Cliff Island Vacation Rentals from $128: Search Short-Term Rentals

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

The Perfect Beach Escape: Cozy 4-Bedroom Retreat : This vacation home rental outside of Cliff Island is located on the beach and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 4 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.

Check prices for these dates

In two weeks

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Our top choices for Cliff Island vacation rentals

A modern kitchen with a central island, bar stools, a dining table, and a built-in oven.

1. The Weldon Hotel

Downtown Portland

Victoria

$284 nightly

Nov 17 - Nov 18

Total with taxes and fees

A multi-story building with a stone facade, large windows, and a corner entrance.

2. Evalina Hotel

Downtown Portland

Rick

$402 nightly

Nov 17 - Nov 18

Total with taxes and fees

A beach with a wooden chair and a small building in the background.

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

Willard Beach

"Property manager was very kind but a little hard to get a hold of. Owner of the property was amazing and in contact immediately. The house is quaint, cute and perfect for a beautiful stay on the coast. We enjoyed the location more than anything. The owners left a binder with a lot of very helpful information for restaurants, stores, etc. If you want to stay in the area, you can walk almost anywhere. All in all we loved our stay and would return."

James

$440 nightly

Nov 18 - Nov 19

Total with taxes and fees

A street lined with buildings, one with a red door and a sign that reads "MINATO".

4. Adorable Portland getaway on the Eastern Promenade

Munjoy Hill

Kiernan

$265 nightly

Oct 26 - Oct 27

Total with taxes and fees

5. Glorious getaway on Portland's Eastern Promenade.

Munjoy Hill

William

$408 nightly

Oct 26 - Oct 27

Total with taxes and fees

A kitchen with a wooden countertop, a black kettle, a vase with flowers, and a small wire basket.

6. Charming Studio Retreat with Queen bed, WiFi, and AC in welcoming Portland

Munjoy Hill

Aimee S.

$212 nightly

Nov 1 - Nov 2

Total with taxes and fees

A wooden deck with outdoor seating and string lights.

7. Full sized home

Harpswell

Erika T.

$339 nightly

Oct 27 - Oct 28

Total with taxes and fees

A living room with a sofa, armchair, and glass coffee table. There are two lamps on side tables and a window with curtains.

8. Portland 1-bedroom with enclosed porch & parking

Deering Center

Cricket C.

$109 nightly

Oct 27 - Oct 28

Total with taxes and fees

9. Ocean View East End Studio in a Historic Victorian

Portland

Bryan F.

$423 nightly

Oct 25 - Oct 26

Total with taxes and fees

A modern kitchen with a central island, stainless steel appliances, and contemporary artwork.

10. A Peaceful Oasis on Munjoy Hill: 1st flr - 3BR + parking

Munjoy Hill

Benton M.

$355 nightly

Nov 2 - Nov 3

Total with taxes and fees

A grassy area with a picnic table and chairs, a body of water, and two trees in the background.

11. Orchid Harbor, Bailey Island 3BR

Harpswell

Jane D.

$391 nightly

Oct 27 - Oct 28

Total with taxes and fees

A dining table with chairs, a potted plant, and decorative items.

12. Willard Beach–Apartment Near Portland & Parks

Willard Beach

Linda

$268 nightly

Oct 25 - Oct 26

Total with taxes and fees

A house with a wooden front door, a stone staircase, and a porch with a wooden railing.

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

East Deering

Mike G.

$1,020 nightly

Oct 26 - Oct 27

Total with taxes and fees

A coastal view with a house, a tree, and a beach.

14. Willard By the Sea - 30 ft to the beach- 2nd floor

Willard

"Fantastic beach location and comfortable unit equipped with air conditioning (essential during the heat wave that occurred during our stay). Clean rooms, good size and full kitchen; comfortable furnishings.Only caution is that this is a beach-side location and appears to have a bit of a price premium for that reason. It’s justified but only if you’re planning to make good use of the beach."

Gerald B.

$529 nightly

Nov 17 - Nov 18

Total with taxes and fees

A bedroom with a bed, a nightstand, a lamp, a door, and a staircase.

15. Great suburban location close to town!

Deering Center

Peter H.

$95 nightly

Oct 25 - Oct 26

Total with taxes and fees

A room with a sliding glass door leading to an outdoor deck with Adirondack chairs and a table.

16. Three bedroom in United States of America, Freeport

Freeport

"What can I say about my stay; peaceful, beautiful views, and relaxing! Home was clean with modern finishes but super comfortable for my four guests. The downstairs area is very private from the main floor. The yard was a great space where we had our outdoor fire looking up at the stars at night. The deck was perfect for our family lunch and dinners. We took chairs down to the beach area to sit closer to the water which was perfect. It's super close to town, Wolfe's Neck and other amenities....

Lisa E.

