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

Historic Kennebunkport home .3 mile to Dock Square
Under 10 min walk to Dock Square, 2 min walk to Kennebunk River. Luxury linens, Casper pillows, SandCloud towels, Malin + Goetz toiletries, well-appointed kitchen and beach chairs included in your stay. 2 bikes & 2 kayaks available. Walk to Colony Beach, bike to Kennebunk Beach. 2 min walk to Perkins Park on the River, steps down to water for launching kayaks. Dock Square is a vacationer’s dream. Stroll along Ocean Ave on the water or grill fresh seafood on the cozy porch. 420 friendly outside

Luxury Year-round Hobbit House w/ private hot tub
Fern Hollow 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.

Gorgeous Romantic Lakefront Getaway
Beautiful, 170 feet of waterfront Carriage House with a lovely sandy beach for a relaxing vacation in the Lakes Region of New Hampshire. Very close to the White Mountain National Forest, Kancamagus Highway, and several Ski Resorts. Within 45 minutes to the beaches of Maine and the Seacoast of New Hampshire. Our Carriage House is 1.5 hours from Boston and 2 hours from Worcester, MA. The Carriage House was built in 2021 with top-line finishes, fixtures, and furnishings for a romantic getaway.

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.

Historic Schoolhouse c1866 + Pool + Lake + Hot tub
Stay at our one-room Schoolhouse c1866. Winner of Maine Homes Small Space Design Award 2023 and consistently top 1-5% of Airbnb homes for exceptional hospitality, comfort, cleanliness & quintessential romantic New England vibes. The Schoolhouse is 1 of 3 homes on our family's resort-like retreat, Camp Tall Pines: Featuring tennis/pool/gym/sauna, 1000-feet of frontage along the private 80-acre Shapleigh pond (boat/swim/fish), and nestled amongst a majestic 50-acre forest of tall pine trees.

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!

The Conscious Cabin | Getaways + Retreats
Your cozy, mountain retreat awaits. Settle by the fire in this thoughtfully renovated log cabin, located in the heart of the White Mountains & less than 10 minutes from downtown North Conway's local shops, restaurants & adventures. Just 5 minutes from hiking Mt. Chocorua, paddling Lake Chocorua & exploring the scenic Kancamagus Highway. Featuring a bedroom, loft, full bathroom, kitchen, tea/coffee bar, fireplace, outdoor shower, firepit & more. Bask in the restorative magic of cabin living.

#2Marsh Views, Cozy quiet spot on river&preserve
Enjoy this 2nd floor getaway in this totally quiet & cozy spot with beautiful sunrises and awesome views off the back deck. Close to beaches and town but far enough away to be secluded from the hecticness. Lots of nature trails very close by. Roads have bike/ walking lanes. Many fresh seafood restaurants & eateries close by. Kayaks & bikes for use are available. Free parking on site. Enjoy a complimentary bottle of wine when you visit. **(Waivers must be signed for kayak & bike usage)

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!

Peaceful Cottage on Maine Flower Farm
Maine’s Peaceful 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.

Gorgeous Waterfront Home with Dock and Beach
Looking for a wonderful location to enjoy a week this summer in Maine? We have a beautiful location right on the water for you and your family to enjoy. HAVE A BOAT and want to bring it with you? We have a deep water dock. Ask us about details and cost. House is on a dead end road. Come & enjoy the Maine coast! We are located 2 miles from Portsmouth, and there are numerous activities to do in this area. Golfing, Boating, Swimming, Outlet shopping and of course the Beach!
Popular amenities for Kennebunk kayak rentals
House rentals with a kayak

Mirror Pond Cottage

Waterfront Gem walkable to Restaurants!

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

Beautiful lake-side home close to Portland Maine

Tranquil Pondside Retreat

Charming Carriage House on Historic Scenic Farm

Waterfront| Outdoor Sauna| Ski| Mountains| Firepit

Lakefront Home-Stunning Views-Hot Tub, 3100 sqft!
Cottage rentals with a kayak

Rising Tide Times - quintessential Maine cottage

Cottage on the lake! Includes kayaks & rowboat!

Lovely cottage on Sunrise Lake, Middleton, NH.

Waterfront Escape

Cozy waterfront home on Merrymeeting Bay.

Cozy Waterfront Cottage w/ Private Dock & Kayaks

Peaceful Lakeside Maine Retreat

Conway Waterfront Base for Your Family Memories!
Cabin rentals with a kayak

Idyllic Lakeside Cabin Winter Getaway

Little Lake, Big Fish - Fire Pit & Pvt Beach

Rustic Log Cabin on Pawtuckaway Lake

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

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

Get away at Crystal Lake

Private cabin with lake access, hot tub & firepit!

Bear Cabin
Quick stats about vacation rentals with a kayak in Kennebunk

Total vacation rentals
Explore 20 vacation rentals in Kennebunk

Nightly prices starting at
Kennebunk vacation rentals start at ﺩ.ﺇ 441 per night before taxes and fees

Verified guest reviews
Over 820 verified reviews to help you choose

Family-friendly vacation rentals
20 properties offer extra space & kid-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
20 of Kennebunk vacation rentals include wi-fi access

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

4.9 Average rating
Kennebunk stays are highly rated by guests—averaging 4.9 out of 5!
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- Rentals with a kayak York County
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- Sebago Lake
- Hampton Beach
- Ogunquit Beach
- Wells Beach
- Weirs Beach
- Long Sands Beach
- Popham Beach, Phippsburg
- York Harbor Beach
- Willard Beach
- Crane Beach
- Short Sands Beach
- Scarborough Beach
- North Hampton Beach
- East End Beach
- Footbridge Beach
- Popham Beach State Park
- Cape Neddick Beach
- Gooch's Beach
- King Pine Ski Area
- Gunstock Mountain Resort
- Salisbury Beach
- Hills Beach
- Crescent Beach State Park
- Jenness Beach





