Cliff Island Holiday Rentals from NZ$259: 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

2 Nov - 3 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 spacious living area with a wooden floor, a white sofa, and a dining table with chairs. There is a kitchen area with a metal cabinet and a hanging light fixture.

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

17 Nov - 18 Nov

A corner room with large windows offering a city view.

4. Adorable Portland getaway on the Eastern Promenade

Munjoy Hill

Kiernan

includes taxes & fees

26 Oct - 27 Oct

A neatly made bed with white linens and pillows, a bedside lamp, and a framed artwork on the wall.

5. Glorious getaway on Portland's Eastern Promenade.

Munjoy Hill

William

includes taxes & fees

28 Oct - 29 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

27 Oct - 28 Oct

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

2 Nov - 3 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 residential building with a grey exterior, a visible staircase leading to the entrance, and a paved walkway with a stone border.

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

22 Oct - 23 Oct

17. Spacious 3 BR in Portland's Libbytown!

Portland

Brittney C.

includes taxes & fees

25 Oct - 26 Oct

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.

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.

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Top Cliff Island Hotel Reviews

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."

Hampton Inn Portland Downtown - Waterfront

8/10 Good

"First, the positives: location is perfect for a Portland visit. Easy walking distance to downtown and the harbor. Not far from the interstate. The staff was courteous and helpful when asked, and the property was clean and felt almost new. The negatives: for nearly mid-four figures a night there need to be more amenities. The in-room coffee was Motel 6 grade, and the breakfast as well. On our last morning, for whatever reason, the breakfast buffet, already rather skimpy, was missing many key items — no yogurt, no fresh fruit — and this not even midway through the service. As far as housekeeping goes, we stayed three nights, were away from the room most of each day, but our room was never made up. We did finally ask for some fresh towels and a resupply of tissues, and we are low-impact guests who really don’t need our bed made every day, but I was surprised that there wasn’t even an effort, or at least advance notice that we’d have to ask for housekeeping despite seeing them active in our corridors each day as we departed. I sensed that either the property was having trouble filling staff positions, or maybe they were being squeezed by their corporate overlords. In sum, for that much money I expected a little more, some extra touches that would elevate the experience beyond the basics."

Find out more about Cliff Island

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Cliff Island holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Cliff Island. 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 Cliff Island. 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 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 holiday 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 Cliff Island short-term rentals, that won’t be hard to do.

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.

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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

Clarion Pointe South Portland

Clarion Hotel Portland Airport ME

Inn at St John Portland In-Town

Spark by Hilton Portland Airport Maine Mall

Ramada Plaza by Wyndham Portland

Holiday Inn Portland-By the Bay by IHG

Portland Harbor Hotel

Tru by Hilton Portland Airport Area

Hampton Inn Portland Downtown - Waterfront

Find out more about Cliff Island

Frequently asked questions

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