Choose from 82 vacation rentals located in Islesboro, Maine. Top filters in Islesboro include Internet / Wifi, Kitchen / Kitchenette, and Parking. Prices range from $72 to $2,500 per night. Our most popular vacation rental types near Islesboro are Hotel and RV.

Top vacation rentals in Islesboro

The Apartment is above the Garage on the Right
5.0
Outstanding(70 Reviews)
Condo
 in Islesboro
Inchcliffe--Islesboro Island Waterfront Apartment
3 guests · 1 bedroom · 1 bath
Kitchen / Kitchenette · Internet / Wifi · Parking

Looking for a Condo in Islesboro, this Condo for $152 per night for your business stay, family stay, couples stay, getaway vacation, on your next trip.

$$$$
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Breathtaking ocean view from the main living area
5.0
Outstanding(74 Reviews)
House
 in Northport
Rare July weeks available!! Panoramic views from this updated oceanfront home
10 guests · 5 bedrooms · 6 baths
Garden · Kitchen / Kitchenette · Internet / Wifi

Nestled in Islesboro, this House is perfect for your next vacation. Enjoy Rare July weeks available!! Panoramic views from this updated oceanfront home 's top-rated amenities, including Dishwasher, Fireplace and Internet / Wifi, and more.

$$$$
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Stroll to the shore...
5.0
Outstanding(54 Reviews)
Condo
 in Lincolnville
Ashgrove--Farm and Gardens on the Ocean
2 guests · 1 bath
Kitchen / Kitchenette · Air conditioner · Internet / Wifi

Indulge in a peaceful retreat at Ashgrove--Farm and Gardens on the Ocean, our elegant Condo in Islesboro. Enjoy amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
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Beachfront
Property view
4.3
Excellent(100 Reviews)
Inn
 in Lincolnville
Beach Cottage Inn
Garden · Kitchen / Kitchenette · Air conditioner

Enjoy the best of Islesboro in our Inn, Beach Cottage Inn. A stunning property with amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
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Vacation rentals with internet & wifi in Islesboro

Approach to the house from the land side.
5.0
Outstanding(55 Reviews)
House
 in Islesboro
Islesboro Island Maine Oceanfront Home on 12 Private Acres
8 guests · 4 bedrooms · 3 baths
Garden · Pets allowed · Kitchen / Kitchenette

The best choice in Islesboro for House, for $214 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
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Grand and spacious cottage built in 1878!
5.0
Outstanding(56 Reviews)
House
 in Northport
Gorgeous Waterfront Estate In Historic Bayside
12 guests · 6 bedrooms · 5 baths
Garden · Pets allowed · Kitchen / Kitchenette

Looking for a business stay, family stay, couples stay, getaway vacation, or traveling to Islesboro, at $1,250 per night for your next great vacation.

$$$$
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Exterior
5.0
Outstanding(53 Reviews)
House
 in Islesboro
Island log home in Maine with ocean views
5 guests · 2 bedrooms · 1 bath
Garden · Pets allowed · Kitchen / Kitchenette

The best choice in Islesboro for House, for $135 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
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Property view
4.6
Outstanding(6 Reviews)
House
 in Northport
Hobby Hops Farmhouse
Garden · Kitchen / Kitchenette · Internet / Wifi

This House in Islesboro, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!

$$$$
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Islesboro

Islesboro travel guide

Let us help you plan your perfect Islesboro vacation. Our travel guide highlights things to do, places to see, favorite vacation rental amenities in Islesboro, and more.

Frequently asked questions

What is the price range for rentals in Islesboro?

Vacation rentals in Islesboro have a price range between $72-$2,500. The average price for rentals in Islesboro is $265 per night.

What are the top things to do in Islesboro, ME?

Islesboro, ME is a great destination for outdoor activities. From kayaking and fishing, to hiking and biking, there is something for everyone to enjoy. Here are some of the top things to do in Islesboro, ME:

  • Kayaking
  • Fishing
  • Hiking
  • Biking

What are the most popular vacation rental amenities in Islesboro, ME?

