Waterfront vacation rentals in Islesboro

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Top-rated waterfront rentals in Islesboro

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Top guest favorite

A cozy living area is viewed through large glass sliding doors. A wooden coffee table is placed in front of a dark seating area, complemented by two plush pillows. A colorful piece of wall art adds vibrancy to the light-toned walls, enhanced by natural light from the outdoors.

Cabin in Georgetown

4.99 out of 5 average rating, 141 reviews

Sauna+Near Beach+Pond+Outdoor Shower+FirePit+A/C

Come relax at Pine Cabin, one of two cabins on 8 acres with a pond minutes from one of the best beaches in Maine. Unwind in your private outdoor cedar glass sauna w/forest views & refresh in our seasonal outside shower! * Minutes to Reid State Park & 5 Island🦞 * Fire Pit * Family Own & Run * Gas Grill * Private Bedroom w/Queen Bed * Loft w/Queen Bed & Record Player * Rain Shower * Custom cabinets & couch * Screen porch * AC/Heat * EV charger * Fast Wifi * Beach Gear * Smart TV * Generator

Top guest favorite

Home in Hampden

5 out of 5 average rating, 101 reviews

Cozy Cottage on the Penobscot — Panoramic Luxury!

Escape to your private sanctuary where tranquility meets luxury. Our Coastal Maine Cottage home is perched on a granite ledge that disappears twice daily with the rising tide. Enjoy the pristine interior bathed in natural light, cherry floors, and gourmet kitchen. Wake to panoramic views of the Penobscot River from the owner's suite. Conveniently located 12 minutes to downtown Bangor, our retreat offers easy access to urban amenities, an international airport, and Acadia! IG @cozycottageinmaine.

Superhost

A contemporary house is positioned near the shoreline, surrounded by trees with autumn foliage. A stone wall borders the beach, providing a clear separation from the water. The house features multiple windows and a porch, with a fire pit area on the lawn visible in front.

Home in Trenton

4.93 out of 5 average rating, 287 reviews

Acadia National Park ocean front & garden cottages

Both our houses are designed in the contemporary style. We used custom made decor and cherry tree furniture. A lot of windows, glass doors, bright and open space are inside the house. It is very quiet outside. You most likely will be alone at the beach. We share the whole sea cove with only one neighboring house. It is a pure paradise if you want to live on the beach on your own and within minutes of driving to the main local attractions. You'll be amazed of our botanical garden and landscape.

Top guest favorite

A serene deck area features two wooden chairs and a small table overlooking a lush green lawn and tranquil water. The peaceful view includes trees framing the shoreline, offering a calming ambiance and connection to nature.

Home in Belfast

4.96 out of 5 average rating, 130 reviews

Belfast City Park Ocean House

Welcome to an exquisite retreat nestled on a tranquil dead-end lane in the thriving coastal City of Belfast. With private access to Belfast City Park and Ocean, this charming space offers unparalleled serenity, boasting breathtaking views of Penobscot Bay and beyond. The meticulously manicured grounds offer an ideal setting for relaxation and outdoor entertaining, with the added allure of explorations along the shoreline or tennis/pickleball courts at park/year round hot tub. No parties.

Guest favorite

The exterior of a coastal cottage is visible, surrounded by green grass and a gravel pathway. A wooden fence frames the property, with a bush nearby. The backdrop features a tranquil body of water under a clear blue sky.

Home in Deer Isle

4.92 out of 5 average rating, 38 reviews

Lupine Landing

At Lupine Landing, you'll find your dream coastal Maine getaway. This secluded cottage is situated on 13 acres and has over 800 feet of oceanfront to explore. There is boat house on the water's edge supplied with kayaks, an outdoor shower, and many wonderful spots to swim or soak up the sun. The house has a wood stove for chilly evenings, and well equipped kitchen. The villages of Deer Isle and Blue Hill are close by, where you'll find shops, restaurants, and great local businesses.

Top guest favorite

A houseboat floats gently on the calm waters of Lake Pemaquid, surrounded by lush greenery on the hillsides. The vessel features large windows, a spacious deck, and a vibrant red and cream exterior, reflecting the tranquil ambiance of the natural setting.

Houseboat in Bremen

5 out of 5 average rating, 108 reviews

Houseboat ROAM on Lake Pemaquid, Mid Coast Maine

- A Little Closer To Nowhere - A one-of-a-kind eco-travel experience, ROAM is a simple - but comfortably equipped - houseboat that can accommodate two guests. Homeported on Lake Pemaquid in Bremen, Maine, you will seamlessly integrate into your surroundings while enjoying visiting loons, sweeping sunsets, and clear northern air. ROAM (& her brother NOMAD) are offered in conjunction with the exclusive Otyokwa Lakeside Cabins - please inquire if you'd like to add a land option!

