Cliff Island holiday rentals

We found 759 holiday rentals — enter your dates for availability
Discover a selection of holiday rentals in Cliff Island that are perfect for your trip. Whether you're going on holiday with family or friends, holiday rentals have the best amenities for hanging out with the people that matter most, including Wi-Fi and parking. At the end of the day, you're sure to find a property to rent to meet everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts – Cliff Island

Showing deals for:13 Nov - 20 Nov

Bathroom
Bright and comfortable living room in a quiet Portland neighborhood
Room
Quiet, tree-lined Deering neighborhood setting
Exceptional
(46 reviews)

Quiet 2BR/2BA Home w/ Parking • Dog-Friendly • Near Downtown Portland

Portland

8% off
AU$2,946
for 7 nights, 1 home
AU$421 per night
includes taxes & fees
Quiet 2BR/2BA Home w/ Parking • Dog-Friendly • Near Downtown Portland
Private kitchen
Terrace/patio
Room
Interior
Wonderful
(23 reviews)

Beautiful, single story ranch. Next to city park with ocean view!

Portland

8% off
AU$8,996
for 7 nights, 1 home
AU$1,285 per night
includes taxes & fees
Beautiful, single story ranch. Next to city park with ocean view!
Enjoy our peaceful, private screened in porch.
Private kitchen
Living area
Dining
Wonderful
(28 reviews)

Adorable, Bright and By the Bay!

Falmouth

16% off
AU$5,950
for 7 nights, 1 home
AU$850 per night
includes taxes & fees
Adorable, Bright and By the Bay!
View from Master Bedroom
Master Bedroom
Living area
Dining
Exceptional
(33 reviews)

Amazing Oceanfront Brand NewHome Ideal location -

Peaks Island

8% off
AU$7,706
for 7 nights, 1 home
AU$1,101 per night
includes taxes & fees
Amazing Oceanfront Brand NewHome Ideal location -
The living room leads out to a private deck with a dining table that seats 4.
Outdoor dining
Private kitchen
Interior
Exceptional
(42 reviews)

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

Portland

8% off
AU$4,037
for 7 nights, 1 home
AU$577 per night
includes taxes & fees
Modern & Sunny House Steps from the Promenade. Private Parking!
Dining area
Casco Bay
WELCOME
Kitchen
Exceptional
(100 reviews)

Beautiful Oceanfront Apartment, scenic views and water access

Yarmouth

8% off
AU$2,985
for 7 nights, 1 apartment
AU$426 per night
includes taxes & fees
Beautiful Oceanfront Apartment, scenic views and water access
Private kitchen
Interior
Dining
Interior
Exceptional
(31 reviews)

Sunny Spot with Private Parking.

South Portland

8% off
AU$2,242
for 7 nights, 1 apartment
AU$320 per night
includes taxes & fees
Sunny Spot with Private Parking.
Living area
Marina
Dining
Living area
Exceptional
(13 reviews)

Renovated Apartment in Willard Square Area of South Portland, Maine.

South Portland

16% off
AU$2,604
for 7 nights, 1 apartment
AU$372 per night
includes taxes & fees
Renovated Apartment in Willard Square Area of South Portland, Maine.
Kitchen at night with setup for a dinner party
Looking up to the house from Garrison Cove
Living Room Fireplace
View from Roof Top deck
Exceptional
(83 reviews)

Amazing Views, and Comfortable Spaces in this Well Appointed Island Home

Bailey Island

8% off
AU$8,549
for 7 nights, 1 home
AU$1,221 per night
includes taxes & fees
Amazing Views, and Comfortable Spaces in this Well Appointed Island Home
Private kitchen
Terrace/patio
View from living room
Living area
Exceptional
(183 reviews)

1 room luxury ocean front studio cottage

Harpswell

8% off
AU$2,191
for 7 nights, 1 apartment
AU$313 per night
includes taxes & fees
1 room luxury ocean front studio cottage
Private kitchen
Living area
Dining
Private kitchen
Exceptional
(133 reviews)

