Discover a selection of 47 vacation rentals in Islesboro, ME that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including WiFi and swimming pools. Prices start at $83 per night, and houses and cottages are popular options for a stay in Islesboro. Either way, you'll find a rental for everyone's needs.
AsyncDestinationUrgency
Top rated rentals — Islesboro
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncExploreBookEnjoy
AsyncExploreBookEnjoy
AsyncExploreBookEnjoy
Destination guide

Find the perfect vacation rental for your Islesboro getaway

Learn about the unique charm of Islesboro with a stay in a private vacation home. There's no shortage of things to see and do in the area.Whether you're planning a family holiday, romantic stay or friends trip, vacation rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Things to do

Activities and attractions in and around Islesboro

Are you searching for attractions to see during your stay? Venture out of your cozy vacation rental and experience everything that makes Islesboro a one-of-a-kind vacation spot. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Camden Snow Bowl (12.4 mi / 19.9 km)
  • Owls Head State Park (15.7 mi / 25.2 km)
  • Maine State Prison Store (20.5 mi / 33 km)
  • Windsor Chairmakers (5 mi / 8 km)
  • Blue Hill Books (17.6 mi / 28.3 km)
  • Blue Hill Co-op Community Market (18.2 mi / 29.2 km)
Natural features

Exploring the natural features in Islesboro

Whether you're an outdoor enthusiast or just want to appreciate the scenery, Islesboro is a great place to get outside. Here are some of the area’s noteworthy features, all within 30 miles (48.2 km) of the city center:

  • Camden Hills State Park (8.2 mi / 13.3 km)
  • Belfast City Park (9.4 mi / 15.1 km)
  • Camden Harbor Park and Amphitheatre (9.6 mi / 15.4 km)
  • Megunticook Lake (9.6 mi / 15.4 km)
  • Mount Battie (9.6 mi / 15.5 km)
  • Laite Memorial Beach (9.7 mi / 15.6 km)
How to get there

Traveling to and around Islesboro

The nearest airport is in Bangor Intl. Airport (BGR), located 35.8 mi (57.7 km) from the city center. If you're unable to find a flight that fits your schedule, you might consider flying into Rockland, ME (RKD-Knox County Regional), which is 18.5 mi (29.7 km) away.

What are the top vacation rentals in or near Islesboro?

Whether you're looking for an intimate retreat for you and your sweetheart or someplace roomy to fit friends and family, you'll find some top vacation rentals in and around Islesboro. Here are a couple to get your inspiration flowing:

  • "Spectacular Cottage On Penobscot Bay" is popular with guests. Around 8 miles from Islesboro, it has 2 bedrooms and plenty of useful amenities, including a toaster and a firepit.
  • Alternatively, make your home away from home at "Cabin - Enjoy The Way Life Should Be - Maine Camp 484 Shore Rd". Around 5 miles from the heart of Islesboro, it has 1 bedroom and comes with air conditioning and a nearby beach.

For even more great options, use the search bar at the top of the page to find the perfect Islesboro vacation rental for you.

Can I find log cabins to rent in or near Islesboro?

Whether you're looking to book a log cabin for a romantic escape or a family adventure, Vrbo has you covered. Consider one of these vacation rentals in or near Islesboro and enjoy getting back to nature for a while:

  • "Picturesque Freedom Log Cabin: On" has all the conveniences you need for a relaxed getaway, including a kitchen and a stovetop. Once you've settled in, head outdoors and soak up the lovely scenery.
  • You won't have to give up any modern comforts if you stay at "Quintessential Maine Log Cabin Set On Gorgeous Lake". This appealing option features a fitness facility, an oven and more.

What are the top-rated vacation rentals for weekend getaways in or near Islesboro?

Get away from the hustle and bustle of everyday life at one of our weekend getaways in or near Islesboro. Whether you'd like to hang out with friends or spend time with the fam, we'll have something to suit your style. Here are a few places we think you'll love:

  • "Charming, Private Cottage On The Ocean Floor" is perfect for a weekend of enjoyment and rest. It comes with convenient amenities, such as a fireplace and a TV, and is located about 1 mile to the northeast of Islesboro.
  • Otherwise, make new memories with your favorite people at "Surrounded By Water. . . A Very Special Place", which is around 1 mile to the northeast of Islesboro. Take advantage of a water view, a barbecue grill and more here.

Can I find studio apartments for rent in and around Islesboro?

Yes, you can. If you're hunting down a small but stylish stay, you can't top a studio apartment. These compact properties ooze charm and are often situated in the heart of town. Check out the following options in or near Islesboro:

  • After a fun-filled day of urban exploration, come home to the comforts of "Cabin - Enjoy The Way Life Should Be - Maine Camp 484 Shore Rd". A stovetop and an ocean view are among the useful amenities you'll find here.
  • Another cool option is "Secluded And Rustic Island Cabin On The Bold And Rocky Penobscot Bay Coast". Don't let it's compact size fool you — this comfortable apartment is filled with handy amenities like an ocean view, a barbecue grill and much more.

