
Holiday houses in Drakes Island Beach
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Top-rated holiday rentals in Drakes Island Beach
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Stunning Beachfront Home: *7/25-8/1* OPEN
One of Wells Beach's finest location. Our home provides your family with a front row beach seat to some of the best available views of Wells Beach. A Huge beach-side patio is there for family meals, sunbathing or sun drenched cocktail hour. Need a break from the sun? Right behind the beachside patio is a shaded porch for those who prefer cocktails with shade & ocean breezes. (All stays contingent on acceptance of rental agreement) Ample parking & an early 2000's updated interior. Treat yourself!

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
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.

Classic Wells Beach House
Enjoy your stay at our Wells Beach House in a perfect spot right across from the ocean. Located on a highly sought-after quiet side street with a private access walkway to the beach! This 2 story home has been completely updated with a vintage coastal design + modern amenities. Experience the Maine coast from the 2 wraparound decks where you can view the marsh and ocean with beautiful sunrises/sets. WALKING DISTANCE to 3 beaches, playground, arcade, breakfast cafes, shops, and restaurants.

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

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!

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.

Mermaid's Chair | Private Beach | Hot Tub
*Hot tub not available October - April This is a rare one. A classic 1939 Maine camp sitting directly on Casco Bay with a private dock, sweeping water views, and a saltwater hot tub, all on a quiet private road. Properties like this don't come around often, and once you're here, you'll understand why. The dock puts you right on the water, with one slip available for guests. Wolf's Neck State Park and Wolf's Neck Farm are a short walk away, and Downtown Freeport.

★"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

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.

Seacoast Escape with a View
Enjoy the peace and tranquility of staying in Kittery Maine’s exclusive waterfront area. • Walk to downtown Portsmouth • Visit Fort McClary • Hike Cutts Island Trail • Visit Crescent and Seapoint beaches • Shop and dine in Kittery’s Wallingford Square, downtown Portsmouth, and the Kittery Outlets. Everything is within fifteen minutes away! See our other home and awesome reviews: airbnb.com/h/pepperrellparadise
Popular amenities for Drakes Island Beach holiday rentals
Other great holiday rentals in Drakes Island Beach

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Riverfront Paradise-Sauna, Hot Tub & Pet Friendly!

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Beach Home w/ Exclusive privacy in Southern Maine

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Welcome to Always On My Mind -Your Wells Beach Ret

Airstream in a Forest Bath

Ocean Beach Cottage Wells, ME
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- Hampton Beach
- Sebago Lake
- Ogunquit Beach
- Wells Beach
- Weirs Beach
- Long Sands Beach
- Popham Beach, Phippsburg
- York Harbor Beach
- Crane Beach
- Scarborough Beach
- Willard Beach
- North Hampton Beach
- Short Sands Beach
- Popham Beach State Park
- East End Beach
- Good Harbor Beach
- Cape Neddick Beach
- King Pine Ski Area
- Gooch's Beach
- Footbridge Beach
- Gunstock Mountain Resort
- Wolfe's Neck Woods State Park
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