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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Guest favourite
A welcoming entryway features a light gray console table with a decorative bowl and figurines displayed atop it. A round mirror adorns the wall above the table. The staircase, with wooden handrails and white steps, leads to the upper levels. Neutral tile flooring completes the space.
Townhouse in Wells
4.97 out of 5 average rating, 34 reviews

Four Story Townhouse With Ocean View 55

Our newly re-done townhouse is available year-round featuring a beautiful kitchen/living area with gas fireplace and relaxing balconies. This townhouse is equipped with gas heat, central air conditioning, ceiling fans, a fully equipped kitchen with a dishwasher, a gas grill, cable TV, Wi-Fi, and more! The 3-bedroom townhouses come with an additional Bedroom on the 4th floor. Feature 2-1/2 bathrooms and a washer and dryer. Private parking for 2 vehicles. Pools/hot tub are shared with community.

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Top Guest favourite
Home in Wells
4.95 out of 5 average rating, 197 reviews

Immaculate Moody Beach House

Steps from private Moody Beach, this stunning 3-level coastal home sleeps 12 and offers ocean views on one side and marsh views on the other. Enjoy 5 bedrooms, 10 private decks, a giant party deck overlooking Rachel Carson Wildlife Refuge, billiard room, fireplaces for cozy nights in, and a huge open living space with gourmet kitchen and wraparound sofa. Private parking for 6 cars. Perfect year-round getaway close to Ogunquit, York Wild Kingdom, Kittery shopping outlets, and Kennebunkport.

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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, 128 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

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Top Guest favourite
An aerial view displays a colonial home surrounded by vibrant autumn foliage, set on an expansive lawn. The nearby Kennebunk River curves through the landscape, bordered by trees. The property includes a serene setting with open spaces and distant houses visible among the greenery.
Home in Arundel
4.95 out of 5 average rating, 109 reviews

Classic, calm river view & centrally located home

We are happy to share with you our coastal, colonial home set on eight acres along the Kennebunk River. Enjoy our quaint, warm home just 5 min to the beach and 3 minutes to Cape Arundel Golf Club. Our 4 bdrm, 2.5 bathroom suits short or long term stays. The location is ideal: 6 min from Kennebunkport, 15 min from Biddeford, and 30 min from Portland or Portsmouth! We hope to make you feel at home with the morning birds chirping and the calmness of the river just in back of the property.

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Top Guest favourite
The exterior of a brand-new blue cottage is displayed, featuring multiple stories and expansive windows. A small seating area with a white chair and potted flowers is positioned on the greenery in front. The serene landscape includes the nearby marsh and water views.
Cottage in Wells
5.0 out of 5 average rating, 74 reviews

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.

LocationFamilyAccuracy

Top Guest favourite
A spacious living area features a large, white, slipcovered sectional sofa adorned with decorative pillows. A light wooden coffee table sits in the center, highlighted by a small potted plant. Artwork adorns the walls, and soft lighting creates a bright, inviting atmosphere.
Home in Kennebunk
4.97 out of 5 average rating, 373 reviews

★"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

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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
4.81 out of 5 average rating, 114 reviews

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.

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Guest favourite
A charming beach cottage features a stone exterior and a welcoming front porch surrounded by a white railing. The spacious deck is equipped with seating, inviting relaxation. A sunlit sky complements the serene coastal setting, with nearby homes visible to the left and right.
Home in Wells
4.84 out of 5 average rating, 38 reviews

Charming Beach Front Cottage

Step into our cozy beach cottage nestled right on the sandy shores. Situated on a serene stretch of Wells Beach, tranquility reigns with no public parking to disrupt your peace. Wander to the arcade, shops, and eateries—all within easy strolling distance. No worries about parking, our home can park 3 cars. Enjoy the beautiful morning sunrises! With room for up to six guests, your seaside retreat awaits!

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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
4.88 out of 5 average rating, 143 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 !

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Guest favourite
Home in Wells
4.91 out of 5 average rating, 11 reviews

Family-Friendly Coastal Home | Walk to Moody Beach

Welcome to your perfect getaway on Moody Beach! Nestled just 0.02 miles from the exclusive Moody Beach on the Southern Coast of Maine, Shorehaven Retreat offers the perfect blend of modern comfort and coastal charm. Inside, you’ll find a spacious, open layout that seamlessly connects the living and dining areas, creating an inviting atmosphere for both relaxation and social gatherings.

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Top Guest favourite
The cabin is illuminated warmly at dusk, featuring a hot tub in the backyard. Outdoor seating arrangements with four chairs are positioned around a fire pit, set against a backdrop of trees, creating a serene and inviting atmosphere.
Cabin in Kennebunk
4.97 out of 5 average rating, 245 reviews

HotTub/5min to K-port, Pet friendly, @anchorunwind

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."

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Superhost
Home in Wells
5.0 out of 5 average rating, 4 reviews

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!

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Popular amenities for Drakes Island Beach holiday rentals