
Holiday rentals with a kayak in Portland
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Top-rated rentals with kayak in Portland
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House rentals with a kayak

Windham Wind Down-Lakefront, Dock, Kayaks, & SUPs
Our group was two small families with kids ages 6 and 8. Everyone had a great time. If you’re looking for a home to get out into nature, this is it. The private dock and lake gave us hours of time to play outside. Kayaks, paddle boards, and fishing off the dock was fun and all part of the house. Kids had a blast and so did the adults. Perfect for family summer vacation. We had a few rainy days but either played board games inside or went into Portland which is only 20-30 minutes away. Visited Mackworth Island in Casco Bay. Must do if you want to have a day excursion. The house well kept and easy to navigate. We spent more time outside on the lake than inside.

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!!

Lakefront | Dock + Fire Pit Near Sebago & Portland
Beautiful lakeside property! Our family loved our weeklong stay complete with paddle boarding, cozy movie nights, and a generous welcome basket that we enjoyed for our s’mores night. Super comfy beds and cozy interior. Kevin was a fantastic host and was super responsive to all of our questions. If you’re looking for a peaceful getaway with lots to do while you unplug (or choose to stay plugged in) look no further.

Charming 4 bedroom lake front, with private beach
We loved this home! It was apparent that the house had been updated indoors with a fresh look, refreshed paint, new floors, new appliances . The outdoor canoes, paddle boats, paddle boards were enjoyed by all. If I could rate this location with a 10, I would. Kudos to this location and to Patricia as a host for an immensely enjoyable experience. This is a definite return location!

Luxury Lake House w/ Home Theater, Hot Tub & Gym
I had a race this past weekend and needed a short stay for my extended family- this place hit all the marks, and more! From cleanliness to well-stocked items throughout the house, this property is very well managed with a great layout and lake location for families. Will not hesitate to come back for a longer stay!
Cottage rentals 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.

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.

Quintessential Maine Lakefront Cottage.
We were looking for a quiet place near the water to relax and unwind. Marina's place was perfect! We enjoyed kayaking, and great views of the lake whether reading on the deck or playing boardgames in the dining room on a rainy day. We'd definitely stay here again.
Cabin rentals with a kayak

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!

Peaceful and Rustic Lakeside Cabin
This spot was AMAZING, and Eva was such an incredible host. For a large party like mine, all of us felt comfortable, and there was more than enough space where we were not cramped in. The recommendations that Eva provided were accurate and very resourceful. I have reached out to her a few times to ask questions and extend my gratitude for being such an amazing host, and she was by far one of the friendliest hosts I have ever encountered. My family and I were disappointed that we needed to leave, but we will most definitely be coming back again next year!

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.

Lake Front with Private Dock - BRAND NEW Furniture
This is an absolute beautiful place to stay. There is no question, I would 100% stay here again. My family had an amazing time here. Darryl was very easy to communicate with and made the stay very easy. If you’re looking for a clean and quiet place to stay, look no further.
Quick stats about holiday rentals with a kayak in Portland
Total rentals
20 properties
Nightly prices starting at
$129 SGD 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
Wifi availability
20 properties include access to wifi
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