Holiday houses in Drakes Island Beach

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Drakes Island Beach

Guests agree: these stays are highly rated for location, cleanliness and more.

1 of 1 pages1 / 1

Top Guest favourite

A hobbit house is nestled among lush green trees, with a sloping earth-covered roof adorned with grass and ferns. The rounded front features a large window framed in white, complemented by a natural stone border, emphasizing the home's connection with its woodland surroundings.

Earthen home in Sanford

Luxury Year-round Hobbit House w/ private hot tub

Fern Hollow 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.

4.92 out of 5 average rating, 132 reviews

Top Guest favourite

The exterior of a multi-level beach house is visible, featuring a spacious deck with railings and steps leading to the sandy area by the water. The house is painted white with green accents, and tall windows allow for natural light to enter. A brick chimney is located at one end.

Home in Wells

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

4.96 out of 5 average rating, 128 reviews

Top Guest favourite

Cottage in Wells

Brand-New 2BR Beach Retreat with marsh views

Located just a stone throw away from Wells Beach in Southern Maine, Paddle Inn is a brand-new cottage built in 2024, that blends modern design with a beachy vibe. This charming blue retreat invites you to bring your bikes and paddle boards to explore. The marsh is right in front of the cottage for your enjoyment. The second story deck offers a tranquil escape. You are close to local restaurants or enjoy local music. Explore the seacoast. Inside you will find it peaceful and relaxing.

5.0 out of 5 average rating, 77 reviews

Top Guest favourite

A contemporary cabin retreat is nestled among tall trees, softly illuminated by warm outdoor lights. A wooden deck with steps leads to a welcoming entrance. A separate sauna structure is visible, surrounded by snow-covered ground, providing a serene atmosphere in a tranquil forest setting.

Home in South Berwick

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.

5.0 out of 5 average rating, 147 reviews

Superhost

A serene view of the beach stretches before a grassy path leading to the shoreline. Waves gently lap at the sandy beach under a clear sky, where soft clouds drift above. The outdoor space is bordered by tall grass, providing a natural frame.

Home in Wells

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.

4.81 out of 5 average rating, 114 reviews

Top Guest favourite

The exterior of the A-frame cabin is showcased, featuring a unique wooden facade and metal roof. Sunlight streams through tall triangular windows, illuminating the surrounding wooded area. A gravel path leads to the entryway, enhancing the cabin's connection to nature.

Cabin in Freeport

The Maine Frame | Modern A-Frame Cabin in Freeport

• Perfect for couples, small families, or a getaway with friends, our signature A-frame features soaring ceilings, oversized windows, a cozy gas fireplace, and thoughtfully designed interiors. • This cozy 1,100-square-foot space sleeps four in two bedrooms—one King and one Queen—with a shared bathroom. • 7 minutes to downtown Freeport. • Proud to be ranked in the top 1% of eligible homes and recognized as a Guest Favorite on Airbnb.

5.0 out of 5 average rating, 155 reviews

Guest favourite

A sandy beach stretches into the distance, visible from a coastal property. The exterior features a light-colored shingle design, with a covered porch offering seating. Green shrubbery lines the foreground, creating a natural border against the ocean backdrop and clear blue sky.

Home in Wells

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 !

4.88 out of 5 average rating, 144 reviews

Guest favourite

Home in Wells

Wells Home with Ocean & Marsh Views + Beach Access

Wake up to breathtaking Atlantic Ocean sunrises and unwind with glowing salt marsh sunsets at this beautifully updated Wells beach house. Just a 5-minute walk to Wells Beach, this oceanfront retreat features panoramic water views, a brand-new porch, cedar outdoor shower, fenced yard, mini-split A/C & heat, hardwood floors, and a bright open living space designed for memorable coastal escapes.

5.0 out of 5 average rating, 10 reviews

Top Guest favourite

This quaint cottage is situated near the waterfront, featuring blue shutters and a welcoming front porch. A white picket fence borders the lush garden, while boats are visible in the marina beyond, with trees and clouds framing the tranquil scene.

Cottage in Kennebunkport

Minnow Cottage waterfront, in-town Kennebunkport

This quaint Maine cottage in the heart of Kennebunkport village is just steps from great shopping, cafes, gift shops, antiquing, fantastic dining, whale watching & sailing excursions. Perched literally over the Kennebunk River on wooden piers! You can't get any closer to the water. Take advantage of a great opportunity to stay in Dock Square in a truly unique waterfront home.

4.98 out of 5 average rating, 93 reviews

Top Guest favourite

An aerial view captures the modern cabin surrounded by lush greenery, featuring warm string lights illuminating the outdoor area. A hot tub is positioned near a cozy seating arrangement, with a gravel path visible leading away from the cabin.

Cabin in Kennebunk

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."

4.96 out of 5 average rating, 229 reviews

Superhost

Home in Wells

Ocean Views!- Across from Drake's Island Beach!

Welcome to Drakes Island! The stunning seaside community offers convenient amenities; with an affordable membership ($25/week) you can enroll your kids in day camp, use the tennis courts, and have access to the community house. Inside this 5 bedroom unit you will find plenty of space to enjoy. Fully equipped and ready for you!

5.0 out of 5 average rating, 4 reviews

Guest favourite

Home in Wells

Steps from Crescent Beach • Beach Gear Included

✔️ Deeded beach access — steps from Crescent Beach ✔️ Sleeps 10 | 4 private bedrooms + loft + 2 bathrooms ✔️ Fire pit, deck with grill + bonus loft hangout space ✔️ Beach chairs, wagon, cooler & towels all included ✔️ Dog-friendly (2 max) | Portable crib & high chair | Parking for 7

5.0 out of 5 average rating, 6 reviews