Photo by Colleen Johnson

Islesboro holiday lettings

We found 79 holiday rentals — enter your dates for availability

Discover a selection of 8 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.

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Why visit Islesboro

  • Stunning Natural Beauty: Islesboro boasts picturesque beaches and tranquil lakes, perfect for relaxation and exploration.
  • Outdoor Adventures: Enjoy a variety of activities in nearby state parks, ideal for hiking, kayaking, and family outings.
  • Charming Accommodation: Choose from delightful private vacation homes, quaint cottages, and spacious apartments for a memorable stay.
  • Rich Cultural Experience: Discover the local culture through quaint downtown areas and scenic surroundings.
  • Proximity to Myrtle Beach: Experience both relaxation and adventure with stunning coastal vistas just a short distance away.

Popular types of accommodation in Islesboro

If you're pondering what type of accommodation to choose in Islesboro, worry not, as we have it all sorted for you. Our most sought-after options include houses, charming cottages, and spacious apartments. Whether you're searching for cosy house rentals or convenient vacation rentals, we’re here to provide you with all the relevant information on Islesboro hotels and holiday homes to ensure a delightful stay.

  • Houses: The top choice for visitors to Islesboro, offering spacious and comfortable settings ideal for families or groups.
  • Cottages: A delightful option for those seeking a quaint and homely atmosphere, perfect for a relaxing getaway.
  • Apartments: A practical selection that provides the convenience of self-catering in a more urban setting.
  • Cabins: These rustic retreats are perfect for those wanting to immerse themselves in nature.
  • Chalets: A charming choice that combines comfort with a touch of alpine style, ideal for a unique experience.**

Top attractions near Islesboro

Islesboro, Maine, is a delightful destination for outdoor enthusiasts and those seeking stunning scenery. Visitors can explore beautiful beaches, tranquil lakes, and nearby state parks, perfect for a variety of activities. The area offers a rich cultural experience alongside ample opportunities for adventure, making it an ideal spot for families, couples, or solo travellers looking to unwind and enjoy nature.

  • Maine Maritime Academy: A historic institution located 5.0km from Islesboro, offering a glimpse into maritime culture and education. Explore its fascinating maritime heritage and enjoy the vibrant atmosphere.
  • Megunticook Lake: Situated 6.2km away, this picturesque lake is perfect for outdoor activities. With its beautiful beaches and stunning scenery, it provides a romantic setting for relaxation and adventure.
  • Camden Hills State Park: Just 5.0km from Islesboro, this national park features breathtaking views and various trails for hiking enthusiasts, making it an ideal spot for outdoor adventures.

Things to do recommended for couples

Islesboro offers delightful romantic experiences for couples. Visit Cellardoor Winery for a charming afternoon of wine tasting, or enjoy a fun round at Golfer's Crossing Mini Golf. Don't forget to dine at Stonington Sea Products, where you can relish delicious seafood in a warm, inviting atmosphere.

Things to do recommended for families

During your family vacation in Islesboro, enjoy delightful treats at Perry's Nut House, embark on an adventure at Oakland Park Bowling Lanes, and have a fantastic time at the ALLPLaY Family Entertainment Center, all within a short drive from your base in Islesboro.

Things to do recommended for groups

Experience the vibrant atmosphere at Camden Harbor Park and Amphitheatre, only 6.2km from Islesboro. Alternatively, explore unique crafts at Windsor Chairmakers, 3.1km away, or challenge your mates to a round of golf at the scenic Samoset Resort Golf Course, located 13.1km from the island.

What do I need to keep in mind when booking a vacation in 'Islesboro

If you’re travelling with a group, family, or pets, or if you’re seeking longer stays, be sure to filter according to your key priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to Islesboro with a group: Take into account the number of bedrooms required, along with features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily refine your search on Vrbo to include all these options and more.
  • Traveling to Islesboro with young kids: Travelling with young children can present its challenges. It's important to prioritise their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Islesboro: For many, a family holiday isn’t truly complete without their furry companion. If this resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that everyone feels at home.
  • Planning for a long term stay visiting Islesboro: If you're in search of holiday rentals with discounts for stays of a month or more, you've come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. Don't forget to include extras like a parking space, a well-equipped kitchen, or even a private pool in your search criteria.

