
Holiday rentals with a kayak in Waterboro
Find and book unique kayak rentals on Airbnb
Top-rated rentals with kayak in Waterboro
Guests agree: these rentals with kayak are highly rated for location, cleanliness and more.

Luxury Year-round Treehouse with private hot tub
The Canopy is one of 5 luxurious tiny homes that make up Littlefield Retreat, a tranquil woodland village of 3 treehouses and 2 hobbit houses – each with its own private hot tub and dock. To see all five dwellings, click on the photo to the left of “Hosted by Bryce”, then click “Show more…”. This 15-acre forest retreat on Littlefield Pond offers our guests an experience that feels like a trip up to the woods of northern Maine, but is closer to home and to all the attractions of southern Maine.

Peaceful Cottage on Maine Flower Farm
Maine’s Peaceful Off-Season Escape Nestled next door to Ferris Farm, our family-run flower farm, this charming cottage offers a private place to rest and recharge. Enjoy slow, coffee-filled mornings, quiet walks, and cozy evenings by the fire pit. Use the cottage as your home base to explore nearby beaches (30 minutes) or head into Portland (35 minutes) for breweries, coffee shops, and great dining. Perfect for a couple retreat, solo escape, or remote work getaway, with dedicated workspace.

RK North : All season Waterfront cottage with dock
Waterfront get away !You will love the cottage in any season - right on the pond! Enjoy a private dock, swimming and floating right at your door. Relax at the fireplace under twinkle lights , enjoy birdwatching, hiking and swimming during your stay. Lots of ATV and snowmobile trails near by. A close drive to Kennebunkport where your find beach’s , shops and restaurants galore. The cottage has 2 kayaks and a canoe for use during your stay. There are 2 Smart TVs for streaming. Shows and DVD

Lobstermen's ocean-front cottage
Be our guests & experience the life & beauty of Midcoast Maine. Relax & enjoy the views, warm up in the sauna or go for a refreshing dip. The cottage is part of an over 100 year old working lobstering, and now oyster farming property we call, Gurnet Village. Located right on historic Route 24, we are conveniently situated between Brunswick & the islands of Harpswell. All rooms have ocean views. The tidal beach & the floating dock (May-Dec) is ideal for seasonal fishing, lounging & swimming.

Eclectic Lakefront Cottage on Great East Lake
Welcome to a relaxing stay on the shores of Great East Lake! The fall and winter are the definition of peace and quiet. Often you'll be the only folks on the cove! Come back inside after your outdoor adventures and warm your feet on the radiant slate floors .You can also prepare a home cooked meal in the vintage, fully applianced kitchen. This home is the perfect base for all your winter excursions, or enjoy family time inside with plenty of games, puzzles, ping pong, or air hockey! Enjoy!

StreamSide Getaway- HOT TUB / AC/ Wi-Fi
The Streamside Getaway offers a luxurious glamping experience in a new solar and wind-powered Geodome. Equipped with custom furniture, new hot tub,luxury appliances, free high speed wifi, AC/Heat Unit and modern bathroom and kitchen facilities, guests can enjoy a homely and comfortable stay in nature. A glamping site built in 2022 offers a contactless check-in process with a custom key code. Additionally, we have added archery, axe throwing, and kayaks to enhance your outdoor activity!

Lakefront Getaway
Looking for a quiet peaceful getaway? Our Maine post and beam home is set on 7 acres of lake front. Great getaway to enjoy marshmallows and a roaring fire, kayaking, canoeing, swimming, boating or enjoy a great movie. For downhill skiers proximity to King Pine, Sunday River, Shawnee Peak and Black Mountain. Cross country and snow shoeing on property and on the lake. If you have a snow mobile- great trails available. Finally, great shopping in nearby North Conway at the outlets.

LUX Designer Private Waterfront Hot Tub - Secluded
Escape to a luxurious, privately designed glass-walled waterfront cabin on 3+ secluded acres along the Crooked River in Naples, Maine. The river wraps around, offering total privacy, your own sandy beach, dock with direct Sebago Lake access, and state park minutes away. Unwind in the year-round hot tub, outdoor shower, hammocks, or by the see-through fireplace. Luxe bath with heated floors, huge walk-in shower w/ scenic window. AC, pets welcome. Perfect peaceful retreat—come recharge!

The Loon's Nest Cottage
Located only 30 minutes from Portland this adorable and cozy cottage sits 10 feet from Watchic Lake. Listen to the loons all day, paddle to an island, stare at the glassy lake from the breakfast nook, swim forever, read a book in the screened-in porch or toast marshmallows in the firepit, whichever it may be you'll simply enjoy the peace and tranquility of this very private Maine lake house nestled in the woods. If you’re feeling like a hike, a dinner out there are options a plenty!

