Vacation 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

Skyframe 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.

Drake's Island Beach Area Studio

This studio unit at the Lighthouse Condominiums was completely remodeled, redesigned, and all furnishings and appliances are brand new for summer 2021. Walk, bike, or ride down Drake's Island Road to the beach; wander the antique shops; and dine at dozens of the best local restaurants within a 5 mile radius! How about working remotely next to the pristine outdoor swimming pool under an umbrella or in a lounge chair? Quiet, charming, & private. *2024 Update* New mattress and adjustable bed.

Seaside Escape

Relax by the ocean at this charming cottage unit located mere steps away from beautiful Crescent Beach! Swim in the ocean and then walk to & relax in your seaside, ocean view hideaway after! This one bedroom unit is located just steps from the beach, sleeps 4, and is available from May through mid October. This beautifully renovated cottage is furnished with a queen size bed in the bedroom, as well as a living room with a couch and chair that both pull out for extra sleeping space.

Higgins Beach *New* Beach Home & Private Offices

Custom designed contemporary at the beach. Perfect for a relaxing getaway, visiting family and friends or working remotely. Chef's kitchen w/ high end appliances, granite countertops, enclosed porch grill area. 3 bedrooms and 2 private offices Huge windows and amazing views from all of the rooms highlight the natural beauty of high tides, sun rises and sun sets. Wonderful beachfront walks and beautiful surroundings inside and out. Easy proximity to Portland's Old Port.

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.

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!

3-Bed | 2-Bedroom | Hot Tub | Close To Beach

If you've never stayed in Wells before, make your first stay at the oldest established property in Wells, dating back to 1604, but updated for today's modern needs with wifi, streaming, jacuzzi, grill, outdoor furniture, and hammock all within a short drive to Wells beach in a peaceful neighborhood on a dead end street. Let the Webhannet Falls and River lull you to sleep as they flow through the backyard and see the foundation of the historic gristmill and sawmill.

Cottage at Footbridge Beach Ogunquit

Our one bedroom cottage is a perfect spot to enjoy all the beach life has to offer! This charming cottage is just a few minute walk to the Footbridge and Ogunquit beach and close to many popular restaurants and bars. The bedroom has a queen size bed , tiled bathroom, cozy living area and a kitchenette with a refrigerator, microwave, toaster oven and coffee maker. Limited marsh views from the private outdoor space with room to grill and relax. All linens provided

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.

Happy Days at Wells Beach

Located directly on the marsh and just steps away from private access to a beautiful quiet section of Crescent Beach, this recently renovated and fully equipped two-bedroom, one bathroom home has everything you need for a relaxing beach getaway. Enjoy incredible views and sunsets over the Rachel Carson preserve. Half mile walk to Wells Beach center. Close to all that Wells, Ogunquit, and Kennebunkport have to offer.

The Villa of Wells

Cozy Year-Round Cottage in Wells, Maine Escape to this charming one-floor cottage, just under 5 miles to Wells Beach and 1 mile to Rachel Carson Wildlife Refuge. Enjoy a deck, full kitchen, laundry, new queen sized bed and coastal decor. Short drive to restaurants, bars, shopping, and antique shops. Perfect for a relaxing getaway in any season. Come experience the best of Wells, Maine!