Cliff Island Vacation Rentals

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Our top choices for Cliff Island vacation rentals

HomeAwhile

HomeAwhile
4.0 star property
Scarborough
9.2 out of 10, Wonderful, (30 reviews)
"It was a perfect stay!"
United States
Armando
The price is CA $149
CA $162 total
includes taxes & fees
May 10 - May 11
HomeAwhile

Centerview cottage

Centerview cottage
Harpswell
9.6 out of 10, Exceptional, (59 reviews)
"Great spot to relax and enjoy the beautiful outdoors. Very quiet and amazing views of the water. Everything needed for a comfortable and relaxing getaway. Highly recommend if coming to the area! "
United States
Erin
The price is CA $401
CA $648 total
includes taxes & fees
May 2 - May 3
Centerview cottage

Evalina Hotel

Evalina Hotel
2.5 star property
Downtown Portland
The price is CA $270
CA $498 total
includes taxes & fees
May 10 - May 11
Evalina Hotel

Camp Forever cottage

Camp Forever cottage
Harpswell
9.6 out of 10, Exceptional, (58 reviews)
"Everything was great, fantastic location!"
United States
Dennis H.
The price is CA $257
CA $462 total
includes taxes & fees
May 2 - May 3
Camp Forever cottage

Fred Cottage - Spacious retreat on Popham Beach!

Fred Cottage - Spacious retreat on Popham Beach!
Phippsburg
9.6 out of 10, Exceptional, (4 reviews)
"Off the beaten path, easy access to beach and Spinneys"
United States
Sean B.
Fred Cottage - Spacious retreat on Popham Beach!

Modern Getaway by the Sea

Modern Getaway by the Sea
South Portland
10.0 out of 10, Exceptional, (3 reviews)
"Enjoyed our girls weekend catching up and relaxing in this lovely space, with plenty of room and everything we needed! Host was very responsive. Would definitely stay again!"
United States
Kelley F.
The price is CA $441
CA $734 total
includes taxes & fees
May 3 - May 4
Modern Getaway by the Sea

Spectacular waterfront home with panoramic views on 4 private acres !

Spectacular waterfront home with panoramic views on 4 private acres !
Harpswell
10.0 out of 10, Exceptional, (81 reviews)
"Beautiful location, house, accommodations and views. Would recommend this location and owners highly."
United States
jeanette r.
Spectacular waterfront home with panoramic views on 4 private acres !

Modern, Luxurious Cabin in the Woods - 03

Modern, Luxurious Cabin in the Woods - 03
Freeport
10.0 out of 10, Exceptional, (6 reviews)
"This was a perfect little cabin. It was clean, well equipped with a nice kitchen and bathroom, quiet and wooded location, and comfy bed. "
United States
Chris B.
The price is CA $266
CA $453 total
includes taxes & fees
May 3 - May 4
Modern, Luxurious Cabin in the Woods - 03

Pine Point Beach private, quaint, charming studio.

Pine Point Beach private, quaint, charming studio.
Blue Point
10.0 out of 10, Exceptional, (29 reviews)
"A great location to see Portland and surroundings. A very clean and nice place to stay. "
United States
Pam B.
The price is CA $196
CA $377 total
includes taxes & fees
May 3 - May 4
Pine Point Beach private, quaint, charming studio.

Vacation Creation Downtown Brunswick 2King Beds

Vacation Creation Downtown Brunswick 2King Beds
Brunswick
9.6 out of 10, Exceptional, (19 reviews)
"Stayed here while visiting Bowdoin. Great place!"
United States
Deborah B.
The price is CA $211
CA $539 total
includes taxes & fees
May 3 - May 4
Vacation Creation Downtown Brunswick 2King Beds

2 bedroom w/ expansive water views

2 bedroom w/ expansive water views
West Point
10.0 out of 10, Exceptional, (3 reviews)
"Place was clean, beautiful and the photos do not do it justice. The perfect get away vacation from the rat race."
United States
Gregory M.
The price is CA $171
CA $330 total
includes taxes & fees
May 3 - May 4
2 bedroom w/ expansive water views

Fantastic Waterfront Views

Fantastic Waterfront Views
West Point
9.8 out of 10, Exceptional, (16 reviews)
"The location and views were incredible. Quiet and relaxing spot."
United States
Vanessa W.
The price is CA $214
CA $403 total
includes taxes & fees
May 3 - May 4
Fantastic Waterfront Views

Large, luxurious geodesic dome - 04

Large, luxurious geodesic dome - 04
Freeport
10.0 out of 10, Exceptional, (2 reviews)
"We didn’t get enough time to evaluate but from the short visit, we can say that this is the small paradise within the Main area. Best camp ground facilities we have ever seen or experienced. Looking forward to visit with friends and extended families as well. "
United States
Hrishi K.
The price is CA $330
CA $549 total
includes taxes & fees
May 10 - May 11
Large, luxurious geodesic dome - 04

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, (73 reviews)
"Had a really nice stay. "
United States
John F.
The price is CA $1,139
CA $1,674 total
includes taxes & fees
May 4 - May 5
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

Mid Coast Getaway w/ water views

Mid Coast Getaway w/ water views
West Point
9.2 out of 10, Wonderful, (5 reviews)
"Second time we have stay in this cottage. The perfect location for a Maine vacation. "
United States
chuck c.
The price is CA $143
CA $293 total
includes taxes & fees
May 3 - May 4
Mid Coast Getaway w/ water views

Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach

Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach
Brunswick
10.0 out of 10, Exceptional, (148 reviews)
"Lovely space, comfortable bed, very convenient to downtown Brunswick."
United States
Kimberly G.
The price is CA $122
CA $163 total
includes taxes & fees
May 25 - May 26
Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach

Glorious getaway on Portland's Eastern Promenade.

Glorious getaway on Portland's Eastern Promenade.
Munjoy Hill
9.8 out of 10, Exceptional, (174 reviews)
"Very cute and comfy. We would definitely stay here again. "
United States
Marie s.
The price is CA $240
CA $435 total
includes taxes & fees
May 4 - May 5
Glorious getaway on Portland's Eastern Promenade.

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, (68 reviews)
"Place was great and fenced in backyard for our dog. "
United States
Billy N.
The price is CA $171
CA $339 total
includes taxes & fees
May 3 - May 4
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach

Harborview - Curated East End Escape w/ Parking

Harborview - Curated East End Escape w/ Parking
Munjoy Hill
10.0 out of 10, Exceptional, (9 reviews)
"What a wonderful weekend in Portland Maine. The property was exceptional and in a great area. We felt comfortable and safe for our stay. We had a great time!"
United States
Kristyn E.
The price is CA $471
CA $804 total
includes taxes & fees
May 3 - May 4
Harborview - Curated East End Escape w/ Parking

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, (40 reviews)
"Great home, great location, very accommodating, clear communication."
United States
Kristi H.
The price is CA $367
CA $642 total
includes taxes & fees
May 7 - May 8
Modern & Sunny House Steps from the Promenade. Private Parking!
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Cliff Island. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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?

Steps from Old Port. New, Beautifully Appointed Home. Sleeps up to 11.: This vacation home rental outside of Cliff Island is located in the city center and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

What can I see and do in Cliff Island?

Explore the area and family-friendly sights such as Portland Observatory, 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.