
Vacation rentals with a kayak in Southport
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House rentals with a kayak

Tidewatch. Escape to the water.
Our family of five had an amazing time at Nicole’s place. The house is situated in a prime location on the water, with access to so many activities right from the dock. At night, you can hear a pin drop. It’s quiet, peaceful and perfect for stargazing and roasting marshmallows. The house is comfortably appointed with lots of blankets and pillows, tons of kitchen utensils, pots & pans, comfortable bedding, etc. The decor is very coastal Maine, lending itself to a cozy nautical vibe. You’re incredible close to Boothbay Harbor and the Coastal Botanical Gardens as well as neighboring cities like Wiscasset, Damariscotta, Bath and Portland. Nicole has great recs for food and local activities. Overall, her place is so comfortable and inviting, it was super hard to leave. Definitely recommend!

2 Acre Waterfront w/Canoes & Kayaks, Game Room
If you want a private, well furnished home in the woods with fishing access on the stream and 2 fire pits this is your place!! Staying at this house made a work trip for my crew and I, feel like we were on vacation for 2 nights while staying there. Worth the money and great hosts!

Postcard views, ocean front and idyllic cove
Mihai is a wonderful host and his place is a gem! The gorgeous location is nothing short of magical and the house is immaculately designed and decorated. The hot tub is an amazing bonus. Everything about our stay went smoothly and even during off season, we found plenty to do. Would absolutely stay again.

Maine Waterfront Hideaway
This place is as-described and then some. Private, secluded, and peaceful. You have the water to yourself and virtually no noise around you (other than what your group makes!). Wallace’s has pretty much anything you need grocery-wise and good breakfast and lunch sandwiches. Pizza is good, too. The house is stocked with all the basic necessities and consumables, and then some. Probably the best-stocked ABNB I’ve stayed at (all the way down to q-tips in the bathroom). Friendship is far off of the tourist path, but not too far to go see things. The house was a perfect fit for our group of six adults and four teens. They never ran out of things to do (including fast WiFi, unfortunately—dad speaking there, not a knock against the house). The owner was very responsive to messaging. I can’t recommend this place enough.

New Modern Cottage with Ocean Views & Wildlife
We can’t say enough good things about this stay. We came for our honeymoon, and were met with flowers and a few other treats from the host as a gift. How sweet! As far as the property, the cottage is perfectly sized for two or three, and is designed delightfully. It is on a shared lot with the family’s primary residence , but feels very comfortable and private. A close by walk to the water as well. Inside, you will find everything you could ever need from pots and pans, spices, towels, and the best recommendations for the area. We’d build our own version of this cottage to take home with us if we could. We hope to one day be back and will always remember our amazing time in Harpswell.

Family Escape w/ Kayaks, Fire Pit, & Water Access
What a whimsical town! In the middle of nowhere So peaceful Yet, Wallace's General Store, right up the road Maybe a mile Amazing food and Sandwiches and just about everything under sun to Need So, just down the road is this Amazing Place! Three Sisters Farm Heaven Awaits Must check out

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.

Salty Breeze Cottage
Fantastic stay at Sherri’s place. Fully stocked cottage nestled in the woods overlooking the water. Brand new kitchen and bathroom. Conveniently located to Bowdoin College and downtown Brunswick. We would definitely stay again, I highly recommend Sherri’s place.
Cottage rentals with a kayak

Lakefront Home, Sandy Beach, Belgrade Lakes, Colby
Hillary was very responsive to all the emails I sent. She was friendly and helpful with questions I had. The cabin was well furnished and the kitchen was well equipped with modern appliances. If I was ever in the area in the future, I would love to stay here again.

Your private waterfront B&B retreat in Maine...
I stayed at Liz and Alex’s stunning place at the beginning of September. This was either my 3rd or 4th time and I love being there. The quiet and the utter peacefulness of being literally on the banks of the estuarial river is amazing. Although I was only able to be there for 2 nights this time, I was recharged and ready to go back home when I left. On other visits I’ve taken advantage of being near the delightful town of Damariscotta, Pemaquid Point Lighthouse, Hidden Valley Nature Preserve, Muscongus Bay Lobster dock, the Audubon preserve in Bremen, and so many others. On this visit I stayed put, letting the inward and outward flow of the river soothe me while I read and wrote. On this visit I also had a nice long chat with Liz, a remarkably talented woman. See her book and ask about her films when you go.

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.

