Cliff Island Vacation Rentals

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Check prices for these dates

In two weeks
Dec 19 - Dec 21
In two months
Jan 30 - Feb 1
In three months
Feb 27 - Mar 1
In four months
Mar 27 - Mar 29

Vacation Rentals in Cliff Island

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, (88)
"Loved this place and would definitely stay here next time we go back."
United States
Eleni
The price is ￥28,612
￥42,818 total
includes taxes & fees
Jan 5 - Jan 6, 2026
The Weldon Hotel
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)
"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!
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)
"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.
The price is ￥108,436
￥212,379 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Perfect for Families & friends re-unions! Outdoor Hot Tub, 50 yards to the beach!
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, (234)
"Tremendous stay, great property and host."
United States
Curtis G.
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach
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)
"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.
The price is ￥133,257
￥243,154 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Sensational Beachfront Property Old Orchard Beach, with indoor elevator
1 bedroom, bed sheets
Studio Unit Walkable Everywhere

Studio Unit Walkable Everywhere

West Bayside
5.8 out of 10, (7)
"We didn't stay there at all. Canceled reservation "
United States
Dianne
The price is ￥10,588
￥21,726 total
includes taxes & fees
Dec 7 - Dec 8
Studio Unit Walkable Everywhere
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, (17)
"Incredibly wonderful beach house. Plenty of room for 8 adults, 6 children. Would recommend for any group with lots of ages and preferences. Helped to create wonderful family reunion."
United States
Ina-Lee B.
Spacious 7-bedroom house with WiFi and AC in fabulous Pine Point Scarborough
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
Fridge, microwave, oven, stovetop
Private Entrance Residential Portland

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
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, (65)
"Place was great and fenced in backyard for our dog. "
United States
Billy N.
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach
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
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

East Deering
10.0 out of 10, Exceptional, (66)
"Nice stay. Good amenities. "
United States
Laura H.
The price is ￥108,203
￥166,640 total
includes taxes & fees
Dec 7 - Dec 8
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
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, (227)
"The view off the deck was breathtaking "
United States
Raymond
The price is ￥27,139
￥52,571 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator
Fridge, microwave, oven, stovetop
1 room luxury ocean front studio cottage

1 room luxury ocean front studio cottage

Harpswell
9.6 out of 10, Exceptional, (171)
"Very clean beautiful view we definitely enjoyed ourselves "
United States
Ilona F.
1 room luxury ocean front studio cottage
Outdoor dining
Spectacular Beachfront Condo-Watch sunrise from deck overlooking beach.

Spectacular Beachfront Condo-Watch sunrise from deck overlooking beach.

Old Orchard Beach
9.8 out of 10, Exceptional, (36)
"Great spot...everything was great "
United States
Frank R.
Spectacular Beachfront Condo-Watch sunrise from deck overlooking beach.
Property grounds
Charming 2-bedroom house with AC, WiFi in lovely Falmouth

Charming 2-bedroom house with AC, WiFi in lovely Falmouth

Falmouth
8.8 out of 10, Excellent, (6)
"We had a wonderful stay. Nice comfortable camp. We enjoyed swimming in the lake. "
United States
Darcie B.
Charming 2-bedroom house with AC, WiFi in lovely Falmouth
TV
In-town no frills 2 bedroom apt

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.
The price is ￥13,031
￥24,169 total
includes taxes & fees
Dec 7 - Dec 8
In-town no frills 2 bedroom apt
Exterior
Beautiful Oceanfront House- Stunning Water Views

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
Property grounds
Little Miss Cottages

Little Miss Cottages

2.5 star property
Surfside
8.4 out of 10, Very Good, (88)
"Cute and tidy cottage, easy walk to beautiful beach."
United States
Charlotte
Little Miss Cottages
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)
"Perfect location by the beach and great communication with the owner! "
Canada
Marie-Christine B.
Best house in Old Orchard Beach..STEPS/BEACH, surf!!!! 4 bedroom
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 Cliff Island Hotel Reviews

DoubleTree by Hilton Hotel Portland

DoubleTree by Hilton Hotel Portland

10/10 Excellent
"Nice staff. Yummy cookie. Clean room. Comfy bed. Lobby coffee. "
Melissa 1-night trip
Posted 2 days ago
DoubleTree by Hilton Hotel Portland

Find out more about Cliff Island

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

Frequently asked questions

Can I find vacation rentals in Cliff Island?

Yes, there are vacation rentals close to top sights in Cliff Island, or you can choose a more remote option if you want a relaxing place to stay.

What are some of the best vacation home rentals in Cliff Island?

Perfect for Families & friends re-unions! Outdoor Hot Tub, 50 yards to the beach!: This vacation home rental outside of Cliff Island is located near the beach and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, an arcade game room, and a hot tub so you can immerse yourself in your vacation.

What can I see and do in Cliff Island?

Explore the area and family-friendly sights such as Maine Narrow Gauge Railroad Company and Museum, or get out into nature at a spot like Sand Beach. In the larger area, you’ll find Fifth Maine Museum and Casco Bay.

What are vacation rentals like in Cliff Island?

Vacation rentals are privately owned properties you can reserve for a few days or a quick weekend in Cliff Island. Vacation rentals offer extras like WiFi and washers and dryers so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, a vacation rental can provide a sense of safety away from public hotel elevators and busy front desks while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great option for a family trip.