House vacation rentals in Bailey Island

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Top-rated house rentals in Bailey Island

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Top guest favorite

An aerial view showcases the lush greenery of the property, framed by the coastline and tranquil waters of Cape Porpoise. The landscape reveals homes, docks, and boats dotting the cove, all under a bright sky with scattered clouds.

Home in Kennebunkport

4.97 out of 5 average rating, 150 reviews

Luxurious 5 bedroom on the ocean, w/ dock & kayaks

Historic 1735 home on a spacious one-acre property overlooking the ocean. Enjoy swimming from the dock in Cape Porpoise’s protected cove. Two kayaks provided for exploring the lighthouse & picnicking on nearby islands. Stroll past picturesque lobster boats to the town pier, where restaurants serve fresh local lobster & drinks. Walk to morning coffee, pastries, a local grocery store, athe renowned Nunan’s Lobster Hut. Just two miles from Kennebunkport and a nine-minute drive to Goose Rocks Beach.

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Top guest favorite

The image captures an aerial view of a serene landscape with lush green trees surrounding calm waters. The shoreline curves gently, leading to a private dock that extends into the water. A soft sunset glow reflects off the surface, creating a peaceful ambiance.

Home in Georgetown

4.99 out of 5 average rating, 139 reviews

Moss House: A Modern Waterfront Cabin in the Woods

Featured in VOGUE and Maine Home + Design, this modern, handcrafted cabin offers calm Atlantic views, 150 feet of shoreline, and a private dock, perfect for morning coffee, launching a kayak, or watching seals, seabirds, and passing boats. Set among tall pines, it blends Nordic and Japanese influences in a space that is calm and composed. Interiors of wood, stone, lime plaster, and concrete form a grounded, quietly expressive, and sustainably built retreat. 1hr from Portland, but a world apart.

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Top guest favorite

A waterfront view is captured from a deck, showcasing calm waters surrounded by a lush landscape of colorful trees. The bright blue sky reflects on the surface of the creek, while greenery provides a serene foreground.

Home in Bath

4.99 out of 5 average rating, 131 reviews

Waterfront Farmhouse with Modern Flair!

On the shores of Winnegance Creek in Bath, Maine—one of America’s best small towns—this 19th-century farmhouse has been completely renovated. Boasting waterfront views and sitting on more than an acre of land, opportunities for recreation and relaxation abound. Enjoy the outdoor deck, fire up the grill, visit the beach or the farmers market, explore the area via kayak, stargaze—so much to do! Not to mention shopping, restaurants, and all that downtown Bath and midcoast Maine have to offer!

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Guest favorite

Four wooden lounge chairs are arranged around a small table on a grassy lawn, overlooking a rocky shoreline. The calm ocean stretches into the distance, framed by a clear sky with soft clouds.

Home in Harpswell

4.93 out of 5 average rating, 162 reviews

Brand new Scandinavian cottage: dock & kayaks!

Brand new architectural cottage and detached 'boathouse' with sweeping elevated ocean views both east and west, private waterfront lawns and deep water dock with kayaks. This property was built in 2020 so expect a fresh and clean experience on one of Harpswell's most private peninsulas. Watch the sunrise from the cantilevered 2nd floor deck, sit by the campfire on your private lawn oceanside, or walk down to the dock for a paddle in the west facing protected cove. The best of coastal Maine!

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Guest favorite

Home in Naples

4.97 out of 5 average rating, 197 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!

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Guest favorite

A charming blue Victorian-style house is set on a spacious corner lot, surrounded by trees displaying autumn colors. A curved driveway leads up to the entrance, where manicured shrubs flank the walkway, enhancing the inviting façade of the home.

Home in Freeport

4.95 out of 5 average rating, 138 reviews

Freeport Escape – LLBean | Fire Pit | 3 King | A/C

The Freeport Escape – A charming early 1900s home with modern amenities. Located in the heart of Freeport, walkable to shopping, restaurants, breweries, and the Amtrak station. Set on a private corner lot, enjoy the fire pit, porch grilling, and spacious outdoor area. Cozy up by the indoor fireplace in cooler months. Perfect for families, couples, and friends. 🛏️ 3 King Beds | Family-Friendly | ❄️ A/C | 🔥 Fire Pit | 🪵 Indoor Fireplace 📍 STRR-2022-82

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Guest favorite

A serene lakeside view captures the lush greenery surrounding charming homes, including a notable waterfront structure. The calm water reflects the blue skies, while more trees line the shoreline, offering a private and tranquil atmosphere.