Harbor Hideaway
My wife and I go to Boothbay Harbor every anniversary. We had a great place last year and it was not available. So we gave Julie‘s place a try. We were not disappointed. It was incredibly private. It was exactly as advertised. The waterfront was gorgeous. The campfire area was perfect. And the location to town was also just exactly right. Julie was incredibly responsive when we had questions. We felt right at home. Oh, and the kitchen was very well appointed. Great for cooking. Would definitely go back and recommend it to others. One of the best.

Private oceanfront cottage, great views, and float
Christine’s place was very clean and cozy and the location on the water couldn’t be beat. We were in town to visit Bowdoin, so didn’t take advantage of the kayaks, but loved waking up to the water view each morning. Everything you need is within a 10 minute drive and while we didn’t cook, the kitchen looked well stocked.

Charming Designer Cottage on Marsh
Location, location, amazing location. Backed up against a beautiful marsh, walking distance to goose rocks beach, close to restaurants like Earth at Hidden Pond, and downtown. As advertised, the pictures are the reality. Nice bathroom with tiled shower and heated floors. Well equipped with everything you may need. Kayaks, beach toys, quiet neighbors. Adorable exterior, fire pit, outdoor furniture. There is a lot of value and it’s a well managed rental. Hosts were very responsive and helpful. Felt like a home.

Classic Lakefront Maine Cabin
What a beautiful location! David is a great host. He made sure we had good directions, tips for the area, and was quick to answer any questions. The lakeside cabin has absolutely everything you need to have a peaceful, relaxing vacation. The view of the lake is spectacular. The cabin is very clean, has a well stocked kitchen, comfortable beds and Echo lake is a gorgeous pristine lake. Every morning, we enjoyed our coffee on the dock. We swam, kayaked, canoed and even tried out the paddle boards that came with the house. We would love to come back! Thanks!

Bass Point Lakeside Cottage: Livermore, Maine
I had a wonderful 4 night stay at the lake house and couldn't have asked for a better place to spend the little getaway. It is beautifully located on the lake and has this huge window in the living room from which you have an amazing view. The house has everything you need, even washing machine and dryer in the basement. I would 100% recommend this unique place! Christine has been super helpful throughout my stay.
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!!

Cozy Camp Round Pond - Kayak, Swim, Bonfire, Games
We had a great stay at Leah's cabin. The place was warm and cozy, and we enjoyed the lookout onto the beautiful frozen lake. Leah was very proactive and responsive. A great stay!

Sauna + Stay in MidCoast Maine - Cabin 3
What a wonderful spot! Gorgeous, quiet pond and relaxing wood fired sauna. Rheanna is a super responsive and helpful host. We'll be back! Just FYI - this cabin is a "three season" structure. Although it was super comfortable, it felt a little more like camping than we originally expected with some cool nights and mornings, a few insect frinds, and a short walk to the shared bathrooms and kitchen area.

Rustic Family Cabin on China Lake
We come every year. It’s a great quiet place.

Hobb’s House - Year Round Log Cabin on the Water
It was such a great weekend spot. Quiet and peaceful but close to everything. The water was stunning.

Thompson Lake, No Cleaning Fee Pine Point Cottage,
Really good communication! Very welcoming. Private and quiet area. Immaculate inside. Had access to kayak, outside firepit and pond. Outside furniture to enjoy the pond and property.

Rustic, cozy cabin on Sebago Lake. A hidden gem.
The cabin was cozy, the view of the lake was incredible, and Bonnie was a great host!
Quick stats about vacation rentals with a kayak in Southport
Total rentals
10 properties
Nightly prices starting at
ﺩ.ﺇ735 before taxes and fees
Total number of reviews
310 reviews
Family-friendly rentals
10 properties are a good fit for families
Wifi availability
10 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool
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- Sebago Lake
- Scarborough Beach
- Popham Beach State Park
- Surfside Beach
- Samoset Resort
- Pemaquid Beach
- Fox Ridge Golf Club
- Coastal Maine Botanical Gardens
- Cliff House Beach
- East End Beach
- Brunswick Golf Club
- Belgrade Lakes Golf Club
- Palace Playland
- Pemaquid Point Lighthouse
- Ferry Beach
- Funtown Splashtown USA
- Dunegrass Golf Club
- Wolfe's Neck Woods State Park
- Freddy Beach
- Crescent Beach State Park
- Portland Museum of Art
- Maine Maritime Museum
- Prouts Neck Country Club
- Bradbury Mountain State Park