Holiday rentals in Drakes Island

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!

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.

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.

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!

1BR cozy, luxurious getaway @ Krista's Guesthouse

Newly built guesthouse above owner's garage with insane sunrises & great view. Property is located on 36 acres, owner lives on site in a separate house with her 3 dogs, 1 exceptionally lazy cat and 4 rogue chickens (they may all come visit you!). Grounds have ancient apple trees, loads of perennial gardens with more in progress, berries and an organic vegetable garden that we would love to share from if desired. Please do not hesitate to ask any questions! We hope to meet you soon!

The Maine Frame | Modern A-Frame Cabin in Freeport

• Perfect for small families or couples, our signature A-Frame cabin features a modern interior gas burning fireplace, soaring ceilings, huge windows, stylish interiors, and all the comforts of home. • This cozy 1,100 square foot space comfortably accommodates up to four guests in two bedrooms (one with a King-size bed and the other with a Queen-size bed) and a shared bathroom. • 7 minute drive to downtown Freeport. • Proud to be ranked in the top 1% and voted Guest Favorite!

★"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

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.

Private home on the beach with 360 degree views!

Directly on the beach with views of the water on both sides. This 4 bed/2 bath house has a modern feel with lots of windows and natural light. Very white, bright, and clean and can sleep up to 12 people. Amazing views and location, and it's one of a kind. The sunrises and sunsets can be seen on both sides of the home. The kitchen is stocked with everything from a microwave to a blender...you'll have what you need...and parking for 4 cars.

Tiny house near the beach!

Enjoy a wooded retreat just minutes from Maine's stunning Fortune's Rocks beach. This newly constructed tiny home welcomes you for a memorable stay near the coast. We strive to offer a thoughtful balance between modern amenities and a natural setting. This space is perfect for two guests, with a maximum of four who are comfortable sharing tiny accommodations. We are pet friendly for an additional fee - one dog maximum per reservation.

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 !

Modern A-frame w/ Mountain Views - North Conway

Welcome to our cozy 3-bedroom A-frame cabin, nestled in the heart of North Conway. Originally built by our grandparents in the 1960's, this A-frame serves as the perfect home-base for adventuring and exploring all that the White Mountains have to offer; skiing, snowshoeing, snowmobiling, hiking, biking, breweries, dining, floating the Saco, leaf-peeping and the like!