Cliff Island holiday rentals

We found 765 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:1 Jan - 8 Jan

Quiet, tree-lined Deering neighborhood setting
Bright and comfortable living room in a quiet Portland neighborhood
Fully equipped kitchen with everything needed for cooking
Room
Exceptional
(51 reviews)

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

Portland

8% off
AU$3,278
for 7 nights, 1 home
AU$468 per night
includes taxes & fees
Quiet 2BR/2BA Home w/ Parking • Dog-Friendly • Near Downtown Portland
Living room has queen size pull out sofa bed.
Property grounds
Open floor plan.
Floors recently refinished.
Wonderful
(42 reviews)

Stover's Cove Beach Coastal Retreat

Harpswell

8% off
AU$5,298
for 7 nights, 1 home
AU$757 per night
includes taxes & fees
Stover's Cove Beach Coastal Retreat
Back yard
Willard Beach
Living area
Dining
Exceptional
(73 reviews)

Willard Beach Neighborhood-Close to all Southern Maine has to offer!

South Portland

8% off
AU$4,493
for 7 nights, 1 home
AU$642 per night
includes taxes & fees
Willard Beach Neighborhood-Close to all Southern Maine has to offer!
Dining area
Casco Bay
Kitchen
picnic area
Exceptional
(102 reviews)

Beautiful Oceanfront Apartment, scenic views and water access

Yarmouth

8% off
AU$2,998
for 7 nights, 1 apartment
AU$428 per night
includes taxes & fees
Beautiful Oceanfront Apartment, scenic views and water access
Living Room Fireplace
Looking up to the house from Garrison Cove
Dining Room Seating for ten, extra dining also available
Kitchen at night with setup for a dinner party
Exceptional
(86 reviews)

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

Bailey Island

8% off
AU$8,597
for 7 nights, 1 home
AU$1,228 per night
includes taxes & fees
Amazing Views, and Comfortable Spaces in this Well Appointed Island Home
Private kitchen
Terrace/patio
Living area
Room
Exceptional
(191 reviews)

1 room luxury ocean front studio cottage

Harpswell

8% off
AU$2,203
for 7 nights, 1 apartment
AU$315 per night
includes taxes & fees
1 room luxury ocean front studio cottage
Exterior
Property grounds
Interior
Interior
Exceptional
(8 reviews)

1 bedroom apartment beautiful location on pond in South Freeport

Freeport

16% off
AU$1,598
for 7 nights, 1 apartment
AU$228 per night
includes taxes & fees
1 bedroom apartment beautiful location on pond in South Freeport
Living area
Marina
Dining
Private kitchen
Exceptional
(13 reviews)

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

South Portland

16% off
AU$2,615
for 7 nights, 1 apartment
AU$374 per night
includes taxes & fees
Renovated Apartment in Willard Square Area of South Portland, Maine.
Dining
Living area
Interior
Private kitchen
Exceptional
(134 reviews)

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

Portland

15% off
AU$2,577
for 7 nights, 1 apartment
AU$368 per night
includes taxes & fees
Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants
Private kitchen
Living area
Interior
Off-street parking behind building dedicated to this unit only.
Exceptional
(43 reviews)

Eastbayside/Munjoy - Charming Downtown Escape

Portland

8% off
AU$5,249
for 7 nights, 1 apartment
AU$750 per night
includes taxes & fees
Eastbayside/Munjoy - Charming Downtown Escape
View from inside unit.
Large open concept living space with tall sloped celling and a loft.
Oven, Keurig, microwave, fridge, toaster, and dishwasher.
Everyone's favorite room in the home. Massive 8ftx6ft skylight.
Exceptional
(9 reviews)

Exchange Street Skylight Loft

Portland

8% off
AU$3,994
for 7 nights, 1 apartment
AU$571 per night
includes taxes & fees
Exchange Street Skylight Loft
Living area
Dining
Private kitchen
Outdoor dining
Exceptional
(147 reviews)

Fall In Love With Portland!

Portland

7% off
AU$2,778
for 7 nights, 1 apartment
AU$397 per night
includes taxes & fees
Fall In Love With Portland!
Dining
Interior
Living area
Exterior detail
Exceptional
(103 reviews)

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

Portland

8% off
AU$2,910
for 7 nights, 1 apartment
AU$416 per night
includes taxes & fees
2 Bedroom Apartment Unit In Portland's Historic West End Neighborhood
Private kitchen
Interior
Room
Living area
Exceptional
(13 reviews)

Peaceful & minutes from the Old Port with private parking

South Portland

8% off
AU$2,256
for 7 nights, 1 apartment
AU$322 per night
includes taxes & fees
Peaceful & minutes from the Old Port with private parking
Interior
Interior
Room
Walnut topped kitchenette counter with coffee maker.
Exceptional
(44 reviews)

Fresh East End Apartment Walkable to Downtown Portland

Portland

8% off
AU$4,312
for 7 nights, 1 apartment
AU$616 per night
includes taxes & fees
Fresh East End Apartment Walkable to Downtown Portland
Exterior
Private kitchen
Interior
Room
Exceptional
(6 reviews)

Sunny + private West End apartment with free parking

Portland

8% off
AU$2,525
for 7 nights, 1 apartment
AU$361 per night
includes taxes & fees
Sunny + private West End apartment with free parking
Scales! The best spot in the Old Port for upscale New England Seafood.
tour the Victoria Mansion at the bottom of the street
Room
the State Theater is a 5-minute stroll up the street
Exceptional
(58 reviews)

Bright & Sunny West End Apartment with Private Parking.

