Casco Bay Islands Holiday Rentals

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Holiday Rentals in Casco Bay Islands

Gorgeous ocean-front home with stunning beach views
9.6 out of 10, Exceptional, (88)
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Gorgeous ocean-front home with stunning beach views
Oceanfront Condo! Spectacular Views From Private Large Balcony
9.0 out of 10, Wonderful, (119)
"This has been our fifth year staying in this condo and we are always super happy with the accommodations! Very clean and well taken care of, it’s an incredible spot.. live music you can listen to from the balcony and beautiful views, also so close to everything!"
The price is AU$575
includes taxes & fees
6 Oct - 7 Oct
Oceanfront Condo! Spectacular Views From Private Large Balcony
Quintessential Maine Beach Cottage
10.0 out of 10, Exceptional, (99)
"That we returned for the 3rd year in a row and look forward to a fourth says it all. Perfect location next to salt marsh and literally just a few steps to beach across the street. Couldn't ask for more."
Quintessential Maine Beach Cottage
Little Miss Cottages
2.5 star property
8.4 out of 10, Very good, (81)
"Great location and cute cabins. We have been coming to OOB for years and this is the best pet friendly rental!"
Little Miss Cottages
Appalachee Pond Waterfront Cottage | Decks, Sunroom, Dock with Kayaks & Canoe
9.6 out of 10, Exceptional, (27)
"This house was amazing. It was way better than we expected after looking through the pictures online. The outdoor space and the house itself are beautiful and the pictures do it zero justice. We were worried at first about the lack of AC, but the house cooled right down once we opened the windows let the air in. I highly recommend this place if you’re looking to visit Boothbay. It was so close to the main area, but you couldn’t even tell- it felt like you were immersed in nature."
Appalachee Pond Waterfront Cottage | Decks, Sunroom, Dock with Kayaks & Canoe
Come enjoy 7 miles of beaches in Sunny OOB in this 2 bedroom condo.
8.6 out of 10, Excellent, (55)
"Easy access and check in. The location was just what we wanted with it close to the beach."
The price is AU$546
includes taxes & fees
30 Sept - 1 Oct
Come enjoy 7 miles of beaches in Sunny OOB in this 2 bedroom condo.
Charming 110-year former Inn 10' from the Ocean!
9.8 out of 10, Exceptional, (108)
"We really enjoyed our two weeks stay on Willard Beach. It was wonderful to fall asleep and to awaken to the sound of the ocean. John's place is very special. The beds and the couches and the porch seating are all very comfortable. The shower is wonderful. "
Charming 110-year former Inn 10' from the Ocean!
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub
9.2 out of 10, Wonderful, (29)
"Had a great stay! "
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub
Come enjoy 7 miles of beaches in sunny OOB in this 2 bedroom condo.
7.4 out of 10, Good, (26)
"The location was amazing! Walking distance to the pier, and right by the beach! We enjoyed that it was far enough down from the pier that the beach was a bit less crowded but we were still able to walk downtown. The accommodations are very cute and rustic. Some things could use attention, like paint touch ups and the patio table needs replacing… however these were minor issues and we will be back! "
Come enjoy 7 miles of beaches in sunny OOB in this 2 bedroom condo.
Unique oceanfront home with a deck, tons of natural light, & amazing views
8.6 out of 10, Excellent, (49)
"Beautiful property. Saw seals from living room catching fish. Front door did not lock but it’s a safe neighborhood but a bit isolated. Kitchen is well equipped for cooking. Laundry facilities were a great help! Gorgeous views of the water and excellent service and communication."
Unique oceanfront home with a deck, tons of natural light, & amazing views
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator
9.8 out of 10, Exceptional, (185)
"We wanted a quiet get-a-way after raising 5 children. This was perfect, quiet after Labor Day, beautiful weather, sunrises, and week of the full moon. No obstruction for the sunrises other that a couple days of fog, same with the full moon rises. Unit was clean, nicely furnished with furniture and kitchen items. "
The price is AU$504
includes taxes & fees
8 Oct - 9 Oct
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator
East Grand Ave Fabulous Cottage
9.2 out of 10, Wonderful, (128)
"Close to everything "
East Grand Ave Fabulous Cottage