Guest favorite

A spacious white tipi is nestled among trees, with a clear view of a quiet lake. A picnic table sits nearby, accompanied by a hammock stretched between two trees, inviting relaxation in this serene natural setting.

Tent in Brooks

4.91 out of 5 average rating, 221 reviews

Waterfront Tipi Glamping // Phoenix Landing

Majestic private waterfront Tipi * on a lake. Quiet nature oasis with hot tub, woodstove, firepit, modern grill, and all the essentials. Ice skate or xc-ski across the frozen lake and watch the bald eagles fly overhead, or relax in the Adirondack chairs in front of the bonfire while you make smores and cook dinner on the grill or over the open fire, then snuggle up inside the tipi while you listen to vintage vinyl and let the owls hoot you to sleep. *Tipi closed March-April.

Guest favorite

A small guest house is set amidst lush greenery, featuring a dark exterior with large windows. A bright green door provides a striking contrast. The surrounding trees and plants contribute to a natural, secluded atmosphere that emphasizes privacy.

Guesthouse in Sedgwick

4.95 out of 5 average rating, 282 reviews

Tiny house with AC!!

A tiny guest house (450 sq ft) overlooking the Benjamin River. AC!!. Enjoy a cup of coffee on your private porch. Living area has a smart tv (no cable, but internet available to access your streaming account). DVD's also available. Kitchenette comes with Keurig with k-cups included, mini fridge, coffee maker/filters, toaster oven, microwave, 2 burner hot plate (no oven), dishes/pots and pans. There is a loft with an army cot. Not suitable for children under age 5.

Guest favorite

An open-concept great room features high wooden ceilings with exposed beams. Large windows provide ample natural light and views of the surroundings. A comfortable seating area includes a sofa and coffee table, while a dining space with chairs is positioned near the kitchen.

Cottage in South Thomaston

4.95 out of 5 average rating, 173 reviews

Timeless Tides Cottage

This comfortable 2 bedroom, one bathroom, A-frame pine cottage is set on its own private point with 350 feet of waterfront! Cook out on the grill, lounge on the deck or dock while taking in the wildlife on a beautiful tidal river. Watch nesting Bald Eagles and Great Blue Herons fishing! There is plenty of sight-seeing in this picturesque area. Rockland is just 10-minutes away where you can enjoy shopping, restaurants, museums, galleries, lighthouses and festivals.

Top guest favorite

A screened-in porch features a set of white wicker furniture with blue-striped cushions and decorative pillows. A glass table sits at the center, surrounded by armchairs. Sunlight filters through the surrounding screens, highlighting the natural wood flooring.

Cottage in Islesboro

5 out of 5 average rating, 28 reviews

"The Dory" on Penobscot Bay, Mid-Coast Maine

Looking over Penobscot Bay, "The Dory" is a perfect place to relax and enjoy island life. Set on a dead end street in a quite neighborhood it is easy to connect with nature either in the hammock, on the lawn or on the beach. The screened in porch has a great view of the bay to watch the sunrise or sunset. We can put you in touch with a local fisherman for some fresh lobster or mussels.

Top guest favorite

A vibrant sunset casts hues of pink and orange across the sky, reflecting on the calm waters of West Penobscot Bay. Silhouetted trees frame the picturesque scene, creating a serene coastal atmosphere. The shoreline gently meets the water, enhancing the tranquil setting.

Guesthouse in Islesboro

5 out of 5 average rating, 10 reviews

Islesboro Island Oceanfront Cottage

Take it easy at this unique and tranquil getaway. This cottage is on the Island of Islesboro, accessed by car ferry from Lincolnville, private plane, or private boat. Located at the end of a mile long, private road, this guest house situated right on the shorefront on West Penobscot Bay. Watch sailboats and eagles from the front porch. Fall asleep to the sound of the waves.

Top guest favorite

The cottage exterior features a combination of stone and shingle siding, with large windows reflecting the warm colors of the sunset. A covered porch area is accentuated by wooden benches, while carefully maintained landscaping surrounds the entrance.

Cottage in Lincolnville

4.95 out of 5 average rating, 42 reviews

Seafront Cottage with private beach

Private and spacious 3-bed, 2 bath cottage situated on a quintessential piece of Lincolnville seafront; 15 acres of beautiful and well-maintained land, meandering down to private beach. The homes two-level layout is perfect for a small family or group of friends. Close to Lincolnville Beach and Camden.