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

Portland

11% off
AU$3,028
for 7 nights, 1 apartment
AU$433 per night
includes taxes & fees
Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants
View from inside unit.
Lobby can be accessed from Patton Ct or Exchange St. Door code will be provided.
Everyone's favorite room in the home. Massive 8ftx6ft skylight.
Massive 100 inch smart TV
Exceptional
(6 reviews)

Exchange Street Skylight Loft

Portland

8% off
AU$3,057
for 7 nights, 1 apartment
AU$437 per night
includes taxes & fees
Exchange Street Skylight Loft
Room
Living area
Private kitchen
Off-street parking behind building dedicated to this unit only.
Exceptional
(37 reviews)

Eastbayside/Munjoy - Charming Downtown Escape

Portland

8% off
AU$2,819
for 7 nights, 1 apartment
AU$403 per night
includes taxes & fees
Eastbayside/Munjoy - Charming Downtown Escape
Front Hall
Heron's Perch on Peaks' Island
Living area
Living area
Exceptional
(39 reviews)

Large, light filled 4 bedroom house - walk to ocean and ferry

Peaks Island

8% off
AU$6,999
for 7 nights, 1 home
AU$1,000 per night
includes taxes & fees
Large, light filled 4 bedroom house - walk to ocean and ferry
Private kitchen
Outdoor dining
Interior
Dining
Exceptional
(11 reviews)

Peaceful & minutes from the Old Port with private parking

South Portland

8% off
AU$2,217
for 7 nights, 1 apartment
AU$317 per night
includes taxes & fees
Peaceful & minutes from the Old Port with private parking
Living area
Interior
Dining
Living area
Exceptional
(98 reviews)

2 Bedroom Apartment Unit In Portland's Historic West End Neighborhood

Portland

8% off
AU$2,897
for 7 nights, 1 apartment
AU$414 per night
includes taxes & fees
2 Bedroom Apartment Unit In Portland's Historic West End Neighborhood
Coffee/ Wine station
Coziest place to relax and unwind have a fire and enjoy the fall and winter
Private kitchen
Living area
Exceptional
(66 reviews)

Clean, Cozy, and Professional Waterfront Home- minutes to Portland

Falmouth

8% off
AU$6,436
for 7 nights, 1 home
AU$919 per night
includes taxes & fees
Clean, Cozy, and Professional Waterfront Home- minutes to Portland
Living area
Minato is a quick walk away.
View from the top of the Portland Observatory.
Open kitchen concept with a breakfast bar.
Exceptional
(140 reviews)

Adorable Portland getaway on the Eastern Promenade

Portland

12% off
AU$1,396
for 7 nights, 1 apartment
AU$199 per night
includes taxes & fees
Adorable Portland getaway on the Eastern Promenade
Living area
Interior
Interior
Walnut topped kitchenette counter with coffee maker.
Exceptional
(43 reviews)

Fresh East End Apartment Walkable to Downtown Portland

Portland

8% off
AU$4,332
for 7 nights, 1 apartment
AU$619 per night
includes taxes & fees
Fresh East End Apartment Walkable to Downtown Portland
Living room has queen size pull out sofa bed.
Property grounds
Kitchen recently renovated.
Open floor plan.
Wonderful
(39 reviews)

Stover's Cove Beach Coastal Retreat

Harpswell

8% off
AU$5,268
for 7 nights, 1 home
AU$753 per night
includes taxes & fees
Stover's Cove Beach Coastal Retreat
Living area
Minato! Japanese street food,  a short walk down the hill.
Baharat, across the street from rising tide.
Room
Exceptional
(183 reviews)

Glorious getaway on Portland's Eastern Promenade.

