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Cliff Island Vacation Rentals

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Our top choices for Cliff Island vacation rentals

City Amenities, Casco Bay Sunrises and Natural Beauty

City Amenities, Casco Bay Sunrises and Natural Beauty
East Deering
9.8 out of 10, Exceptional, (130 reviews)
"Wonderful place! Owner very responsible! Would stay again! Great choice for place to stay away from home."
United States
Arlene L.
$436 nightly
The price is $475
Aug 3 - Aug 4
Total with taxes and fees
City Amenities, Casco Bay Sunrises and Natural Beauty

Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (54 reviews)
"Wonderful stay!"
United States
Erika T.
$336 nightly
The price is $366
Jul 21 - Jul 22
Total with taxes and fees
Full sized home

Fortland Island Campground

Fortland Island Campground
1.0 star property
Portland
10.0 out of 10, Exceptional, (3 reviews)
"It was very quiet and liked the experience of staying in a camp like setting."
United States
leela srinivas
$249 nightly
The price is $272
Jul 21 - Jul 22
Total with taxes and fees
Fortland Island Campground

Evalina Hotel

Evalina Hotel
2.5 star property
Downtown Portland
10.0 out of 10, Exceptional, (5 reviews)
"Spacious, clean, and in the perfect location in Old Port."
United States
Celine
$771 nightly
The price is $841
Jul 27 - Jul 28
Total with taxes and fees
Evalina Hotel

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, (76 reviews)
"This is such a great house and it was perfect for our group! We would definitely stay there again "
United States
Catherine T.
$1,758 nightly
The price is $1,916
Aug 7 - Aug 8
Total with taxes and fees
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

Arlie`s Digs! - One Block To Willard Beach!

Arlie`s Digs! - One Block To Willard Beach!
Willard Beach
10.0 out of 10, Exceptional, (66 reviews)
"Beautiful place, perfect location! "
United States
Melissa M.
$672 nightly
The price is $733
Jul 23 - Jul 24
Total with taxes and fees
Arlie`s Digs! - One Block To Willard Beach!

The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (102 reviews)
"Spacious with plenty of room for my family of four. Excellent kitchen, washer and dryer and stellar location close to Waterfront district."
United States
Kara
$518 nightly
The price is $558
Jul 28 - Jul 29
Total with taxes and fees
The Weldon Hotel

Peaceful & minutes from the Old Port with private parking

Peaceful & minutes from the Old Port with private parking
Knightville
9.6 out of 10, Exceptional, (10 reviews)
"Jennifer’s VRBO is exactly as cute, clean and cozy as the listing’s photos depict. It is so well maintained that she has living house plants that are thriving 10/10. I can’t wait to stay again!"
United States
Liz P.
$351 nightly
The price is $383
Jul 21 - Jul 22
Total with taxes and fees
Peaceful & minutes from the Old Port with private parking

Portland’s Best Ocean Views from a 40-Foot Private Deck

Portland’s Best Ocean Views from a 40-Foot Private Deck
Munjoy Hill
9.6 out of 10, Exceptional, (26 reviews)
"Beautiful location with easy walk to downtown. "
United States
Megan T.
$771 nightly
The price is $840
Jul 21 - Jul 22
Total with taxes and fees
Portland’s Best Ocean Views from a 40-Foot Private Deck

Ocean View East End Studio in a Historic Victorian

Ocean View East End Studio in a Historic Victorian
Portland
9.8 out of 10, Exceptional, (104 reviews)
"Lovely view and accessibility to the Old Port area. Enjoyed our relaxing stay! Thanks Dan! "
United States
David E.
$423 nightly
The price is $461
Aug 2 - Aug 3
Total with taxes and fees
Ocean View East End Studio in a Historic Victorian

Modern & Sunny House Steps from the Promenade. Private Parking!

Modern & Sunny House Steps from the Promenade. Private Parking!
Munjoy Hill
10.0 out of 10, Exceptional, (42 reviews)
"Perfect stay for a quick trip to Portland! "
United States
stacey p.
$697 nightly
The price is $760
Jul 26 - Jul 27
Total with taxes and fees
Modern & Sunny House Steps from the Promenade. Private Parking!

Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants

Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants
Munjoy Hill
9.8 out of 10, Exceptional, (132 reviews)
"Home is in an excellent location, and as described. Easy communication with zero issues during stay. Great experience overall and will return! "
United States
Christina A.
$646 nightly
The price is $704
Jul 22 - Jul 23
Total with taxes and fees
Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants

Sunny Spot with Private Parking.

