
Holiday rentals with a kayak in Portland
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Top-rated Accommodation with a Kayak in Portland
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Holiday House Rentals with a Kayak

Little Sebago Lakefront Getaway
Violeta and her space were amazing. The house was exactly as advertised and we felt right at home for our long weekend. We are looking forward to making this a yearly visit!

Waterfront |Near Mountains |Outdoor Sauna |Firepit
One of the best Airbnb experiences! The location and surroundings were absolutely beautiful, and the house was exceptionally clean and comfortable. We had the chance to fish and kayak, which were the highlights - so peaceful and scenic. This was a truly unforgettable experience. We caught a couple of bass and pike, which was so much fun. The host was also very responsive and kind. We will definitely come back and highly recommend this place.

Lakefront Home-Stunning Views-Hot Tub, 3100 sqft!
We had an absolutely wonderful time at Julie's lakeside home for Father’s Day weekend. The setting was serene, with beautiful views of the water, making it the perfect spot to relax and enjoy quality time together. The home was well-equipped and comfortable, offering everything we needed for a memorable stay. Julie was a fantastic host, ensuring that our experience was seamless and enjoyable. We truly appreciated the peaceful ambiance and thoughtful touches throughout the space. Highly recommend for anyone looking for a lakeside retreat!"

Luxury 6 bedroom Beach House 50 ft from beach
This beautiful venue was worth every penny. Chris greeted us and made us feel right at home, even pointing out opportunities for viewing local wildlife! Our party of 10 (ages ranging from 14 to 74) never felt crowded, a floor for every family! The kids even played "hide & seek" in the house. We made memories that will last a lifetime. Try as we may, we can't think of one thing we would have changed about our stay. Thank you Chris, Jason and family for sharing this beautiful home!

Kayak to the Causeway-50s cottage with modern vibe
This has been by far the nicest place we have stayed. Super clean and nicely decorated. Wonderful communication by the hosts. Perfect weekend getaway.

Modern Maine Lake House near Portland
Had a small bachelorette party here for one of my closest friends. It was the perfect place for a more relaxed girls trip but close enough to get to downtown Portland for any shops, sightseeing, and food! Highly recommended.

Luxury Lakefront Paradise w/ Private Beach
My family and I had a serene experience staying here. Although the weather was mostly rainy or cloudy, we loved the lake location and maximized the indoor, outdoor, and nearby activity options. The hosts were so responsive, regardless of the question, and made this a truly delightful visit. This was my parents’ first Airbnb experience and it set the bar higher than I could have imagined! My family and I are already talking about coming back!!

Breathtaking Bay Views!
I wanted a peaceful place by the water to unwind and Maggie’s home nailed it. Every aspect of our stay exceeded expectations. The deck views were amazing—islands, ospreys hunting, and a duck and her ducklings feeding along the shoreline. At low tide we poked around in the sand at the bottom of the rocks, and could have easily walked out to the center of the bay but it was juuuust a bit chilly for us. Easy to drive, park and walk along beach on the Atlantic side and explore. We didn’t have time to kayak but hope to be back to give it a go. So much beauty and nature, but with all the amenities that make it easy to relax. Maggie was responsive, and she and her family obviously care very much for the property. Check the propane BEFORE you plan to grill :), and bring flip flops to easily get from the house to the grotto (which was so comfy and cozy) and back again.
Cottages with a kayak

Cobb Cottage: Lake Beachfront Fri-Fri Jul-Aug
Great cottage right on the lake! Kayaks were great to take out and explore the lake and see wildlife as well. The cottage is spacious and comfortable. The kitchen is large and well appointed for any cooking you may want to do. Grill and plenty of beach chair/ towels available as well. Adam is extremely responsive and I highly recommend. The place is quite peaceful though the lake gets pretty busy on the weekends with boats but not in an obnoxious way. Loved sipping coffee and reading on the dock each morning. Will definitely book again!

Waterfront cottage with spectacular sunset views!
We stayed at the cottage for about a week in late September and it was a perfect spot to get away from it all. The house is on a serene pond with trees reflected on the water, classic Maine. The cottage was clean and well kept with most everything you’d need. It’s in a very quiet neighborhood, so not a party spot, which worked out fine for our quiet family. We’d consider coming back to visit family. Thank you for the comfortable stay!

