Cliff Island Vacation Rentals

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Vacation Rentals in Cliff Island

Our top choices for Cliff Island vacation rentals

The Weldon Hotel

4.5 star property
9.8 out of 10, Exceptional, (76)
"Absolutely beautiful place to stay. "
$500 nightly
The price is $538
Sep 7 - Sep 8
Total with taxes and fees
The Weldon Hotel

Sensational Beachfront Property Old Orchard Beach, with indoor elevator

9.6 out of 10, Exceptional, (63)
"Our stay was perfect. The house allowed for us to sleep 17 people comfortably, eat together, cook in teams for a progressive dinner and spread out all at the same time. Jason was quick to answer questions, and he provided excellent suggestions for places to eat and shop. We could not be more pleased with our stay. Thank you, Jason!!"
$1,330 nightly
The price is $1,450
Sep 8 - Sep 9
Total with taxes and fees
Sensational Beachfront Property Old Orchard Beach, with indoor elevator

Grand Victorian on the Beach, Summer

9.8 out of 10, Exceptional, (75)
"Wonderful spot with great accommodations! Would definitely stay again!"
Grand Victorian on the Beach, Summer

Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator

9.8 out of 10, Exceptional, (216)
"We stayed off season to just get away. The beach view is really nice. We went to the restaurant downstairs for food and live music. Very convenient! Place was clean. "
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator

68 East Grand Ave

3.0 star property
8.6 out of 10, Excellent, (9)
"Property was very nice and close to the beach. Would stay there again. The front desk was extremely helpful as well. "
68 East Grand Ave

Bright and airy condo with beachfront access and walkable entertainment nearby

8.0 out of 10, Very Good, (1)
"Not a bad spot. Just don't expect too much in the way of frills and be prepared to be flexible with sleeping/parking arrangements."
Bright and airy condo with beachfront access and walkable entertainment nearby

Ocean Front Penthouse suite, Luxurious 2-bedroom,1350 sqft,2 decks, A++ location

10.0 out of 10, Exceptional, (20)
"Stunning property and great location! "
$518 nightly
The price is $565
Sep 2 - Sep 3
Total with taxes and fees
Ocean Front Penthouse suite, Luxurious 2-bedroom,1350 sqft,2 decks, A++ location

Cozy and Quiet Home One Bedroom Private Bathroom in Portland Maine. NOT KITCHEN.

2.0 star property
10.0 out of 10, Exceptional, (1)
"The property was as described, clean, and in a quiet neighborhood. Conveniently located to many local attractions. Check in and check out process was smooth. Overall enjoyed my stay very much. "
Cozy and Quiet Home One Bedroom Private Bathroom in Portland Maine. NOT KITCHEN.

New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

10.0 out of 10, Exceptional, (225)
"We had a wonderful stay at this cottage. Great location to explore the surrounding areas."
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

Little Miss Cottages

2.5 star property
8.4 out of 10, Very Good, (87)
"Cute and tidy cottage, easy walk to beautiful beach."
Little Miss Cottages

Gorgeous ocean-front home with stunning beach views

9.4 out of 10, Exceptional, (115)
"Second time staying hear. Will continue to repeat"
Gorgeous ocean-front home with stunning beach views

Private, 2nd Floor Cottage with Wonderful Ocean Views- Perfect for Families!

9.8 out of 10, Exceptional, (42)
"This place is a real gem. Really clean, well equipped and for our two kids it was perfect (toys inside and playground in the yard. The host is very kind and very quick to fulfill our needs. Thanks again!"
Private, 2nd Floor Cottage with Wonderful Ocean Views- Perfect for Families!

Cozy Coastal Condo with Parking – Walk to Beach & Town

2.0 star property
8.6 out of 10, Excellent, (11)
"The place was clean and spacious enough for our family of 4. A simple place within one block of the ocean. Can’t beat that! When we had an issue with WiFi, they responded promptly and all was rectified very quickly. Easy access upon arrival and clear directions about departure. Would recommend ."
Cozy Coastal Condo with Parking – Walk to Beach & Town

Beach House ∆ Prime Location ∆ Steps to the Ocean

10.0 out of 10, Exceptional, (45)
"Great location. House was clean. "
$497 nightly
The price is $542
Sep 15 - Sep 16
Total with taxes and fees
Beach House ∆ Prime Location ∆ Steps to the Ocean

350 Yards to the beach. Pet friendly!

8.0 out of 10, Very Good, (34)
"Clean, easy access to everything! Fantastic stay will come again! Thank you!"
$406 nightly
The price is $443
Sep 2 - Sep 3
Total with taxes and fees
350 Yards to the beach. Pet friendly!

New 2-bedroom cabin with WiFi, AC in delightful Old Orchard Beach

10.0 out of 10, Exceptional, (4)
"Very clean and comfortable, we enjoyed our stay."
New 2-bedroom cabin with WiFi, AC in delightful Old Orchard Beach

Spectacular Oceanfront Property Offering Bold Panoramic Views of Saco Bay !

10.0 out of 10, Exceptional, (36)
"The view is beautiful and has everything you need "
Spectacular Oceanfront Property Offering Bold Panoramic Views of Saco Bay !

Oceanfront Condo! Spectacular Views From Private Large Balcony

9.0 out of 10, Wonderful, (138)
"Great place. Perfect location if you want to be in the middle of it all."
$423 nightly
The price is $461
Sep 15 - Sep 16
Total with taxes and fees
Oceanfront Condo! Spectacular Views From Private Large Balcony

Relaxing Stay | Pool & Park

$148 nightly
The price is $159
Sep 2 - Sep 3
Total with taxes and fees
Relaxing Stay | Pool & Park

Beachfront Luxury Grand Victorian Condo (Primetime View directly down the pier)

9.8 out of 10, Exceptional, (126)
"This unit surpassed our expectations. Excellent location, the unit was impeccable, had everything we needed and more.Highly recommend renting from Owner.. I know we will be!"
Beachfront Luxury Grand Victorian Condo (Primetime View directly down the pier)
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Cliff Island Hotel Reviews

Find out more about Cliff Island

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 $159 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?

Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach: This vacation home rental outside of Cliff Island offers a garden, a selection of games, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

What can I see and do in Cliff Island?

Explore the area and family-friendly sights such as Portland Observatory, or get out into nature at a spot like Sand Beach. In the larger area, you’ll find Fifth Maine Museum 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.