Home in Brunswick

4.94 out of 5 average rating, 116 reviews

Gurnet Summer Home "Beau Sejour"

Welcome to Beau Sejour. Authentic Maine property with two brand new balcony’s overhanging the ocean. Attached to the lower balcony includes a staircase- offering direct access to water/beach. A beautiful seating area and outdoor dining table rests on the upper deck, giving panoramic views of the cove and coastal wildlife. Sunrises are especially beautiful, with frequent sightings of bald eagles, osprey, and seals. An authentic Maine experience.

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Top guest favorite

The rocky coast is lined with spruce trees, showcasing natural contours along the shoreline. Calm blue waters gently lap against the rocks, while a clear sky enhances the scenic view. A few homes are nestled among the trees, blending harmoniously with the coastal landscape.

Home in Georgetown

5.0 out of 5 average rating, 128 reviews

Perched atop the Coast of the Atlantic Ocean

Enjoy sweeping vistas of the Atlantic Ocean from this 2002 home perched among spruce trees above the rocky coast. Watch for bald eagles and seals. Fall asleep to the sound of crashing waves. Walk down to the edge of the ocean to lounge or picnic. Walk 6 minutes or drive the 0.1 miles to the park entrance. Hike the Little River Trail. The house has vaulted ceilings, panoramic views, fully equipped kitchen, and whirlpool bath.

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Top guest favorite

Two Adirondack chairs are positioned on a rocky area overlooking a serene waterfront. Trees frame the scene, with the sky displaying soft hues of pink and orange during sunset. The calm water reflects the natural beauty of the surroundings.

Home in Phippsburg

4.97 out of 5 average rating, 116 reviews

Private Oceanfront Home 🔆2 min to Popham ✔️Hot Tub

Experience authentic Midcoast Maine at this private and secluded waterfront home on Atkins Bay with unobstructed views of Popham Beach State Park’s unique flood plains, rocky coast, and 12-foot tides. The house is a recently renovated 3-bed, 2-bath with a large open living space, wrap-around screened porch, hot tub, and seating area overlooking Atkins Bay. Located two minutes driving from Popham Beach, Maine’s most beautiful beach!

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Top guest favorite

A well-maintained cottage is positioned beside a tranquil body of water, surrounded by lush greenery. A spacious lawn is visible in the foreground, showcasing an outdoor seating area with a patio umbrella. The scenic view of the water complements the serene setting.

Home in Harpswell

4.98 out of 5 average rating, 240 reviews

Waterfront Cottage On Basin Cove - Amazing Sunsets

Bright, airy cottage right on Basin Cove,a tidal cove in Harpswell Maine. Cool breezes with pristine views, especially for the sunsets over the cove. At the end of Harpswell Neck, so it feels like you're far away, but still only an hour from Portland, 1/2 hour from Freeport & 15 minutes from Brunswick. Use it as your hub to explore Midcoast Maine or hunker down and enjoy the screened in porch after a swim in the cove.

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Guest favorite

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, 142 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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Top guest favorite

An open living area features a light-filled space with high ceilings and large windows. A neutral-colored sofa offers comfortable seating, complemented by a wooden dining table with stools. A contemporary refrigerator and kitchen area are visible, along with decorative elements such as a plant and a flower bouquet.

Home in Freeport

4.96 out of 5 average rating, 208 reviews

Spacious Costal Home in Freeport, ME

Come enjoy Freeport, Maine in this beautiful home. One mile from the downtown shopping district and the L.L. Bean flagship store. This two family home is being rented as a single family home, giving you the benefit of two kitchens and two living rooms. Perfect for families and groups of friends. The two sides are connected via a door similar to adjoining hotel rooms.

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