Vacation rentals in Cliff Island

4.91 out of 5 average rating, 85 reviews

Cottage in Windham

Tranquil waterfront cottage

Jo-AnnRating, 5 stars6 months ago

This Lakeside Retreat was a perfect weekend escape for two couples. In late September, we seemed to have the pond to ourselves and enjoyed sharing time around the firepit overlooking the lake. The Bathroom was spacious and one level up from the bedrooms downstairs. The kitchen had everything needed to prepare an excellent meal. I would highly recommend this cabin to a a small group of friends or family looking for a great location near Portland and Lake area attractions.Our host Bobbi was very responsive.

4.89 out of 5 average rating, 204 reviews

Condo in Kennebunk

Over 1000 Five Star Reviews! Walk to Dock Square !

AshleyRating, 5 stars2 weeks ago

I had a wonderful stay at this cozy Airbnb. The location was perfect, right in the heart of downtown, so it was super convenient to walk to shops, restaurants, and everything else we wanted to see. We also loved that it was dog friendly, which made our trip even better. The place was clean, comfortable, and exactly as described. The host was friendly and responsive, making check-in a breeze. Highly recommend!

4.98 out of 5 average rating, 330 reviews

A wooden dock extends over vibrant green marshland, leading to a serene body of water. Lush trees and rolling grass create a peaceful backdrop, emphasizing the natural beauty of the surroundings.

Apartment in Arundel

Cape Arundel Cottage 1 mile to downtown KPT

WarrenRating, 5 stars3 weeks ago

Hillary's place was a wonderful place to stay for a cozy weekend getaway. It felt very homey with personal touches. We were here during a little snowstorm so we didn't spend any time outside but the yard and private deck were really nice. We had some troubles with the hot water but Hillary was very responsive and helpful! We would definitely stay here again.

5 out of 5 average rating, 3 reviews

A charming cottage is nestled among vibrant trees, displaying shades of orange and yellow. Outdoor seating is provided by several blue chairs arranged on a manicured lawn, with a pathway leading to a sunroom that features numerous windows allowing natural light to flood the space.

Home in Wells

"In Tempore" Cottage

AllisonRating, 5 stars9 months ago

Gisele and her property manager were promptly responsive. The cottage was extremely clean, newly decorated and well appointed. The layout was very comfortable for our family of four. The pools were nice and not overly crowded. The only negatives were: If not taking the trolley or golf cart, the closest pool was a half mile walk with no parking available. The further pool did have parking. Also, no outside water source/hose to rinse off. Plenty of restaurant choices nearby in Wells, Ogunquit and Kennebunkport. Wells beaches were beautiful with easy, affordable parking. Overall a wonderful stay in Wells!

5 out of 5 average rating, 6 reviews

A wooden dock extends into a calm lake, leading to a small boat anchored at the end. The water reflects a clear blue sky, with gentle ripples across the surface, and green hills visible in the distance.

Home in Harrison

2BR Lake House on Private Beach w/hot tub & sauna

JasonRating, 5 stars6 months ago

This is place is a gem. The lake is beautiful and the beach is very private. The house has a nice layout and is both spacious and cozy. This was our second year staying here and we plan to come back again! Dina is very responsive and great to work with.

Townhouse in Kennebunkport

A sandy beach scene is captured, featuring colorful kayaks arranged neatly in the foreground. Sunbathers and beachgoers enjoy the sunny weather, with umbrellas dotting the shoreline. A smooth ocean extends to the horizon, framed by a clear blue sky.

4.94 out of 5 average rating, 167 reviews

Great get away spot,historic home in Kennebunkport

TreenaRating, 5 stars4 months ago

I can’t say enough about this experience. The house was a great location for my mother’s 70th and Jennifer went the extra mile (literally) to make this a memorable experience for the celebration weekend. She is so easy to communicate with. Exceptional host, all the way around!

Townhouse in Old Orchard Beach

An inviting entryway is presented with a white wicker table and two blue-accented chairs. A large sign displays the name 'Beach House' against a turquoise background. Decorative items, including a glass jar and framed message, enhance the welcoming atmosphere, complemented by light-colored siding.

4.89 out of 5 average rating, 9 reviews

Unit 3 Getaway - Perfect for Families!

DanielleRating, 5 stars8 months ago

Perfect size for our family of 4. Location to the beach was a short walk across the street. Kitchen was modern and clean. The beds were comfortable. Pillows were available to use but we brought ours from home. Two bathrooms are always a plus with two teenage girls, only request from them was a full length mirror in the 2nd bedroom to check out their outfits. Owner reached out during our stay to check in and see if everything was going well. Very thoughtful. Would highly recommend a stay here.

Apartment in Kennebunkport

A wooden dining table is surrounded by six matching chairs on a spacious deck. A small vase filled with colorful flowers sits at the center of the table. Beyond the deck, trees provide a lush backdrop, with green views extending toward the distant golf course.

4.93 out of 5 average rating, 29 reviews

Charming Kennebunkport

EmilyRating, 5 stars7 months ago

My husband and I stayed at Kristen’s apartment for 2 weeks at the end of August and had the most amazing time! This was our 3rd time to KPT and most definitely our favorite thanks to this gorgeous Airbnb and Kristen’s hospitality. The apartment was perfect for us — was exactly as described, better than the photos with amazing windows and views, speedy WiFi perfect for working remotely. It’s a quick 4 minute drive into town, and such a beautiful area to walk around. Kristen was so responsive and helpful — there’s a super extensive list of local reccs in the apartment, and a beach pass that you can use during your stay. We loved this home away from home, and can’t wait to come back soon!

4.83 out of 5 average rating, 139 reviews

A bright dining area features a large glass table surrounded by six black wooden chairs. Natural light filters through three large windows, and a simple floral centerpiece sits at the table's center. A modern chandelier hangs above, complementing the neutral-toned walls.

