond Island Holiday Rentals

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Check prices for these dates

In two weeks
3 Oct - 5 Oct
In one month
17 Oct - 19 Oct
In two months
14 Nov - 16 Nov
In three months
12 Dec - 14 Dec

Holiday Rentals in Great Diamond Island

Our top choices for Great Diamond Island holiday rentals

Elegant and efficient Island home 4 miles from downtown Portland
Outdoor dining

Elegant and efficient Island home 4 miles from downtown Portland

9.0 out of 10, Wonderful, (2)
"An ideal home away from home at our most favorite place in Maine. Plenty of extra touches to make guests feel welcome and comfortable. Owner is quick to respond to any questions, and went well above-and-beyond to help us out when we experienced an unforeseen situation. I am so very grateful! I hope we can book this wonderful home again next summer. Thank you!"
Elegant and efficient Island home 4 miles from downtown Portland
The Weldon Hotel
Living area

The Weldon Hotel

4.5 star property
9.8 out of 10, Exceptional, (78)
"Absolutely beautiful place to stay. "
The price is HK$2,458
HK$3,263 total
includes taxes & fees
1 Oct - 2 Oct
The Weldon Hotel
Sensational Beachfront Property Old Orchard Beach, with indoor elevator
Outdoor dining

Sensational Beachfront Property Old Orchard Beach, with indoor elevator

9.6 out of 10, Exceptional, (63)
"Our stay was perfect. The house allowed for us to sleep 17 people comfortably, eat together, cook in teams for a progressive dinner and spread out all at the same time. Jason was quick to answer questions, and he provided excellent suggestions for places to eat and shop. We could not be more pleased with our stay. Thank you, Jason!!"
The price is HK$5,438
HK$10,650 total
includes taxes & fees
16 Sept - 17 Sept
Sensational Beachfront Property Old Orchard Beach, with indoor elevator
68 East Grand Ave
Private kitchen

68 East Grand Ave

3.0 star property
8.6 out of 10, Excellent, (9)
"Property was very nice and close to the beach. Would stay there again. The front desk was extremely helpful as well. "
68 East Grand Ave
Bright and airy condo with beachfront access and walkable entertainment nearby
Fridge, microwave, oven, stovetop

Bright and airy condo with beachfront access and walkable entertainment nearby

6.8 out of 10, (3)
"Not a bad spot. Just don't expect too much in the way of frills and be prepared to be flexible with sleeping/parking arrangements."
Bright and airy condo with beachfront access and walkable entertainment nearby
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach
On the beach

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

10.0 out of 10, Exceptional, (227)
"Beautiful views, very clean and enjoyed the oceanside vibe both inside and out! Easy walk to general store and walkable to Giant Stairs trail and Cedar Beach."
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach
Grand Victorian on the Beach, Summer
Fridge, microwave, oven, stovetop

Grand Victorian on the Beach, Summer

9.8 out of 10, Exceptional, (78)
"Wonderful spot with great accommodations! Would definitely stay again!"
Grand Victorian on the Beach, Summer
Cozy and Quiet Home One Bedroom Private Bathroom in Portland Maine. NOT KITCHEN.
1 bedroom, in-room safe, free WiFi, bed sheets

Cozy and Quiet Home One Bedroom Private Bathroom in Portland Maine. NOT KITCHEN.

2.0 star property
10.0 out of 10, Exceptional, (2)
"The property was as described, clean, and in a quiet neighborhood. Conveniently located to many local attractions. Check in and check out process was smooth. Overall enjoyed my stay very much. "
Cozy and Quiet Home One Bedroom Private Bathroom in Portland Maine. NOT KITCHEN.
Beach House ∆ Prime Location ∆ Steps to the Ocean
3 bedrooms, desk, iron/ironing board, travel cot

Beach House ∆ Prime Location ∆ Steps to the Ocean

10.0 out of 10, Exceptional, (48)
"Great location. House was clean. "
The price is HK$1,421
HK$4,169 total
includes taxes & fees
25 Sept - 26 Sept
Beach House ∆ Prime Location ∆ Steps to the Ocean
Gorgeous ocean-front home with stunning beach views
On the beach

Gorgeous ocean-front home with stunning beach views

9.4 out of 10, Exceptional, (115)
"Loved the area. Close to shops and dining. Beach is absolutely beautiful. Perfect place for families."
Gorgeous ocean-front home with stunning beach views
Private, 2nd Floor Cottage with Wonderful Ocean Views- Perfect for Families!
Beach