Elegant condo - walk to Portland's best restaurants & Old Port
9.4 out of 10, Exceptional, (53)
"Cute little spot near oxbow. Short drive to downtown. Great kitchen if you cook. Neighborhood seems Soso during the day and strangely decent at night. Pretty ideal. Best deal the weekend we stayed even over all the hotels. Worked out great. "
The price is AU$618
includes taxes & fees
29 Sept - 30 Sept
Elegant condo - walk to Portland's best restaurants & Old Port
Amazing beachside condo w/private balcony/free WiFi/full kitchen - near Portland
8.2 out of 10, Very good, (36)
"Enjoyed our visit. Thanks"
Amazing beachside condo w/private balcony/free WiFi/full kitchen - near Portland
Rent a room in the gorgeous Holt House
8.2 out of 10, Very good, (22)
"We loved staying at the Holt House. It's a truly beautiful building. It's like staying in a hotel from another era. The room was beautifully decorated with victorian decor and we loved it. It was also handy to have access to a full kitchen on the first floor where we washed some of our dishes. Overall, it was a cozy and quiet place to stay."
Rent a room in the gorgeous Holt House
Laurel Shore Cottage with Seasonal Private Tidal Dock, Pet friendly.
9.6 out of 10, Exceptional, (34)
"Perfect rental for me and my dog. Lots of windows and light, with gorgeous views right on the water. The deck is fantastic. Great location - very quiet (except the gulls and an occasional owl), but also convenient to restaurants and such. Kitchen had everything I needed and furniture was all lovely and comfy. "
Laurel Shore Cottage with Seasonal Private Tidal Dock, Pet friendly.
Fun Family House w/Free WiFi and Furnished Patio - Short Walk to the Beach
7.4 out of 10, Good, (10)
"House was clean. The trash in the yard was over turned and spilling everywhere when we got there and there was a ton of it but it was picked up within 2 hours of us being there. Comfy house, cute. We couldn’t use the back deck there are holes in the deck covered by carpets. Great location overall we had a great family vacation with two families."
Fun Family House w/Free WiFi and Furnished Patio - Short Walk to the Beach
Adorable Portland getaway on the Eastern Promenade
9.8 out of 10, Exceptional, (80)
"The apartment felt like home from the moment we arrived. The location was fantastic, everything we wanted to do was about 5 minutes away. The stairs up to the 3rd floor are narrow, but structurally sound. We had a great time and would recommend this location to anyone wanting to visit Portland Maine!"
The price is AU$424
includes taxes & fees
20 Oct - 21 Oct
Adorable Portland getaway on the Eastern Promenade
Glorious getaway on Portland's Eastern Promenade.
10.0 out of 10, Exceptional, (136)
"Cute house, apartment is the whole first floor. We enjoyed our stay, near downtown and the eastern promenade. Would recommend."
Glorious getaway on Portland's Eastern Promenade.
Sensational House on Sebago Lake, Raymond, ME
9.6 out of 10, Exceptional, (43)
"We had a wonderful time. Great location, house was great, plenty of kayaks and paddle boards. Great outside spaces. Our one minor complaint would be the sectional sofa on the main floor - well worn so it sinks down and is not very comfortable and hard to get out of for us older folks! Beds very comfortable, beautiful bathrooms, very clean."
Sensational House on Sebago Lake, Raymond, ME
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Other types of properties in Casco Bay Islands you may be interested in

Casco Bay Hotel, Ascend Hotel Collection
3.5 star property
8.4 out of 10, Very good, (2143)
"Grateful for staff at my very late check in at 23:30. Kind and friendly. Comfortable bed. Safe. Close to mall. Short drive to Portland. Lots of parking. Clean bathroom. Fridge in room. Continental breakfast."
The price is AU$125
includes taxes & fees
20 Oct - 21 Oct
Casco Bay Hotel, Ascend Hotel Collection
Ramada Plaza by Wyndham Portland
3.0 star property
7.6 out of 10, Good, (1022)
"Enjoyed my stay here. Staff is very helpful and friendly. The location is very convenient. "
The price is AU$158
includes taxes & fees
27 Oct - 28 Oct
Ramada Plaza by Wyndham Portland
Portland Harbor Hotel
4.0 star property
9.2 out of 10, Wonderful, (1352)
"Very comfortable and large rooms. Staff were all very friendly Location - in the centre of the old town of Portland is perfect as is access to the wonderful restaurants nearby."
The price is AU$417
includes taxes & fees
27 Oct - 28 Oct
Portland Harbor Hotel
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.