Holiday houses in Drakes Island Beach

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Top-rated holiday rentals in Drakes Island Beach

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

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Top Guest favourite
Home in Wells
5 out of 5 average rating, 10 reviews

Stunning Ocean Views! Renovated!

Welcome to Drakes Island! This 4 bedroom 2 bath home has stunning ocean views and was just completely renovated including: Kitchen update, completely painted, all new furniture, and more. Sit on the oversized wrap-around porch and listen to the waves crash. On the first floor you will find 2 sitting areas, dining area, well stocked kitchen, breakfast nook, full bathroom with a stand up shower, and a laundry area. Upstairs has 4 bedrooms and a full bathroom with a shower/tub combo and AIR CONDITI

Top Guest favourite
The exterior of a private entrance features a charming blue door framed by natural wood shingles. Flowering plants and greenery line the pathway, enhancing the inviting atmosphere. A trellis with climbing vines is visible beside the door, contributing to the tranquil setting.
Apartment in Kennebunk
4.99 out of 5 average rating, 177 reviews

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!

Guest favourite
A modern treehouse structure stands elevated on wooden stilts among tall trees. The building features a triangular roof, wooden shingle siding, and several large windows, allowing natural light to fill the interior. Natural surroundings create a tranquil woodland setting.
Treehouse in Sanford
4.94 out of 5 average rating, 270 reviews

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.

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
4.96 out of 5 average rating, 123 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

Guest favourite
Home in Naples
4.98 out of 5 average rating, 187 reviews

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!

Top Guest favourite
The contemporary three-story house features a light gray exterior with multiple large windows. A welcoming front porch is seen at the entrance, bordered by a neatly landscaped yard with evergreen shrubs and flowers. A paved walkway leads from the street to the front door.
Home in Scarborough
5 out of 5 average rating, 115 reviews

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.

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
5 out of 5 average rating, 127 reviews

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!

Guest favourite
Home in Wells
4.92 out of 5 average rating, 279 reviews

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.

Guest favourite
A charming white cottage is set amidst greenery, featuring a welcoming entrance with a teal door. A small porch is equipped with two outdoor chairs and a grill, offering a cozy space for relaxation. The surroundings include a grassy area and a neighboring shed.
Cottage in Ogunquit
4.94 out of 5 average rating, 132 reviews

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

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
5 out of 5 average rating, 136 reviews

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.

Guest favourite
An aerial view showcases a tiny home nestled among trees, surrounded by a gravel area. A hot tub and a fire pit with seating are visible, creating an inviting outdoor space. The wooded setting offers a serene atmosphere for outdoor relaxation.
Tiny home in Biddeford
4.96 out of 5 average rating, 239 reviews

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.

Top Guest favourite
An aerial view captures the coastal neighborhood, showcasing the home with beach access. Nearby residences are visible, alongside a street leading to the ocean. The sky displays a blend of blue hues and soft clouds, while the calming presence of the sea lies in the background.
Home in Wells
5 out of 5 average rating, 41 reviews

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.

Popular amenities for Drakes Island Beach holiday rentals

  1. Airbnb
  2. United States
  3. Maine
  4. York County
  5. Wells
  6. Drakes Island Beach