$867 nightly

Nov 8 - Nov 9

Total with taxes and fees

A building with a brick facade, large windows, and a covered outdoor seating area.

17. Spacious 3 BR in Portland's Libbytown!

Portland

Brittney C.

$395 nightly

Oct 25 - Oct 26

Total with taxes and fees

A garden with a stone wall, a small pond, and various plants.

18. 4br2ba House parking A Peaceful Oasis on Munjoy Hill

Munjoy Hill

Janet S.

$546 nightly

Nov 19 - Nov 20

Total with taxes and fees

A spacious living room with large windows, a sofa, a coffee table, and a view of the city.

19. Spectacular Views & Comforts of Home in Portland s Most Desirable Neighborhood

Munjoy Hill

Patricia S.

$504 nightly

Oct 25 - Oct 26

Total with taxes and fees

A kitchen with a wooden island, black bar stools, a hanging light fixture, and a framed botanical print on the wall.

20. Spacious 4-bedroom house located in the heart of Portland, ME.

Munjoy Hill

Matt H.

$834 nightly

Oct 28 - Oct 29

Total with taxes and fees

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Top Cliff Island Hotel Reviews

Clarion Hotel Portland Airport ME

10/10 Excellent

"A nice hotel in a good location. My room was spacious, clean and quiet. The staff are really great. They answer all your questions and try to help you as much as possible. They also have free shuttle service to wherever you want to go all over the city. They drop of you off and pick you up. You can't beat that."

The Westin Portland Harborview

10/10 Excellent

"Stayed in a King bed Studio-type room. It was clean upon arrival, checked in easily at the front desk, received 2 breakfast tickets (paid an extra fee on Expedia), and was given complementary apps at their C2 restaurant (non-alcoholic beverages) since we were celebrating our anniversary. There were various breakfast options to choose from at C2 restaurant, and staff were so friendly and helpful. We also checked out Top of the East; their lounge and bar at the top floor. They had a live DJ on Saturday evening."

Grand Beach Inn

8/10 Good

"Nothing is better than an old motel directly across from the ocean. Off season staff hours appear to be nonexistent as my key was waiting in a mailbox. Getting a third floor corner room with no elevator nor view was a kick in butt. 6 or so corner rooms are situated in the corners where there isn't a view nor a balcony. Judging by the 10 or so cars in the lot, a lower level room or view was likely available."

Fireside Inn & Suites Portland

10/10 Excellent

"The staff is always very welcoming and pleasant. We had a small issue with our room (floor was wet near the ac unit) but staff on duty had us moved into an upgraded, newer room that was quite nice and had done so within a few minutes. Overall great place and we will visit again."

Portland Harbor Hotel

10/10 Excellent

"Excellent, well-situated hotel. Front desk personnel were helpful and courteous. Sean and Simone were so kind in finding us the perfect room to suit our needs. Olivia at the bar in the evening was professional; we enjoyed our conversations with her. Great coffee-nook with perfect additions for a continental breakfast. Thanks to all who helped make our stay so enjoyable."

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 $128 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?

The Perfect Beach Escape: Cozy 4-Bedroom Retreat: This vacation home rental outside of Cliff Island is located on the beach and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 4 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 Maine Narrow Gauge Railroad, or get out into nature at a spot like Little John Island Preserve. In the larger area, you’ll find Sand Beach 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.

Room 1

Check prices for these dates

Our top choices for Cliff Island vacation rentals

1. The Weldon Hotel

2. Evalina Hotel

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

4. Adorable Portland getaway on the Eastern Promenade

5. Glorious getaway on Portland's Eastern Promenade.

6. Charming Studio Retreat with Queen bed, WiFi, and AC in welcoming Portland

7. Full sized home

8. Portland 1-bedroom with enclosed porch & parking

9. Ocean View East End Studio in a Historic Victorian

10. A Peaceful Oasis on Munjoy Hill: 1st flr - 3BR + parking

11. Orchid Harbor, Bailey Island 3BR

12. Willard Beach–Apartment Near Portland & Parks

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

14. Willard By the Sea - 30 ft to the beach- 2nd floor

15. Great suburban location close to town!

16. Three bedroom in United States of America, Freeport

17. Spacious 3 BR in Portland's Libbytown!

18. 4br2ba House parking A Peaceful Oasis on Munjoy Hill

19. Spectacular Views & Comforts of Home in Portland s Most Desirable Neighborhood

20. Spacious 4-bedroom house located in the heart of Portland, ME.

Find vacation rentals that suit your style

Top Cliff Island Hotel Reviews

Clarion Hotel Portland Airport ME

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

Spark by Hilton Portland Airport Maine Mall

The Westin Portland Harborview

Grand Beach Inn

Fireside Inn & Suites Portland

Holiday Inn Portland-By the Bay by IHG

Portland Harbor Hotel

Tru by Hilton Portland Airport Area

Find out more about Cliff Island

Frequently asked questions