Where to stay near Islesboro

Islesboro, Maine, offers a delightful escape for those seeking adventure and natural beauty. Nestled in Midcoast Maine, this charming island is perfect for outdoor enthusiasts and families alike. Explore the picturesque surroundings, including scenic beaches and quaint downtown areas, while indulging in leisurely excursions. Nearby, discover delightful destinations like Myrtle Beach, where you can enjoy a blend of relaxation and adventure amidst stunning coastal vistas.

  • Lincolnville: Located 3.1km from Islesboro, Lincolnville is a gem for outdoor enthusiasts and adventure seekers. This charming city offers stunning scenery with its picturesque hiking trails and well-maintained golf courses. Visitors can explore the nearby national parks, where you can hike amidst lush landscapes or relax by tranquil lakes. The area is perfect for those who appreciate the beauty of nature and wish to engage in a variety of outdoor activities.
  • Belfast: Situated 6.2km from Islesboro, Belfast is a vibrant city that beckons with its scenic views and recreational opportunities. The city is well-known for its extensive hiking trails and inviting parks, making it an ideal spot for those looking to immerse themselves in the great outdoors. Visitors can enjoy the local educational centres and recreational areas, as well as nearby national parks and lakes that provide a perfect backdrop for a day of exploration and relaxation.
  • Rockport: Located 6.8km away from Islesboro, Rockport is another delightful destination for nature lovers and adventure enthusiasts. This city is famed for its hiking trails and excellent golf courses, which attract visitors eager to enjoy the outdoors. The proximity to national parks and stunning lakes offers ample opportunities for exploration. Rockport’s charming landscape and vibrant community make it a wonderful place to unwind and experience the beauty of the Maine coast.

Best time to go to Islesboro

If you're planning a trip to Islesboro, it's a good idea to check both the weather and property rates. The warmest months are July and August. Peak season runs from June to August, while off-peak times, like November to January tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January26.1°F (-3.3°C)Light RainMostly CloudyModerately LowSlightly Low
February26.8°F (-2.9°C)Light RainMostly CloudyAverageAverage
March33.1°F (0.6°C)Light RainMostly CloudyAverageSlightly Low
April42.4°F (5.8°C)Light RainMostly CloudyAverageSlightly Low
May51.8°F (11.0°C)Light RainMostly SunnyAverageAverage
June59.2°F (15.1°C)Light RainMostly SunnyModerately HighSlightly High
July65.8°F (18.8°C)Light RainMostly SunnyModerately HighSlightly High
August65.8°F (18.8°C)Light RainMostly SunnyModerately HighSlightly High
September60.1°F (15.6°C)Light RainMostly SunnyAverageAverage
October51.4°F (10.8°C)Light RainMostly SunnyAverageAverage
November41.2°F (5.1°C)Light RainMostly SunnyModerately LowAverage
December32.5°F (0.3°C)Light RainMostly CloudyModerately LowAverage

Booking with Vrbo is simple

Are you hoping to save on your next getaway? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, consider the potential savings of booking a longer stay. To discover a Vrbo property that suits your budget, utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Effortless planning

Vrbo's ingenious Trip Board offers you a convenient way to plan new adventures, pick up from where you last stopped, or manage and review your travel arrangements. You can easily locate the properties you've saved or booked under Potential, Upcoming, or Current Trips. To make the most of Trip Boards, simply visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

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)
  • Stonington Sea Products (15.1 mi / 24.3 km)
  • Maine State Prison Store (20.5 mi / 33 km)
  • Dyce Head Foot Path (7.7 mi / 12.3 km)
  • Castline Golf Club (8.5 mi / 13.6 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)
  • Belfast City Park (9.4 mi / 15.1 km)
  • Camden Harbor Park and Amphitheatre (9.6 mi / 15.4 km)
  • Mount Battie (9.6 mi / 15.5 km)
  • Rockport Marine Park (11.1 mi / 17.9 km)
  • Rockland Harbor Park (16.6 mi / 26.7 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 best area to stay in Islesboro when booking a holiday rental?
When considering the best area to stay in Islesboro, Maine, for a holiday rental, the community of North Islesboro is particularly appealing. This area offers a serene atmosphere, making it ideal for those seeking a peaceful getaway. North Islesboro boasts an array of charming properties, with many located near the coastline, providing stunning views of the water.

