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Islesboro holiday lettings

We found 54 holiday rentals — enter your dates for availability

your current months are March, 2024 and April, 2024.
March 2024
April 2024
Discover a selection of 12 homes and other holiday rentals in Islesboro that are perfect for your trip. Whether you're staying in a holiday rental with family or friends, you'll find the amenities that you need and want, including Wi-Fi and parking. You'll be sure to find a property to rent for everyone's needs, including places that are non-smoking or accessible.

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

Find the perfect holiday rental for your Islesboro getaway

Learn about the unique charm of Islesboro with a stay in a holiday home rental. This city has something for everyone. Whether you're planning a family holiday, romantic stay or trip with friends, holiday rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Activities and attractions in and around Islesboro

Do you want to find attractions to see in the city? Venture out of your cosy holiday rental and experience everything that makes Islesboro a fun spot to go on holiday. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Samoset Resort Golf Course (14.9 mi / 24 km)
  • Owls Head State Park (15.7 mi / 25.2 km)
  • Maine State Prison Store (20.5 mi / 33 km)
  • Cellardoor Winery (8.5 mi / 13.7 km)
  • Perry's Nut House (9.9 mi / 16 km)
  • Blue Hill Books (17.6 mi / 28.3 km)

Exploring the natural features in Islesboro

Whether you're an adventurous traveller or just want to take in the scenery, Islesboro is a great place to get out in nature. These are a few of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city centre:

  • Lincolnville Beach (5 mi / 8 km)
  • Camden Hills State Park (8.2 mi / 13.3 km)
  • Barrett's Cove Public Beach (9.5 mi / 15.3 km)
  • Megunticook Lake (9.6 mi / 15.4 km)
  • Camden Harbor Park and Amphitheatre (9.6 mi / 15.4 km)
  • Mount Battie (9.6 mi / 15.5 km)

Travelling to and around Islesboro

The nearest airport is in Rockland, ME (RKD-Knox County Regional), located 18.5 mi (29.7 km) from the city centre. If you're unable to find a flight that fits your schedule, you might consider flying into Bar Harbor, ME (BHB-Hancock County - Bar Harbor), which is 29 mi (46.7 km) away.

Frequently asked questions

What is the most popular type of holiday rental accommodation in Islesboro?

Cottages are the most popular type of holiday rental in Islesboro, according to our data. Even if you've got a different idea about what you want, Vrbo has properties in loads of sizes and shapes. Explore our options to find your ideal fit.

How much does it cost to rent a holiday rental in Islesboro?

Several factors can affect what you'll pay for your holiday rental in Islesboro, like the type of property, length of stay and season. But, all our holiday homes have something in common — excellent value. Simply enter your travel dates to find your ideal match.

How much does it cost to rent a beach house in Islesboro?

Prices for beach houses in Islesboro vary depending on the type and size of the property and when you're travelling. Simply enter your travel dates into Vrbo and the number of guests to view your options and prices. From there you can use our filter tool to refine your search by nearby activities, amenities, ratings and more.

Are there pet-friendly holiday rentals in Islesboro?

With two properties that allow pets, your furry best friend can join in the fun on your Islesboro break. Use the filter tool to browse our pet-friendly holiday rentals and find a stay that's pawfect on Vrbo.

What are popular rental amenities in Islesboro?

A barbecue grill, a fireplace and a beach view head the list of most popular rental amenities in Islesboro. Whether you're taking to the road solo, with your spouse or a group of friends, Vrbo will help you find a holiday rental that fits your tastes with all the conveniences you're looking for.

Are there large group holiday rentals in Islesboro?

Yes, there are two holiday homes in Islesboro that can accommodate a group of five or more people. From family trips to a special event, these stays have ample space to chill out with the people that matter the most.

Are there holiday rentals in Islesboro that welcome kids?

Islesboro has two family-friendly holiday rentals. And discovering a stay that welcomes children is simple with our "Properties good for families" filter. On top of having the entire place to yourselves, you'll get access to perks and amenities like living rooms, full kitchens and yards.

What are the top attractions for families in Islesboro?

There's a ton of exciting things to do and see with the family in Islesboro, such as:

  • Pitcher Pond
  • Warren Island State Park
  • Schoolhouse Museum

How old do you have to be to rent a holiday rental in Islesboro?

We advise checking with the Islesboro holiday property you want on Vrbo as age restrictions vary. However, it's generally 16, 18 or 21.

How long can I rent a holiday rental in Islesboro for?

It really depends on the Islesboro property. To browse available options offering extended stays, just enter your travel dates and number of guests into Vrbo's search page. You can enjoy having the entire property to yourself, along with comforts such as a kitchen, air conditioning and a yard to run around in. Be on the lookout for long-term stays that offer weekly or monthly discounts.

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