Family-friendly holiday rentals in Kennebunk

C-Howder Cabin Dog Oasis Fenced Yard

Don’t forget your dogs! Enjoy the peacefulness of this cozy tranquil cabin tucked away in the woods. The cabin has the best of both worlds; private & secluded, while being close to town. Kick your feet up on the deck. Breathe in the pine, listen to the birds & frogs. Or take a lovely stroll down Bufflehead Cove Lane, walk quietly you may see a heron or egret on the pond. Left at Port Rd. & continue down to Western Ave. Lots of stairs. Driveway very steep, requires 4-wheel drive in winter.

Birch Sea

This new, very private apartment attached to our home is in a quiet and picturesque environment minutes away from Dock Square. It's great for couples, solo adventurers and families with one child. If you are seeking to spend the day at one of the beautiful Kennebunk beaches they are just minutes away. We are committed to environmental sustainability and the apartment is powered by solar energy. A new outdoor hot tub was recently installed in February, 2024! We look forward to your visit!

Get back to nature in this new woodsy retreat.

K-port License: STR-2100303 Perfect for "leaf peeping". Beautiful 2nd floor two bedroom apartment with great light, nestled in the woods. Listen to the owls at night and wake to the birds chirping. Comfortably sleeps 5 in two queen beds and a twin XL bunk. Easy access to Goose Rocks Beach as well as Smith Preserve conservation trails for biking, hiking, trail running, snow shoeing and cross-country skiing. Located 6 miles from the center of Kennebunkport and 3 1/2 miles from Cape Porpoise.

Lower Village Lofts •North• Steps to Dock Square

The Lower Village Lofts *North* is a newly renovated large studio apartment located in the heart of the action - just steps from Dock Square (downtown Kennebunkport) and 1/2 mile to the beach! This unit features a brand new fully equipped kitchen, all new designer and higher end furnishings, and a custom built-in room divider complete with an electric fireplace, armoire, and 50" smart TV. The bedroom area has a new king bed with luxurious bedding, black out shades, and an additional smart TV.

Farmhouse Retreat Upstairs | Walk to Downtown|

Experience the charm of our beautifully renovated 1870 farmhouse, a spacious upper unit Kennebunk vacation rental, offering comfort and relaxation, just a 5-minute walk from downtown!! Enjoy easy access to local coffee shops, restaurants, the farmers market and popular Garden Street Bowling Alley. Ideal for a cozy, convenient getaway. Need more space? Check out our profile to book the full-house rental, perfect for up to 8 guests. Beach Parking Permit for Kennebunk Beaches included!!

Farmhouse Experience in a Beachside Community

2025 Summer Rentals: 7 night min requirement (Friday Check-in) / Inquire for alternative dates. Enjoy being equidistant between Dock Square and Cape Porpoise, where you be immersed in a world of top chefs, fine wines, beautiful homes, acclaimed artists, and the quintessential oceanfront charm of Kennebunkport. Relax in this inspired barn house restored design with modern touches in a farm to table community. Weather the storm with our newly installed generator.

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.

★"Life~at~Sea"★I mi to beach★W/D★Park★2 full baths

• Open floor plan/first floor bedroom+full bath • Fully stocked kitchen with coffee & tea bar • Peaceful neighborhood close to Dock Square & less than 1 mile to KBK Beaches • Shaded back+side yard/patio/grill/outdoor shower • Netflix+Sling+Hulu+HBO+Amazon Video+4 TVs • 1 car garage parking+driveway parking for 2-3 cars • washer+dryer+towels+bed linens provided • board games, pack N plays x 2 • 2 KBK beach passes+boogie boards+beach towels+chairs

Drakes Island Beach Front Breathtaking Property !

Ocean views from Kennebunkport to Cape Neddick and a gorgeous half mile sandy beach right outside your door! Watch the sunrise and the sunset over the sandy Drakes Island shores. Enjoy daily walks on the beach or take a walk on the peaceful trails nearby alongside the Rachel Carson Wildlife Refuge & Laudholm Farm, and go to town for restaurants, arcades and more fun. It doesn’t get better than this !

HotTub+Firepit/5 min to DockSquare, Dining, Beach

Follow us on IG @anchorunwind. Escape to a hidden gem nestled in the heart of the Kennebunkport area, where modern comfort meets nature's serenity. Our cabin offers an unforgettable vacation experience. ✭"...A must stay location. The host’s were very helpful and genuine..." ✭"...We’ve travelled all around the world and this is in our top 3 Airbnbs we’ve stayed in."

The Farm Loft - organic farm, 10 min to beaches

Come unwind in this upstairs apartment, tucked into the corner of our bustling organic vegetable & flower farm, Frinklepod Farm. Peruse our farm store (open May - October) for the freshest ingredients to use in your well-stocked kitchen, relax in the herb garden, and enjoy the close proximity to local beaches, trails, restaurants & shops!

Gorgeous nature views, minutes from Wells Beach

Welcome to Dragonfly Fields! All you could want from Maine and more… fields, forests, nature, beaches - and who could forget the seafood?! Dragonfly Fields has all of that and more to offer. Nestled on 12 acres of privately owned land, enjoy the peace and quiet that the home has to offer - while still not being too far off the beaten path.