Can I find short term rentals in or near Islesboro?

From simple apartments to huge vacation homes, Vrbo has your quick escape sorted. Here are just two of our favorite picks in and around Islesboro:

  • If you only need to stay a night or two, "Island Log Home In Maine With Ocean Views" is a terrific choice. It's not too far from the center of Islesboro, so you'll have easy access to all the best sights.
  • Alternatively, spend a couple of nights at "Historic Seaside Cottage With Its Own Beaches Overlooking Penobscot Bay". This centrally located property makes exploring the sights easy.

What are the best romantic weekend getaways in or near Islesboro?

Forget flowers and chocolates. Sometimes all you need is to get away for the weekend, just you and your beloved. At Vrbo, we've got romantic getaways in and around Islesboro that would make Cupid envious. Here are a few that'll sweep you off your feet:

  • Put on some soft tunes and chill together at "Spectacular Cottage On Penobscot Bay". Around 8 miles from Islesboro, this property has everything you could want for a couple's weekend away, including a fireplace and beach sun loungers.
  • Another option where you can spend a few glorious days together is "Cabin - Enjoy The Way Life Should Be - Maine Camp 484 Shore Rd". Around 5 miles from Islesboro, a fireplace and winery tours add to the ambiance here.

What are the best large group vacation rentals in or near Islesboro?

Big groups mean gigantic fun. They also mean finding a place that'll comfortably fit your entire gang. Browse our large group vacation rentals in or around Islesboro and get your loved ones together under the same roof:

  • You'll have loads of space to enjoy yourselves at "Amazing Custom Home On Private Cove With Sand Beach". Around 4 miles west of Islesboro, this generously sized property has 5 bedrooms that sleep up to 12 guests. Quality amenities include a nearby waterfront and a firepit.
  • "The Brick House In The Woods. . . Room For A Large Family" is another impressive option. It's around 16 miles to the north of Islesboro, has 4 bedrooms and sleeps up to 12 guests. A kitchen and a fireplace are among the things that'll help make your group getaway even more memorable.

What are the best houses for rent with a pool in or near Islesboro?

A pool is often a must-have when choosing where to stay on vacation, especially if you're getting away with the kids. Browse these houses with a pool in or near Islesboro and fill your days with splashing good fun:

  • Get into vacay mode at "Cliff House - Ocean Views Architectural Designed", where your biggest priority will be pool time. Amenities including a living room and coffee and tea making facilities help make this getaway a favorite with guests.
  • Spend lazy days splashing about or catching a few peaceful moments beside the water at "Holiday House For 4 Guests With 65m² In Dierhagen - 118593". This vacation home is another sought-after option and comes with books, a microwave oven and more.

Unsure how to pack your suitcase for your Islesboro break? This appealing destination has a humid continental climate. During summer, you can expect average temperatures ranging from 55 ºF to 75 ºF. Look up our selection of Islesboro vacation rentals by using the search bar at the top of the page. Simply adjust the filters to get more great ideas about where to stay.

What are the best large family vacation rentals in or near Islesboro?

The first stage of any big family trip is finding the perfect place to stay. Whether you're organizing an adventure-packed escape with the kids or an epic celebration with all your relatives, Vrbo has large family vacation rentals in and around Islesboro with plenty of space for everyone. Here are two popular options that would love to welcome you:

  • With 4 bedrooms that sleep up to 10 guests, "Surrounded By Water. . . A Very Special Place" gives you space to connect with family or friends. It's around 1 mile northeast of Islesboro and features amenities that'll keep your group content, such as nearby birdwatching activities and a dishwasher.
  • Alternatively, escape with your gang to "Cliff House - Ocean Views Architectural Designed". It's about 4 miles to the west of Islesboro, has 4 bedrooms and accommodates up to 8 guests. Handy amenities here include nearby birdwatching activities and on-site watersports.

If you're in the mood for visiting some family-friendly attractions nearby, Belfast Armistice Bridge is a great day out for young and old.

Can I find family cabin rentals in or near Islesboro?

Vacation with your kiddos in a family cabin rental in or near Islesboro and get ready to make some fantastic memories together. Here are a couple of favorites:

  • "Dream Finca In Mallorcan Style" - Enjoy fun times with your nearest and dearest at this retreat, which is around 5 miles northwest of central Islesboro. A barbecue grill and a microwave oven are among its family-friendly amenities.
  • "Secluded And Rustic Island Cabin On The Bold And Rocky Penobscot Bay Coast" - Rally the troops and spend a few nights or more at this welcoming rental, which is around 2 miles to the north of Islesboro. You'll have access to a stereo, a separate dining area and a whole lot more.

For more options, use the search bar at the top of the page and adjust the filters to find the Islesboro vacation rental that's perfect for your needs.