Vacation rentals in Islesboro

Find and book unique accommodations on Airbnb

Quick stats about vacation rentals in Islesboro

  • Total vacation rentals

    Explore 230 vacation rentals in Islesboro

  • Nightly prices starting at

    Islesboro vacation rentals start at G$14,642 GYD per night before taxes and fees

  • Verified guest reviews

    Over 7,340 verified reviews to help you choose

  • Family-friendly vacation rentals

    160 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 110 rentals that welcome pets

  • Rentals with dedicated workspaces

    110 properties have a dedicated workspace

  • Wi-Fi availability

    220 of Islesboro vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill, and Laptop-friendly workspace across Islesboro rentals

  • 4.9 Average rating

    Islesboro stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated vacation rentals in Islesboro

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

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Top guest favorite
A charming modern cottage with a red exterior and a pitched roof stands amidst lush greenery. The covered porch is furnished with comfortable seating, inviting relaxation. Large windows allow natural light to enter, enhancing the welcoming atmosphere of the property.
Home in Northport
4.98 out of 5 average rating, 274 reviews

Cute Midcoast Cottage w Hot Tub

Kick back and relax in this ideally located modern cottage. Enjoy a soak in the hot tub or the peace of the covered porch. Situated in the heart of midcoast Maine, this cottage has it all. An elegant kitchen that awaits your culinary delights, a spacious living area, a primary bedroom with a TV, a kingsize bed and a luxurious bath with a soaking tub and a walk-in rainfall shower, plus twin bunk beds for the kiddos. A small store and a farm to table restaurant are conveniently across the street.

LocationFamilyDecor

Top guest favorite
A charming cottage is framed by lush green trees, showcasing its light yellow exterior and welcoming front door. The grassy area surrounding the home offers a tranquil setting, and the clear sky above adds to the serene ambiance.
Guesthouse in Islesboro
4.97 out of 5 average rating, 65 reviews

Milk House

nice little cottage in Dark Harbor, near to everything. queen bed, so sleeps up to two in a quiet location for short or medium term stays. most reasonable amenities provided; hiking or social recommendations are available on request. (Wi-Fi speed excellent, though I was not able to use AirB&B's official Wi-Fi measurement option.) *Please be aware, we are on an island, which must be accessed by boat or ferry, so service can be interrupted. there's a gym at the Community Center, $10/day pass.

LocationFamilyDecor

Top guest favorite
The image captures a serene view of the water at sunset, with the sun reflecting on the surface. Framed by lush green foliage, a small rustic bench is positioned on the shore, inviting quiet moments of contemplation.
Cottage in Belfast
4.98 out of 5 average rating, 212 reviews

Quiet cottage on the bay

Settle in at this mid-coast Maine treasure, where you will find more than you hoped for in a getaway. Located in a private neighborhood and setback on a private road on 2.5 acres. You can take a short stroll down a wooded path to the Belfast bay and watch the sunset or simply enjoy the view from living room. The rocky beach gives you access to a wonderful piece of the Maine coastline. Come make some memories at this unique, pet and family-friendly quiet cottage just 1 mile to downtown Belfast.

ValueLocationParking

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
4.93 out of 5 average rating, 248 reviews

[Trending Now]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.

ValueLocationShared spaces

Superhost
Two Adirondack chairs are positioned on a grassy area in front of a small cabin with a green metal roof. Lush greenery surrounds the cabin, providing a serene and natural setting.
Guesthouse in Lincolnville
4.97 out of 5 average rating, 482 reviews

"The Lair" Guesthouse

"The Lair" is a just recently renovated small 200 square foot cabin with vaulted ceilings and plenty of natural sunlight. The building is located close to Green Tree Coffee and Tea, a coffee roaster, so the aroma of coffee will be in the air. We located about 400 yards South of the Islesboro Ferry and Lincolnville Beach and 2.4 milres North of Camden Hills State Park and Mount Battie. Free coffee from 8 am to 4 pm everyday! We are closed for Winter, will re-open Mid-April. Thank you.

ValueLocationWalkability

Top guest favorite
A charming single-story cottage is surrounded by a lush green lawn. Large windows allow for ample natural light, and flower beds with colorful blooms adorn the entrance. A serene landscape with distant hills completes the tranquil scene under a partly cloudy sky.
Cottage in Lincolnville
5.0 out of 5 average rating, 111 reviews

Sunny 2 Bedroom cottage - Walk to the beach!

Single story cottage in the heart of Midcoast Maine! This 2 bedroom cottage is in the Lincolnville Beach area. Located within eyesight and walking distance of the public beach, the Islesboro Ferry terminal, McLaughlin’s restaurant, and the Beach Store. Property is located on US route 1- just 6 miles north of Camden (8 minute drive), and less than 15 minutes south of Belfast. This year-round cottage provides a lovely retreat for resting while exploring all the Midcoast has to offer.

ValueLocationCleanliness

Top guest favorite
The cottage's exterior showcases charming architectural features, including a circular window and a cupola. A spacious deck is visible, surrounded by lush greenery and outdoor seating. The serene water views are framed by trees, enhancing the peaceful atmosphere of the Maine coastline.
Cottage in Northport
5.0 out of 5 average rating, 35 reviews

"Eagles Nest" Waterfront Cottage

Escape to our delightful waterfront cottage nestled along the rugged and breathtakingly beautiful coast of Maine. This charming and cozy retreat offers expansive water views and serene surroundings - ensuring the perfect blend of comfort and tranquility. Take in the fresh salty air, the soothing sounds of waves lapping the shore, and create lasting memories to cherish in this memorable seaside sanctuary. Book your stay with us and experience the enchanting beauty of Penobscot Bay.