Apartment in Portland

Fall in LOVE With PORTLAND, MAINE

OliviaRating, 5 stars1 month ago

Stayed for a weekend with 5 people - the space was perfect us! With 3 beds and 2 baths we didn’t feel on top of each other inside. We opted for free street parking which was never an issue. There’s a handful of coffee shops, restaurants and bars with 5-10 min walk. Old Port is about 20 min walk but very easy and safe. We loved being around the block from the ocean and east prom!!

4.98 out of 5 average rating, 51 reviews

Home in Boothbay

Postcard views, ocean front and idyllic cove

CharlesRating, 5 stars6 days ago

Quiet and serene. We visited with 3 kids and our dog. We spend spring break here and being early in the season most stores and restaurants were jot yet open. We managed amd had good quality family time. Loved the area which had ample Preserves to go on one or two walks each day. The house was clean and had ample supplies from towesl to kitchenware. Highly recommend this spot. Thank you!

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Popular amenities for Cliff Island vacation rentals

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Other great vacation rentals in Cliff Island

4.93 out of 5 average rating, 58 reviews

A modern kitchen is highlighted with sleek white cabinets and a polished granite countertop. High-end stainless steel appliances, including a gas range, are featured. The open layout connects to a bright living area, where natural light fills the space through large windows.

Home in Scarborough

Gorgeous 4 BR home with HOT TUB

Elizabeth AnnRating, 5 stars1 week ago

The home was beautiful and matched the photos online. Clean and inviting! Gregory was responsive while booking and during our stay. Very kind and would stay here again for another girls weekend get away!

4.97 out of 5 average rating, 63 reviews

Home in Gray

cozy 3 bedroom ranch with deck and screen porch

MichaelRating, 5 stars3 months ago

The house is lovely and, if it’s not new, it sure feels that way. In a very quiet area with tons of outdoor space yet just a mile or two from more main roads. Had a lovely white Christmas/Hanukkah with fresh snow on the 24th. Diana was a great host, always answering questions promptly and rolling with some last minute travel issues. Would love to stay here in warmer months to take advantage of the outdoors and the lovely sun porch.

4.75 out of 5 average rating, 20 reviews

A covered porch features a comfortable seating area with a wicker sofa and matching cushions, arranged around a low coffee table. A hammock is suspended for relaxation, and a striped outdoor rug adds texture to the wooden floor. Large windows provide views of the surrounding landscape.

Home in Otisfield

Log Cabin *15 acres*hunting* snowmobile*skiing

NinaRating, 5 stars3 months ago

great place for a group of friends to get away from the city ! hot tub was spacious, pool table was a great addition to the house, and the large property was awesome for exploring the woods. overall, 10/10 would definitely come back !! only downside, there were only 11 forks for 12 guests !

5 out of 5 average rating, 101 reviews

Two black Adirondack chairs are positioned around a stone fire pit on a stone patio. In the background, a serene view of Winnegance Creek is visible, framed by trees and a cloudy sky.

Home in Bath

Waterfront Farmhouse with Modern Flair!

Tony & KellyRating, 5 stars2 months ago

The home was very welcoming and accommodating for our family of 5. The views were spectacular at sunrise, sunset and during the snowstorm. Bald Eagles and hawks would land in the trees right in front of the house. Also, there was a skating pond down the street my family love to visit almost each evening. There was an alarm going off as soon as we arrived, Debbi was incredibly fast responding and sending someone to check it out clear it up. On the plus someone came and plowed the driveway after the snowstorm it was great. She left a basket of local food and my family ate it up. We are so thankful for our relaxing week and would love to return.

Home in Old Orchard Beach

A bright kitchen space showcases white cabinetry and stainless steel appliances. A large island with granite countertops features seating for three, complemented by pendant lighting. An adjacent dining area is visible with a table designed for six, creating an open, inviting environment.

4.98 out of 5 average rating, 89 reviews

Woods Lane Golf and Beach Vacation

MarjorieRating, 5 stars7 months ago

Our group of 5 adults were so pleased we chose to stay at Jason’s house in Old Orchard Beach. We first looked at places in Portland, but Jason’s spacious house offered a quieter setting, with parking and more amenities, at a better price. Comfortable beds, immaculate throughout. Very thoughtfully appointed, with nightstands on both sides of the beds, and superior blackout blinds in the bedrooms. And we ended up spending less time in Old Port, because we enjoyed exploring the towns south of Portland: Old Orchard Beach, Saco, Biddeford, and we found good restaurants (including Holy Donuts!) nearby. We had no issues: we contacted Jason to confirmed our arrival/departure and he responded within minutes. We highly recommend!

Apartment in Old Orchard Beach

A spacious living area features a light-colored sectional sofa positioned around a wooden coffee table. Large windows provide natural light, and a dining area with wooden chairs can be seen in the background. Soft carpeting enhances the comfort of the space.

5 out of 5 average rating, 50 reviews

Horizon View Hideaway with Deck

ReneeRating, 5 stars6 months ago

The house is beautiful and very comfortable. We had everything we needed. The host was very friendly and responsive. We would definitely stay there again.

Home in Old Orchard Beach

A spacious bed with crisp white linens is placed in a room filled with natural light. Large windows frame stunning views of the sandy beach and ocean. A decorative navy blue throw blanket and patterned pillows add subtle touches of color to the inviting space.

4.84 out of 5 average rating, 31 reviews

Beautiful Spacious OOB Beachfront home w/ elevator

AnaRating, 5 stars2 days ago

We went off season and it was a very beautiful and tranquil beach experience. The house is gorgeous and spacious. Jason was very responsive and friendly. We will definitely be back!