Cliff Island Holiday Rentals from €135: Search Short-Term Rentals

Q: What are some of the best holiday rentals that Cliff Island has to offer?

The Perfect Beach Escape: Cozy 4-Bedroom Retreat : This holiday home rental outside of Cliff Island is located on the beach, and has a fireplace, a balcony and a BBQ 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 that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Cliff Island holiday 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

includes taxes & fees

3 Nov - 4 Nov

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

2. Evalina Hotel

Downtown Portland

Rick

includes taxes & fees

10 Nov - 11 Nov

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

includes taxes & fees

9 Nov - 10 Nov

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

includes taxes & fees

26 Oct - 27 Oct

5. Glorious getaway on Portland's Eastern Promenade.

Munjoy Hill

William

includes taxes & fees

22 Oct - 23 Oct

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.

includes taxes & fees

1 Nov - 2 Nov

A wooden deck with outdoor seating and string lights.

7. Full sized home

Harpswell

Erika T.

includes taxes & fees

4 Nov - 5 Nov

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.

includes taxes & fees

22 Oct - 23 Oct

9. Ocean View East End Studio in a Historic Victorian

Portland

Bryan F.

includes taxes & fees

25 Oct - 26 Oct

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.

includes taxes & fees

3 Nov - 4 Nov

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.

includes taxes & fees

27 Oct - 28 Oct

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

12. Willard Beach–Apartment Near Portland & Parks

Willard Beach

Linda

includes taxes & fees

25 Oct - 26 Oct

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.

includes taxes & fees

26 Oct - 27 Oct

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.

includes taxes & fees

17 Nov - 18 Nov

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.

includes taxes & fees

25 Oct - 26 Oct

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.

includes taxes & fees

21 Nov - 22 Nov

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.

A residential area with houses, a clear blue sky, and a lake in the background.

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

Munjoy Hill

Janet S.

includes taxes & fees

19 Nov - 20 Nov

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.

includes taxes & fees

25 Oct - 26 Oct

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.

includes taxes & fees

28 Oct - 29 Oct

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Top Cliff Island Hotel Reviews

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."

Clarion Pointe South Portland

10/10 Excellent

"Overall, I had a wonderful stay at this hotel! The breakfast was excellent, and the bed was incredibly comfortable — honestly, it was the most comfortable hotel bed I have ever slept in! The room was spacious, with plenty of room to relax and feel comfortable. The location was also very convenient, with cafés, gas stations, and other essential places nearby. Everything we needed was easily accessible. The only area that could use some improvement is housekeeping. The floor was not very clean, and there were a couple of hairs in the bathroom. Paying a little more attention to these details would make the experience even better. Despite this minor issue, I really enjoyed my stay. The hotel itself was great, and the comfortable bed, excellent breakfast, and convenient location made up for a lot. I would absolutely stay here 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 holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Cliff Island holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Cliff Island holiday 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Cliff Island holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Cliff Island holiday rentals we have selected for you start as low as €135 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Cliff Island rentals

At Expedia, we put the best Cliff Island holiday 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 holiday.

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 holiday rentals in Cliff Island?

Yes, there are holiday rentals close to the most popular sights in Cliff Island, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Cliff Island has to offer?

The Perfect Beach Escape: Cozy 4-Bedroom Retreat: This holiday home rental outside of Cliff Island is located on the beach, and has a fireplace, a balcony and a BBQ 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 that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as 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 wider area, you’ll find Sand Beach and Casco Bay.

What are holiday rentals like in Cliff Island?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Cliff Island. Holiday rentals provide amenities such as patios, hot tubs and fire pits to help you enjoy your stay. If you're concerned about cleanliness, a holiday rental can offer a sense of security away from public hotel lifts and busy lobbies while still allowing you to travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive option for small groups.

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Cliff Island holiday 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 holiday rentals that suit your style

Top Cliff Island Hotel Reviews

Fireside Inn & Suites Portland

Spark by Hilton Portland Airport Maine Mall

Clarion Pointe South Portland

Clarion Hotel Portland Airport ME

Inn at St John Portland In-Town

Ramada Plaza by Wyndham 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

Go further with the Expedia app

Holiday Rentals in Cliff Island

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Cliff Island holiday 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 holiday rentals that suit your style

Top Cliff Island Hotel Reviews

Fireside Inn & Suites Portland

Find out more about Cliff Island

Frequently asked questions

Go further with the Expedia app