LocationNearbyBathroom

Guest favorite
The Victorian cottage, painted in a soft yellow hue, is surrounded by lush greenery. A meandering pathway leads to the welcoming front porch, flanked by flowering shrubs. A white picket fence frames the yard, offering a charming entrance to the well-maintained garden.
Home in Islesboro
5.0 out of 5 average rating, 26 reviews

MASSIVE Oceanfront Dark Harbor Home on ISLESBORO

This elegant 5+ bedroom Victorian Cottage has been carefully restored and renovated to highlight the natural charm and character of the home while integrating sophisticated elements throughout. Prime location within walking distance to local coffee shop, ice cream parlor and charming gift shop. All points of island are within a 10 minute drive of the home. Massive, private bedrooms perfect for multiple couples or families. Reach out with any questions or concerns you may have!

FamilyValueAir conditioning

Top guest favorite
A screened porch offers a view of Penobscot Bay, featuring two green wicker chairs adorned with floral cushions. The scenery includes a lush lawn and Adirondack chairs positioned for relaxation, with water visible in the background and distant hills framing the horizon.
Cottage in Belfast
4.99 out of 5 average rating, 174 reviews

Spectacular Cottage on Penobscot bay in Belfast

Spectacular cottage on Penobscot bay in Belfast. The cottage is focused on the views from the great room and screened porch. You’ll love the spacious, clean, open cottage with a complete kitchen and propane fireplace. Sit on the porch with a book/glass of wine and watch for seals and schooners. Easy access to the shore along a gradual path and short boardwalk. Great amenities and comfort for vacationers both young and old. Perfect for couples and families (with kids).

FamilyLocationLayout

Top guest favorite
The treehouse structure is illuminated at dusk, highlighting its elevated design among tall trees. Soft lighting from the windows enhances its cozy appearance. A spacious deck can be seen extending from the building, inviting relaxation amidst the surrounding forest.
Treehouse in Appleton
4.97 out of 5 average rating, 454 reviews

BREEZE, in a tree The Appleton Retreat

BREEZE Treehouse, at The Appleton Retreat is located on 120 acres of private land, bordered by 1,300 acres of a protected nature conservancy. To the south is the Pettengill Stream a resource protected area and to the north a large secluded pond. BREEZE does not have a hot tub but guests may reserve the sauna, which is close by and private. The Appleton Retreat is less than a 30 minute drive to Belfast, Rockport, Camden and Rockland, charming downeast seaside towns.

LocationValueIndoor spaces

Top guest favorite
The exterior showcases a modern home featuring a metal roof and large windows. Stone steps lead to a landscaped yard filled with native plants and large boulders. A patio with seating invites relaxation while offering expansive views of the surrounding natural landscape.
Home in Northport
4.98 out of 5 average rating, 54 reviews

Cliff House - Ocean Views! Architectural designed.

Imagine a home as captivating as its landscape; one where the rolling ocean views and rising morning mist complement the allure of this particular design. A home where the floorplan has been constructed to let the natural world inside. This property is a true masterpiece; from the use of triple pane windows, private balconies, and a custom crow's nest, to the intricate masonry, 2- person hot tub (Spring, Summer, and early Fall use only), and fire pit patio.

ValueLocationHot tub

Top guest favorite
An aerial view captures the waterfront cottage nestled among lush trees along the Bagaduce River. The expansive greenery surrounds the property, leading to serene water along the shore. The distant Blue Hill mountain is visible under a clear sky, providing a tranquil backdrop for this secluded retreat.
Home in Brooksville
5.0 out of 5 average rating, 43 reviews

Casa on the Bagaduce River

Escape to this charming 2-bedroom, 2-bathroom waterfront cottage on the Bagaduce River in Brooksville, Maine. Perfect for up to 5 guests (1 king, 1 queen, 2 twins), this cozy retreat offers panoramic views of the river and Blue Hill mountain, an auxiliary wood-burning stove, claw-foot tub, modern kitchen, Wi-Fi & flat-screen TV. Enjoy relaxing on the riverfront deck. Close to nearby trails and Acadia National Park, it's an ideal spot for nature lovers.

LocationFamilyRiver

Popular amenities for Islesboro vacation rentals

When is the best time to visit Islesboro?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$43,925 GYDG$47,063 GYDG$43,925 GYDG$43,925 GYDG$38,278 GYDG$51,873 GYDG$58,148 GYDG$57,521 GYDG$51,873 GYDG$48,318 GYDG$36,604 GYDG$41,833 GYD
Avg. temp-7°C-6°C-1°C6°C13°C18°C21°C20°C16°C9°C3°C-3°C

Frequently Asked Questions

  • Are there family-friendly house rentals in Islesboro?

    Islesboro has more than 100 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in cottage rentals in Islesboro?

    Experience the best of Islesboro with our cottage rentals, starting at about $150 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly cabin rentals in Islesboro?

    Four-legged friends are welcome in Islesboro. Choose from more than 10 cabin rentals for guests traveling with pets.

  • Are there cottage rentals with a dedicated workspace in Islesboro?

    Yes! Work meets play with ease at over 10 cottage rentals in Islesboro featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do cabin rentals in Islesboro have air conditioning?

    Absolutely! We offer over 10 cabin rentals with air conditioning in Islesboro. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Islesboro have wifi?

    Absolutely! We offer over 110 house rentals with wifi in Islesboro. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Islesboro have a bbq area?

    Absolutely! We offer over 30 house rentals with a bbq area in Islesboro. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Islesboro have a gym?

    Absolutely! We offer over 40 house rentals with a gym in Islesboro. Enjoy a tailored experience with all the comforts you desire.