Holiday rentals in Drakes Island

4.99 out of 5 average rating, 149 reviews

Flat in Kennebunk

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!

Superhost

Treehouse in Sanford

4.9 out of 5 average rating, 524 reviews

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.

4.98 out of 5 average rating, 339 reviews

Flat in Arundel

Cape Arundel Cottage 1 mile to downtown KPT

Tastefully appointed 1 bedroom apartment one mile from desirable Dock Square, Kennebunkport. This apartment features Panoramic views of the famous Cape Arundel Golf Course and Goff's Brook Tidal River. Private, secluded back deck with dining and lounge areas, Cozy furnishings throughout, King sized bed with memory foam topper, Fully Equipped Kitchen, and more! At Cape Arundel Cottage, guest experience is our highest priority! *See “other things to note” for additional important information.*

4.92 out of 5 average rating, 114 reviews

Boho Farmhouse by the Fields

Your Maine Boho Farmhouse awaits you! You’ll be tucked into the farm fields of Wells and just four miles to Drakes Island Beach. You’ll have everything you need and more at this coastal oasis. 7 miles to Wells Beach 7 miles to Kennebunk Beach 8 miles to Kennebunkport 10 miles to Ogunquit Beach Grocery stores within 4 miles: Spillers Farm Store, Wells IGA, Wells Hannaford Emergency Walk In: 2.5 miles 2 miles to closest gas station 5 miles to Wells Police Station/Wells Fire Department

4.97 out of 5 average rating, 112 reviews

Family Beach House, Wells Beach, Maine

Family Beach House on the Harbor/River of Wells Beach. House Sleeps 8 adults, plus 3 - 4 children. Full kitchen, 4 bedrooms plus Sleeping Loft, 3 baths, Dining Room, large deck, patio, laundry, outdoor shower, fire pit. Private access back beach. Bring your kayaks, paddle boards, surf boards, or boat. Water behind house at High Tide. Approx. 100 yard walk across Atlantic Ave to beach. Parking for 5 cars Max. Optional in-law apartment available, sleeps 5, for $115 per night/$800 per week

5 out of 5 average rating, 213 reviews

Cabin in South Berwick

Romantic A-Frame cabin in the woods

Modern cabin tucked privately in the forest. Loaded with modern amenities make it perfect for a romantic getaway. Unwind in the hot tub looking up at the sky full of stars. Take a Sauna while being surrounded by nature all around. Relax by the fire pit. Located in the majestic forest of mount agamenticus, the extensive trail system is off our road. Short drive to the Ogunquit/ york beaches, outlets at Kittery and near Portsmouth, Dover and Portland restaurant scenes.

4.99 out of 5 average rating, 160 reviews

Charming Wells Bunkhouse near Drakes Island Beach

This 675 sq ft bunkhouse is the perfect spot for your next beach stay! Situated on an oversized lot with plenty of parking, outdoor grill, and outdoor furniture. It has been designed and decorated with loads of Maine charm. It boasts a full kitchen, smart tv with cable and WiFi. Keyless entry will allow you to check yourself in, at your own convenience. Let me know if you need beach chairs or a cooler to complete your trip!

4.97 out of 5 average rating, 179 reviews

Flat in Wells

Bright 1 Bd w/full kitchen, quick drive to beaches

Located in the peaceful coastal town of Wells, this private suite is the perfect place to come home to after embracing all the amenities of nearby beaches, restaurants, and shops in the charming towns of Wells, Kennebunk, Kennebunkport, and Ogunquit. Sleep in comfort in your spacious king bed, enjoy a home-cooked meal in your full-sized kitchen, and relax while listening to the birds on your private deck that overlooks the garden.

4.93 out of 5 average rating, 269 reviews

Guest house in Kennebunk

Intimate Ocean View Cottage Near the Mousam River

A newly renovated 700+ sqft one-bedroom, two story cottage, with a beautiful ocean view, is less than one mile from Parson’s Beach. The Mousam River access is less than ¼ of a mile away. A cozy Maine living space with a private backyard and fire pit for your enjoyment. Interested in biking or walking trails? We are less than 500' to the bridal path that can take you to nearby Mother’s Beach or into downtown Kennebunk.

4.87 out of 5 average rating, 122 reviews

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 !

Superhost

Flat in Wells

4.83 out of 5 average rating, 321 reviews

The Crow's Nest

This is a one bedroom unit with its own private bathroom close to Wells Beach, and Route 1 Shopping, restaurants , etc. High-speed WiFi, AC/Heat, comfy queen sized bed, mini fridge, microwave, table with 2 chairs, ceiling fan, first aid kit, iron, and blow dryer. I don't do long term rentals for the summer but please message me if you'd like to do a long term rental from October to May.