Beautiful Lakeside Cottage
Beautiful, quiet and secluded lakeside cottage. Enjoy amazing sunsets on our pristine lake. Swim, kayak, fish or just relax and take in the natural beauty. COVID UPDATE: We know everyone has different levels of concern regarding the virus. Please know that while we feel our sanitation and cleanliness of the Cottage is exceptional, we have doubled our efforts providing multiple cleanings between guests. This is a NON-SMOKING property. We are sorry, but we cannot accommodate pets.

RiverPine Retreat - Clean & Bright Waterfront Home
Tucked away in a small town, minutes away from the New Hampshire border, located 2 minutes off of rt. 25 (direct route from Portland ME to NH) The ultimate family or couples getaway. Plenty of room in the back yard for any and all yard games, while also enjoying the firepit, "game shed" and 75ft of water frontage where you can swim, fish, or launch your kayaks from the dock into the Ossipee River. Wireless internet is available and reaches the back yard. The 'cabin' has 2 bedrooms.

Sokokis Lake House
The perfect place for friends & family getaways. The boat dock & fire pit are perfect for relaxing. It has everything you want: fully stocked kitchen, linens, towels, grill, dock, stand up paddle board, kayaks, life jackets, games, books wifi, cable, smart tvs, free parking & many more amenities. 2 hours from Boston 45 min to Portland, Lake Winnipesaukee, Old Orchard Beach, Sebago. Snowmobiling & lake in the back yard! Groceries, restaurants, & general store all within 1/2 mile.
Popular amenities for kayak rentals in Waterboro
House rentals with a kayak

Waterfront Gem walkable to Restaurants!

Beautiful lake-side home close to Portland Maine

Elevated 4-Season home - Mtn Views +A/C + Firepit

Warm Lakefront Log Cabin · Hot Tub · Game Room

Waterfront w Kayaks, Pool table, Pergola, Firepit

Blue Breeze - Private lakefront w/ Hot Tub

Historic Kennebunkport home .3 mile to Dock Square

5 Acre Lakefront Getaway
Cottage rentals with a kayak

Smokey Pines Camp

Tranquil waterfront cottage

Cottage on the lake! Includes kayaks & rowboat!

Thompson Lake, No Cleaning Fee Pine Point Cottage,

Cozy camp near highland lake

Coastal Waterfront Cottage in West Bath

Cozy cottage near Gilford, lake access & hot tub!

Waterfront Escape
Cabin rentals with a kayak

Idyllic Lakeside Cabin Winter Getaway

Rustic Log Cabin on Pawtuckaway Lake

Cozy Log Cabin

Rustic, cozy cabin on Sebago Lake. A hidden gem.

The Conscious Cabin | Getaways + Retreats

Dreamy Lakefront: Hot Tub, Kayaks, & Kid-friendly

Get away at Crystal Lake

Bear Cabin
Quick stats about holiday rentals with a kayak in Waterboro

Total holiday rentals
Explore 20 holiday rentals in Waterboro

Nightly prices starting at
Waterboro holiday rentals start at £103 per night before taxes and fees

Verified guest reviews
Over 1,160 verified reviews to help you choose

Family-friendly holiday rentals
20 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
20 of Waterboro holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Waterboro rentals

4.9 Average rating
Waterboro stays are highly rated by guests – averaging 4.9 out of 5!
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- Rentals with a washing machine and dryer Waterboro
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- Rentals with a fireplace Waterboro
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- House rentals Waterboro
- Rentals with outdoor seating Waterboro
- Rentals with lake access Waterboro
- Family-friendly rentals Waterboro
- Rentals with a firepit Waterboro
- Rentals with a patio Waterboro
- Rentals with a kayak York County
- Rentals with a kayak Maine
- Rentals with a kayak United States
- Hampton Beach
- Sebago Lake
- Ogunquit Beach
- Wells Beach
- Squam Lake
- Story Land
- Weirs Beach
- Long Sands Beach
- Popham Beach, Phippsburg
- Scarborough Beach
- York Harbor Beach
- Popham Beach State Park
- North Hampton Beach
- Willard Beach
- Short Sands Beach
- East End Beach
- Cape Neddick Beach
- King Pine Ski Area
- Gooch's Beach
- Gunstock Mountain Resort
- Cranmore Mountain Resort
- Waterville Valley Resort
- Wolfe's Neck Woods State Park
- Crescent Beach State Park