Portland

8% off
AU$3,848
for 7 nights, 1 apartment
AU$550 per night
includes taxes & fees
Bright & Sunny West End Apartment with Private Parking.
Pia Men Miyake, the best place for lunch!
Smalls! A short walk from the house.
Room
Dining
Exceptional
(24 reviews)

West End Bright Spot with Parking.

Portland

8% off
AU$2,810
for 7 nights, 1 apartment
AU$401 per night
includes taxes & fees
West End Bright Spot with Parking.
Mix of nautical and rustic elements throughout.
5 min car ride to Downtown/Old Port.
Festive lighting at your control.
Large deck with seating for six, festive lighting and a firepit. Views and sun!
Exceptional
(133 reviews)

City Amenities, Casco Bay Sunrises and Natural Beauty

Portland

8% off
AU$3,021
for 7 nights, 1 apartment
AU$432 per night
includes taxes & fees
City Amenities, Casco Bay Sunrises and Natural Beauty
Interior
Interior
Dining
Living area
Exceptional
(22 reviews)

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

Portland

8% off
AU$4,536
for 7 nights, 1 apartment
AU$648 per night
includes taxes & fees
West End's Diamond in the Rough 2-bedroom Apartment with Parking & WiFi
The plush carpeted staircase enhances both comfort and the home's inviting atmosphere.
Gather with family or friends in the comfortable living area after a day around the historic city.
Cook with ease in the spacious kitchen, complete with full-size appliances and ample counter space.
Gather under the string lights in the private backyard for coffee, drinks, or great conversation.
Wonderful
(14 reviews)

Experience Portland’s charm in this beautifully restored 2-bed, 1.5-bath Victorian apartment! Located downtown, enjoy modern comforts, historic elegance, a private backyard, AC, and 1 free parking spot. Perfect for your Maine getaway!

Portland

11% off
AU$2,740
for 7 nights, 1 apartment
AU$391 per night
includes taxes & fees
Experience Portland’s charm in this beautifully restored 2-bed, 1.5-bath Victorian apartment! Located downtown, enjoy modern comforts, historic elegance, a private backyard, AC, and 1 free parking spot. Perfect for your Maine getaway!

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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)
  • Brunswick Golf Course (16.6 mi / 26.6 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:

  • Little John Island Preserve (4.5 mi / 7.3 km)
  • 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)

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

What is the best area to stay in Cliff Island when booking a holiday rental?
When considering a holiday rental on Cliff Island, Maine, a popular area to stay is near the picturesque waterfront. This part of the island offers stunning views of the surrounding waters and easy access to the beach, making it an ideal choice for those looking to enjoy the natural beauty of the area. The waterfront location is also close to some of the island's top attractions, such as the charming local lighthouse and the scenic hiking trails that wind through the island's lush landscapes.There are a variety of properties available in this area, suiting different preferences and group sizes, from quaint cottages to larger family homes. Staying near the waterfront not only provides a tranquil atmosphere but also places you within walking distance of local shops and eateries, allowing you to fully immerse yourself in the island's laid-back lifestyle.
What are the top attractions in Cliff Island?
In Cliff Island, Maine, visitors can enjoy a serene and picturesque experience, primarily known for its natural beauty and outdoor activities. The island itself is a haven for those seeking tranquil surroundings and stunning coastal views. One of the main attractions is the Cliff Island Community Church, which embodies the island's charm and history.The island's beaches, such as the sandy shores at the eastern side, offer a great spot for relaxation and enjoying the Atlantic Ocean. Outdoor enthusiasts can explore the walking trails that meander through the island, providing opportunities for birdwatching and enjoying the local flora and fauna.For those interested in marine activities, kayaking around the island is a popular pastime, allowing visitors to engage with the coastal environment and perhaps spot some wildlife. Cliff Island's small community offers a chance to experience local life, with seasonal events that reflect the island's culture.
Are all fees included in the Cliff Island holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Cliff Island holiday homes with parking?
Stayz offers a wide selection of holiday homes in Cliff Island with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Cliff Island holiday homes?
You can find great discounts on holiday homes in Cliff Island on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Cliff Island holiday home booking on Stayz?
To find Cliff Island holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Cliff Island?
A long-stay holiday home in Cliff Island is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Cliff Island holiday home?
Book your Cliff Island holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Cliff Island?
Prices for holiday homes in Cliff Island vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Cliff Island to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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