
Holiday rentals with a kayak in Kennebunk
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Top-rated rentals with kayak in Kennebunk
Guests agree: these rentals with kayak are highly rated for location, cleanliness and more.

LUX Designer Private Waterfront Hot Tub - Secluded
Waterfront GLASS cabin with privacy professionally designed, escape to somewhere really special. Crooked river acres surrounding the house with the river wrapping around the property. Dock with direct access to Sebago lake and state park just minutes away, Outdoor shower, hot tub, hammocks, BIG walk-in shower w/ window. Heated bath floors, ac. See through Fireplace. The property has its own sandy swimming beach, pets are welcome. Come enjoy privacy and the space to run around seconds to Sebago.

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 Treehouse with private hot tub
Cliff House 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.

Cottage on the lake! Includes kayaks & rowboat!
Super cozy, beautiful cottage right on the lake & dirt roads. Yard: sitting areas, propane fire pit, fenced in yard. Inside includes reading areas, dvds, wifi, books, coloring books, puzzles, games. Enjoy the rowboat & kayaks or bring your own boat. We are on Antique Ally and State Parks are nearby (2 miles away). Enjoy a day at Chucksters, Concord, Portsmouth or the lakes region. Enjoy the LAKE LIFE! No animals (Health concern for cleaner) 4 adults or 2 adults 3 kids. Life jackets provided

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.

Waterfront Gem walkable to Restaurants!
Waterfront Oasis on Pettingill Pond. You couldn't get any closer to the water, it's steps away. There are 3 Kayaks, and a paddleboat, firepit and dock for guest use! This a great spot for swimming and watersports! This home has been newly renovated, the effect results in a simple, stylish, comfortable space for guests to enjoy. Walk to Franco's Bistro for from Scratch Italian food, or Bob's Seafood for a fish taco! This is a piece of paradise on sweet Pettingill Pond in the heart of Windham.

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.

#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)

☀ Fox & Loon lake house: hot tub/pedal boat/kayaks
Escape to a peaceful, lakeside retreat with a secluded sun-lit deck and private dock with incredible views of Sunrise Lake, plus a 4-person hot tub, and seasonal amenities like a pedal boat, two kayaks, a SUP board, gas fire table, central A/C, a pellet stove, and snowshoes. Enjoy nearby activities like hiking, leaf peeping, skiing, and visiting scenic towns, local vineyards and breweries — or simply relaxing in a beautiful lakefront setting. The sunsets can be unbelievable!

Birch Ledge Guesthouse--Four Season Maine Getaway
Both rustic and elegant, the Birch Ledge Guest House offers a cozy place to relax and recharge, whatever the season. The first floor features a spacious living room (with queen sized pull-out-couch), dining area, and small kitchen. The bathroom has a walk-in shower. The second floor is a loft accessible by a spiral staircase and has a comfy queen and two twin sized beds. The guesthouse is surrounded by quiet forest and is an easy 30 minute drive to Portland.

Waterfront, Wood stove & Private beach, Solo Stove
Welcome to the Luna Lake House, your very own lakefront retreat! Just 2 hrs from Boston and 1 hour from Portland, this is the perfect getaway. You get the entire house to yourself! This 1,810 sq ft house has 100 ft of private waterfront, a wood burning stove, private dock (June-October) and outdoor bonfire pit for your enjoyment. With incredible sunset views and it’s amazing location, you will make lasting memories in this one of a kind experience.

The Red Lake House
(LAKEFRONT PROPERTY) Located in a peaceful cove on Bauneg Beg Lake in North Berwick, Maine. The Red Lake House is the perfect place to relax and enjoy hot New England Summers and colorful Falls! Just a 30 minute drive to Wells Beach and 45 minutes from Portland! Your safety and comfort is our first priority so custom keyless entry codes, life jackets, and a Welcome Binder full of all the need to know info. is provided.
Popular amenities for kayak rentals in Kennebunk
House rentals with a kayak

Stunning Dock Sq Waterfront Home

Rising Tide Times - quintessential Maine cottage

Beautiful lake-side home close to Portland Maine

Charming Carriage House on Historic Scenic Farm

Old Falls Retreat-4BR w Gorgeous River View & Pool

Kennebunk Beach Retreat

Cozy Lakefront Cabin-Private Dock-Kayaks-Firepit

Tall Pines Lakeside Cottage
Cottage rentals with a kayak

“Stay Awhile in the Lake's Region”

Tranquil waterfront cottage

Little Red Lake House

Cozy camp near highland lake

20ft from the Water with Mountain View!

Loon Song Cottage on Kennebunk Pond

Serene Lakefront Retreat in Southern Maine

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

Private pond | Sebago Lake Region | Romantic

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

The Conscious Cabin | Getaways + Retreats

Harolds Camp: Lake Winnipesaukee Waterfront w/dock

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

Total holiday rentals
Explore 20 holiday rentals in Kennebunk

Nightly prices starting at
Kennebunk holiday rentals start at $90 SGD per night before taxes and fees

Verified guest reviews
Over 830 verified reviews to help you choose

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

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
20 of Kennebunk holiday rentals include wifi 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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- Hampton Beach
- Sebago Lake
- Ogunquit Beach
- Wells Beach
- Weirs Beach
- Long Sands Beach
- Scarborough Beach
- Crane Beach
- Popham Beach, Phippsburg
- York Harbor Beach
- Popham Beach State Park
- North Hampton Beach
- Willard Beach
- King Pine Ski Area
- Short Sands Beach
- Cape Neddick Beach
- Gunstock Mountain Resort
- Gooch's Beach
- East End Beach
- Funtown Splashtown USA
- Crescent Beach State Park
- Bear Brook State Park
- Pleasant Mountain Ski Area
- Footbridge Beach