Sunny Spot with Private Parking.
Knightville
9.8 out of 10, Exceptional, (30 reviews)
"Cute property.. also really suitable for long stay as the amenities were complete and near groceries and some restaurants and cafes.. convenient!"
United States
Giana
$349 nightly
The price is $380
Jul 26 - Jul 27
Total with taxes and fees
Sunny Spot with Private Parking.

Industrial Farmhouse Chic in Portland`s Most Desirable Neighborhood

Industrial Farmhouse Chic in Portland`s Most Desirable Neighborhood
Munjoy Hill
9.8 out of 10, Exceptional, (39 reviews)
"We were four couples who enjoyed our weekend stay. Easy walk to downtown to delicious restaurants and shopping. "
United States
Kristin M.
$856 nightly
The price is $933
Jul 21 - Jul 22
Total with taxes and fees
Industrial Farmhouse Chic in Portland`s Most Desirable Neighborhood

Vintage Maine & Modern Convenience in Portlands Exclusive East End

Vintage Maine & Modern Convenience in Portlands Exclusive East End
Munjoy Hill
9.8 out of 10, Exceptional, (54 reviews)
"Great location. Short walk to Old Port and shops restaurants. Host was great"
United States
Jeff P.
$553 nightly
The price is $603
Aug 13 - Aug 14
Total with taxes and fees
Vintage Maine & Modern Convenience in Portlands Exclusive East End

Harborview - Curated East End Escape w/ Parking

Harborview - Curated East End Escape w/ Parking
Munjoy Hill
10.0 out of 10, Exceptional, (12 reviews)
"It was a beautiful property with everything you could need available. There were a lot of little touches that made it really nice! "
United States
Jeannette B.
$914 nightly
The price is $996
Jul 27 - Jul 28
Total with taxes and fees
Harborview - Curated East End Escape w/ Parking

Glorious getaway on Portland's Eastern Promenade.

Glorious getaway on Portland's Eastern Promenade.
Munjoy Hill
9.8 out of 10, Exceptional, (180 reviews)
"Location was great. We walked to most places, kids love the trail and playground down the street. Parking on the street was easy. Beautiful front room with lots of natural light!"
United States
Gina F.
$466 nightly
The price is $508
Jul 28 - Jul 29
Total with taxes and fees
Glorious getaway on Portland's Eastern Promenade.

Adorable Portland getaway on the Eastern Promenade

Adorable Portland getaway on the Eastern Promenade
Munjoy Hill
9.6 out of 10, Exceptional, (138 reviews)
"Owner was so accommodating!"
United States
Kiernan
$366 nightly
The price is $399
Aug 3 - Aug 4
Total with taxes and fees
Adorable Portland getaway on the Eastern Promenade

Three bedroom in United States of America, Freeport

Three bedroom in United States of America, Freeport
Freeport
10.0 out of 10, Exceptional, (2 reviews)
"All we could say was wow! Words cannot express the view from this house! It looked like a picture! Beautiful view, fully loaded kitchen, spacious, comfortable beds, everything was perfect. I have the worst cell service and I couldn’t get the app to work but David answered my call right away and helped us get in. I’d highly recommend this property and we can’t wait to come back!"
United States
Michael L.
$1,018 nightly
The price is $1,109
Jul 28 - Jul 29
Total with taxes and fees
Three bedroom in United States of America, Freeport

The Globe House on Munjoy Hill - Walk to Breweries

The Globe House on Munjoy Hill - Walk to Breweries
Munjoy Hill
10.0 out of 10, Exceptional, (100 reviews)
"Everything was as advertised; great accommodations!"
United States
Richard D.
$638 nightly
The price is $695
Aug 18 - Aug 19
Total with taxes and fees
The Globe House on Munjoy Hill - Walk to Breweries
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

Find out more about Cliff Island

Everything you need to know about Cliff Island vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Cliff Island vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Cliff Island vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Cliff Island vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Cliff Island. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Cliff Island in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $184 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Cliff Island rentals

At Expedia, we put the best Cliff Island vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Cliff Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Cliff Island vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Cliff Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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?

New Listing. 2BR+Bonus Sleeping Room in OOB. Walk to Beach & Amusement Park.: This vacation home rental outside of Cliff Island is near the beach and equipped with air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

What can I see and do in Cliff Island?

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

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.