Vacation rentals in Kennebunk

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.

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!

Private Modern Loft featured in Maine Home+Design

“TREETOP” Experience the tranquility of staying in a PRIVATE STUDIO LOFT IN SEPARATE BLDG. overlooking 13 acres of private land abutting 600 acres of Alewive Brook Preserve ; 20 minutes to area beaches and swimming lakes. The land abuts preserve of walking trails, fishing pond, biking trails and is conveniently only 7 minutes from the highway. Immaculate with wood floors, comfy queen size bed with Tempur-pedic mattress , 400 thread count soft 100 % cotton sateen sheets and high speed Internet.

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.

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!

1760 Morrill Farm House-5 Minutes to Kennebunkport

Welcome to the 1760 Morrill Farm House, your idyllic sanctuary for your iconic Vacationland experience. Just a 5 minute drive to Kennebunk and Kennebunkport villages, Mother’s, Middle and Gooch’s beaches. Free beach pass provided. PLEASE NOTE: This unique space has very low ceilings and may not accommodate people over 6 feet tall comfortably. PLEASE NOTE: Unit 2 only has one designated parking spot. Any extra cars in your party must park on the side of the road next to the bushes.

Farmhouse Experience in a Beachside Community

2026 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.

★"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

350 Steps to Gooch’s Beach! Water Views

Ideal location 350 steps to beautiful Gooch’s beach. Easy walk or short drive to Kennebunkport's Dock Square with shops and restaurants. This is the upper floor of a 2 floor, 2 unit building. Sunny and cheerful w/open floor plan, gas fireplace, and large back deck. WiFi and live streaming tv are included. Outdoor shower. Beach chairs/towels provided. Walk to beach & town. 7 day minimum, Saturday check in/check out July through August 2026.

Romantic Mirror cabin in the woods

Stay at Hidden Pines Cabins. The Mirror cabin is Maines only 3 sided floor to ceiling mirrored glass cabin. Unwind in the hot tub while looking up at the sky full of stars. Take a sauna while surrounded by nature all around. Located in the majestic forest of mount Agamenticus, the extensive trail system is off of our road. Short drive to the Ogunquit/York beaches, Outlets at Kittery and near Portsmouth, Dover and Portland restaurant scenes.

Beautiful, spacious studio, 1 mile to beaches

Our spacious suite with private bath is comfortable, well appointed, close to everything. 1 mile to the beach. Many extras included ! The suite consists of a large studio, with private bath. The second room rents for $55 per night for a second or third person in the group and shares the bath. Free amenities include use of beach parking pass, chairs, pack-n-play, kayaks, gas grill, picnic table, fire pit

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."