The most popular vacation rental amenities in Islesboro, ME include:

  • Beach access
  • Outdoor recreation areas
  • Fitness centers
  • Indoor and outdoor pools
  • Spas and hot tubs

Many vacation rental properties offer amenities such as private decks, fireplaces, and outdoor grilling areas. Some rentals also provide access to private beaches and boat launches. Many vacation rental properties in Islesboro, ME are pet-friendly, making them a great choice for families traveling with their furry friends.

Vacation rental properties in Islesboro, ME also offer a variety of entertainment options, such as board games, video game systems, and home theaters. The properties often come with high-speed internet access and cable TV for added convenience. Many of the rental properties also provide access to private pools, hot tubs, and fitness centers.

Where is Islesboro, ME?

Islesboro, ME is an island town located on Islesboro Island in Penobscot Bay. It is part of Waldo County and is considered a summer haven for visitors and residents alike. There are many activities to enjoy on Islesboro, such as boating, fishing, kayaking, and visiting the many historic sites.

What are the best neighborhoods to visit in Islesboro, ME?

The best neighborhoods to visit in Islesboro, ME are:

  • Seal Cove
  • Seal Harbor
  • Islesboro Village

Seal Cove is known for its historic buildings, stunning views, and great restaurants. Seal Harbor is a great spot for swimming, fishing, and boating. Islesboro Village is a great place to explore the local history and culture.

What are the popular shopping destinations in Islesboro, ME?

The popular shopping destinations in Islesboro, ME are:

  • Islesboro General Store
  • Islesboro Island Market
  • The Islesboro Ferry Gift Shop

Is Islesboro, ME safe to travel to?

Islesboro, ME is a safe place to travel to. Here are a few reasons why:
  • Low crime rate
  • Plenty of outdoor activities to enjoy
  • Beautiful scenery to explore

What is the culture like in Islesboro, ME?

Islesboro, ME is a small island off the coast of Maine that is known for its picturesque landscape and vibrant culture. Here are five aspects of the culture in Islesboro, ME:

  • A strong sense of community: Islesboro is a tight-knit community where everyone looks out for each other.
  • A focus on the outdoors: Islesboro is home to a variety of outdoor activities, from sailing and kayaking to hiking and biking.
  • A commitment to the arts: Islesboro is home to a thriving arts community, with many galleries, theaters, and music venues.
  • A commitment to sustainability: Islesboro is committed to preserving its natural environment and promoting sustainable practices.
  • A respect for tradition: Islesboro is a place where traditional values are respected and celebrated.

Where can I find affordable accommodation in Islesboro, ME?

Islesboro, ME offers plenty of affordable accommodation options. Here are four of the best:

  • Islesboro Inn – Located on Main Street, this inn offers comfortable rooms and a great breakfast.
  • Islesboro House – This affordable hotel is located on the waterfront and offers stunning views.
  • Islesboro Cottages – These cozy cottages are perfect for a family vacation and offer plenty of amenities.
  • Islesboro Motel – This motel is located near the ferry and provides comfortable and affordable rooms.

How can I get around in Islesboro, ME?

You can get around in Islesboro, ME in a few different ways:

  • By car
  • By boat
  • By bike

The island has limited public transportation, but you can rent a car, or charter a boat, to get around the island.

What are the must-visit tourist attractions in Islesboro, ME?

Islesboro, ME is a beautiful town full of interesting and unique attractions. Here are some must-see tourist attractions in Islesboro, ME:

  • The Islesboro Historical Society
  • The Islesboro Islands Trust
  • The Islesboro Ferry
  • The Islesboro Central School
Visitors can also explore the many beaches and hiking trails, and take in the stunning views of Penobscot Bay. Islesboro is a great destination for a unique and memorable vacation.

What do I need to know before visiting Islesboro, ME?

Before visiting Islesboro, ME, it's important to know a few things. Firstly, Islesboro is a small island off the coast of Maine and is only accessible by ferry. Secondly, the island is home to a variety of outdoor activities, from hiking to kayaking, so be sure to pack the right supplies. Lastly, it is important to note that the island is a quiet place, so be sure to be respectful of the locals and their way of life.

  • Islesboro is a small island off the coast of Maine and is only accessible by ferry.
  • The island is home to a variety of outdoor activities, from hiking to kayaking.
  • Be respectful of the locals and their way of life.

What are the most popular vacation rental amenities in Islesboro?

  • Internet / Wifi
  • Kitchen / Kitchenette
  • Parking

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