Romantic waterfront cottage for two in Maine
Perfect place to get away and relax. We enjoyed fishing in the morning and evening and sight seeing during the day. Quick trips into Portland, Kennebunkport, Freeport, and the Maine Botanical Gardens (highly recommended ). Locally we enjoyed the Maine Wildlife Park and u-pick strawberries. Picked up some wonderful seafood at Bob’s in Windham to cook in the well supplied kitchen. Mary Ellen and Brian have thought of the many little things that make the cottage a hospitable place. They answered our questions promptly leading up to our trip.

Coastal Waterfront Tiny home in West Bath
What an awesome airbnb! The views are stunning and surroundings couldn’t have been more peaceful. The cottage itself was exceptional and had everything I needed and more. Wish I could've stayed there longer! 10/10 would recommend this place to anyone!

Cozy camp near highland lake
Lori was a wonderful host for our trip up to Maine. My girlfriend and I enjoyed doing yoga in the entrance room when it rained and a nice sunrise kayak trip out on the lake across the street. My in-laws stayed with us too and we all had great laughs together and enjoyed good food all weekend long.

Driftwood Dreams Cottage
As we arrived there was a bottle of wine waiting for us! We so enjoyed sitting on the deck watching the tides and the eagles soaring above us, diving into the water to catch fish! We kayaked right off the property which was also super convenient and very beautiful. We had a lovely week at the cottage and thoroughly enjoyed its amenities. We would definitely recommend and return!

Private oceanfront cottage, great views, and float
the stay was nice, the place was clean, match the description, pretty easy to find, and Christine had great communication. very beautiful views, right on the water, kayaking was nice.

Charming Designer Cottage on Marsh
Tiny but beautiful cottage with walls of windows in the living room and bedroom overlooking the salt marsh. It was like staying on a boat! Great kitchen, comfortable bed and cozy fireplace. Beautiful in the winter.
Cabin rentals with a kayak

Lake Cabin in the Trees
We fell in love with this beautiful, magical “tree house”. You couldn’t ask for a more perfect place to share time with friends & family. Beautiful view of the lake & everything you need is there - both inside & outside. This home radiates happiness & reflects the thoughtfulness of the owners. The furnishing are lovely & they have the most comfortable beds I’ve ever slept in. I heartily recommend this cabin the woods. We look forward to returning. Linda

Private Hilltop Cabin, Lakes and Trails Abound..
We had the absolute best time at MJ’s place, highly recommend !! The house is spatious yet very cozy and quiet, with a nice back porch to sit and enjoy the surrounding woods! Home is also very close to town and to Poryland/coastline, and the cleanest lake to swim in that we’ve ever been to! MJ was very helpful and quick to respond. Stay here! We hope to return sometime soon!!

McKeen's Riverside Retreat
We have stayed at Jackies place twice now and enjoyed it just as much this time as the last. Even though it rained for two days the house is plenty big enough to spread out. We had to change our reservation days twice because of circumstances and Jackie was very accomidating..

Lakeside Cabin Nestled in the Pines
We had a wonderful stay at Ricky’s cabin on Bear Pond! It was peaceful, with beautiful views of the water, and we loved having campfires in the evenings. The cabin was clean, cozy, and had everything we needed for a relaxing getaway in the Maine woods! Ricky was a great host—friendly, responsive, and made sure we felt right at home. We would highly recommend staying here!

Get away at Crystal Lake
Had an amazing stay here, so wondering could go fishing at the dock, the basement was so fun to play pong and just hang out, loved being able to watch disney+, just overall a wonderful stay and amazing and friendly people.

Private cabin w hot tub,skiing,firepit & mountains
We absolutely loved our stay at Alexa’s cabin. We enjoyed the hot tub, fully stocked kitchen, and truly felt like we could disconnect from the world to connect with those around us. Alexa was a great communicator, provided detailed instructions and local recommendations that were spot on. Don’t hesitate to book this Bridgton escape!

Roxie the Tiny Cabin on 100 acres
We stayed at the Roxie cabin. The cabin itself was wonderful. The cabin was well stocked with anything you may need from playing cards to bug spray. We threw axes then took one of the canoes out and enjoyed the peaceful pond. Pizza making was definitely a highlight of the evening. I’d definitely recommend staying.

Maine Lakes-Pleasant Mt-Private Trails
Third visit in three years for a weekend fishing getaway. Great location, beautiful property. Excellent hosts. Looking forward to a return visit.
Quick stats about holiday rentals with a kayak in Portland
Total rentals
20 properties
Nightly prices starting at
$155 AUD before taxes and fees
Total number of reviews
2K reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wi-Fi availability
20 properties include access to Wi-Fi
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