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

9.8 out of 10, Exceptional, (44)
"This place is a real gem. Really clean, well equipped and for our two kids it was perfect (toys inside and playground in the yard. The host is very kind and very quick to fulfill our needs. Thanks again!"
Private, 2nd Floor Cottage with Wonderful Ocean Views- Perfect for Families!
Cozy Coastal Condo with Parking – Walk to Beach & Town
Beach nearby

Cozy Coastal Condo with Parking – Walk to Beach & Town

2.0 star property
8.6 out of 10, Excellent, (13)
"The place was clean and spacious enough for our family of 4. A simple place within one block of the ocean. Can’t beat that! When we had an issue with WiFi, they responded promptly and all was rectified very quickly. Easy access upon arrival and clear directions about departure. Would recommend ."
Cozy Coastal Condo with Parking – Walk to Beach & Town
Spectacular Oceanfront Property Offering Bold Panoramic Views of Saco Bay !
Terrace/patio

Spectacular Oceanfront Property Offering Bold Panoramic Views of Saco Bay !

10.0 out of 10, Exceptional, (39)
"The view is beautiful and has everything you need "
Spectacular Oceanfront Property Offering Bold Panoramic Views of Saco Bay !
350 Yards to the beach. Pet friendly!
Beach

350 Yards to the beach. Pet friendly!

8.0 out of 10, Very good, (34)
"Clean, easy access to everything! Fantastic stay will come again! Thank you!"
The price is HK$2,139
HK$3,443 total
includes taxes & fees
20 Sept - 21 Sept
350 Yards to the beach. Pet friendly!
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator
Interior

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

9.8 out of 10, Exceptional, (219)
"We stayed off season to just get away. The beach view is really nice. We went to the restaurant downstairs for food and live music. Very convenient! Place was clean. "
The price is HK$1,361
HK$2,646 total
includes taxes & fees
14 Oct - 15 Oct
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator
Ocean Front Penthouse suite, Luxurious 2-bedroom,1350 sqft,2 decks, A++ location
Interior

Ocean Front Penthouse suite, Luxurious 2-bedroom,1350 sqft,2 decks, A++ location

10.0 out of 10, Exceptional, (23)
"The perfect luxury location in the heart of all the action! Highly recommend!!! The property manger is awesome, great communication!! "
The price is HK$2,295
HK$4,392 total
includes taxes & fees
16 Sept - 17 Sept
Ocean Front Penthouse suite, Luxurious 2-bedroom,1350 sqft,2 decks, A++ location
New 2-bedroom cabin with WiFi, AC in delightful Old Orchard Beach
Interior

New 2-bedroom cabin with WiFi, AC in delightful Old Orchard Beach

9.8 out of 10, Exceptional, (7)
New 2-bedroom cabin with WiFi, AC in delightful Old Orchard Beach
Charming 2-Bedroom Cottage in Peaceful Old Orchard Beach with WiFi, AC
Smart TV

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

10.0 out of 10, Exceptional, (7)
Charming 2-Bedroom Cottage in Peaceful Old Orchard Beach with WiFi, AC
100 feet from the ocean 3 bedroom cottage 420 friendly
Beach nearby, sun-loungers, beach towels

100 feet from the ocean 3 bedroom cottage 420 friendly

8.4 out of 10, Very good, (20)
"Our family of 5 stayed here with our dog. This place has it all and we wanted for nothing. Stocked with towels, everything you would need in the kitchen. There’s even a washer and dryer on site. Right next the beach and a short walk to the pier. It was very clean and well taken care of. We will definitely be back!"
100 feet from the ocean 3 bedroom cottage 420 friendly
Full sized home
Interior

Full sized home

9.8 out of 10, Exceptional, (39)
"The house was lovely. Very comfortable place. Within 15- 20 mins to a store or restaurants."
The price is HK$1,556
HK$2,790 total
includes taxes & fees
15 Oct - 16 Oct
Full sized home
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

Canopy by Hilton Portland Waterfront

Canopy by Hilton Portland Waterfront

10/10 Excellent
"Great "
Earl 2-night trip
Posted 5 days ago
Canopy by Hilton Portland Waterfront

Find out more about Great Diamond Island

Find out more about Great Diamond Island

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