Portland

8% off
AU$2,416
for 7 nights, 1 apartment
AU$345 per night
includes taxes & fees
Glorious getaway on Portland's Eastern Promenade.
Large deck with seating for six, festive lighting and a firepit. Views and sun!
5 min car ride to Downtown/Old Port.
Large, well-stocked Kitchen w/stainless steel counter and appliances
Festive lighting at your control.
Exceptional
(131 reviews)

City Amenities, Casco Bay Sunrises and Natural Beauty

Portland

6% off
AU$3,184
for 7 nights, 1 apartment
AU$455 per night
includes taxes & fees
City Amenities, Casco Bay Sunrises and Natural Beauty
Dining
Interior
Room
Living area
Exceptional
(20 reviews)

West End's Diamond in the Rough 2-bedroom Apartment with Parking & WiFi

Portland

8% off
AU$4,554
for 7 nights, 1 apartment
AU$651 per night
includes taxes & fees
West End's Diamond in the Rough 2-bedroom Apartment with Parking & WiFi
Dining
Interior
Exterior detail
Property grounds
Exceptional
(21 reviews)

New England Charm, Portland - Parking included

Portland

8% off
AU$4,395
for 7 nights, 1 apartment
AU$628 per night
includes taxes & fees
New England Charm, Portland - Parking included
  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Choose a holiday rental for your Cliff Island getaway

Learn about the unique charm of Cliff Island with a stay in a holiday home rental. This city has something for everyone. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in and around Cliff Island

Do you want to find attractions to visit while you're in town? Venture out of your cosy holiday rental and check out everything that makes Cliff Island a one-of-a-kind holiday spot. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Happy Wheels Skate Center (11.2 mi / 18.1 km)
  • Nonesuch River Golf Club (13.8 mi / 22.2 km)
  • Land's End Gift Shop (5.5 mi / 8.9 km)
  • Ash Cove Pottery (6.1 mi / 9.9 km)
  • Gilsland Farm Audubon Center (6.7 mi / 10.8 km)
  • Riverside Municipal Golf Course (10.2 mi / 16.4 km)

Exploring the natural landscape of Cliff Island

Whether you're an outdoor enthusiast or just want to take in the scenery, Cliff Island is a great spot to appreciate mother nature. These are a few of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city centre:

  • Sand Beach (5.6 mi / 9.1 km)
  • Casco Bay (5.6 mi / 9.1 km)
  • East End Beach (6.9 mi / 11.1 km)
  • Willard Beach (7 mi / 11.2 km)
  • Eastern Promenade (7 mi / 11.2 km)
  • Winslow Memorial Park (7.4 mi / 12 km)

Transport options to and around Cliff Island

The nearest airport is in Portland, ME (PWM-Portland Intl. Jetport), located 10.7 mi (17.2 km) from the city centre. If you're unable to find a flight that fits your schedule, you could book a flight to Auburn, ME (LEW-Auburn - Lewiston Municipal), which is 26 mi (41.8 km) away.

Frequently asked questions

How much does it cost to rent a holiday home in Cliff Island?
Different factors affect how much you pay for a holiday home in Cliff Island, including the season, length of stay and type of property. But, all of our holiday homes have something in common — amazing value. Simply add your travel dates to find your home away from home.
How much does it cost to rent a beach house in Cliff Island?
Prices for beach houses in Cliff Island may vary depending on the type and size of the property and when you plan to travel. All you have to do is enter your travel dates into Stayz and the number of guests to see your home options and prices. From there you can use the filters to tailor your search by ratings, amenities and more.
How old do you have to be to rent a holiday home in Cliff Island?
Age restrictions can vary across properties on Stayz, so be sure to look at the rules of the holiday home in Cliff Island you're interested in. But usually, it's 16, 18 or 21.
How long can I rent a holiday home in Cliff Island for?
How long you can rent a holiday home in Cliff Island depends on the property. Just enter your selected travel dates to look at a list of options offering extended stays. With plenty of creature comforts such as laundries and air conditioning, as well as some offering weekly or monthly discounted prices, you're sure to get someplace just right to call your home away from home in Cliff Island.

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