One of the top attractions in North Islesboro is the beautiful Sandy Point Beach, superb for leisurely strolls or picnics. The beach's tranquil waters are also great for swimming during the warmer months. Additionally, the Islesboro Historical Society is a must-visit for those interested in the local heritage, showcasing fascinating exhibits about the island's past.

With a variety of properties available, from quaint cottages to larger homes, North Islesboro offers something for everyone, ensuring a memorable stay in this picturesque part of Maine.
How much does it cost to rent a holiday home in Islesboro?
Prices for holiday rentals in Islesboro vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Islesboro to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Islesboro holiday house rentals?
You can find great discounts on house rentals in Islesboro on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Islesboro?
For renting a beach house in Islesboro, consider the picturesque waterfront properties along the eastern shore, particularly near the village of Islesboro itself. This area offers charming cottages and larger houses with stunning views of Penobscot Bay. Many of these rentals come with amenities such as private docks, outdoor seating areas, and fully equipped kitchens, making them great for families or groups looking to enjoy a seaside getaway.

Another appealing option is the area near the ferry terminal, where you can find beach houses that provide convenient access to local shops and restaurants. These properties often feature spacious living areas and outdoor decks, ideal for soaking up the coastal atmosphere.

Additionally, the northern part of the island, close to the scenic trails of the Islesboro Island Trust, offers a more tranquil setting with beach houses surrounded by nature. Many of these rentals include amenities like fire pits, grills, and easy access to secluded beaches, great for those wanting to explore the island's natural beauty.
What is the most popular type of holiday rental accomodation in Islesboro?
In Islesboro, holiday houses are the most popular type of holiday rental, with about 28 available across the island. These properties often feature spacious layouts, multiple bedrooms, fully equipped kitchens, and outdoor areas—ideal for enjoying the stunning coastal views. Additionally, there are several apartments, cottages, and cabins that provide alternative options for travellers seeking a more intimate or rustic experience. Many of these rentals are situated near the waterfront, offering easy access to the island's beautiful beaches and scenic walking trails.
Are there any family house rentals in Islesboro?
In Islesboro, Maine, there are several family-friendly house rentals available, making it a wonderful spot for gatherings. The island offers a tranquil atmosphere with beautiful coastal views, great for reconnecting with loved ones. Many of these homes feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces where children can play safely.

Visitors can also enjoy nearby attractions like the picturesque beaches and nature trails, providing opportunities for outdoor activities such as hiking and swimming. The local community is known for its charming character, with quaint shops and eateries that reflect the island's unique culture.
Can I find long-stay holiday rentals in Islesboro?
A long-stay holiday rental in Islesboro is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Islesboro?
In Islesboro, there are several pet-friendly house rentals available, providing a wonderful option for travellers looking to enjoy a getaway with their furry companions. Many of these holiday homes feature amenities such as spacious living areas, well-equipped kitchens, and outdoor spaces like decks or gardens, superb for relaxing after a day of exploration.

The island is known for its serene beauty and offers easy access to pet-friendly beaches where your dog can enjoy the sand and surf. Additionally, there are picturesque walking trails and parks in the area that welcome pets, allowing for enjoyable outings amid the stunning Maine landscape.
Are there any remote work holiday rentals in Islesboro?
In Islesboro, Maine, there are a variety of remote work holiday rentals available, with around 48 properties suiting those needing a productive environment. This picturesque island offers a tranquil setting for remote workers, surrounded by stunning coastal views and natural beauty. Many of the rentals feature amenities such as high-speed internet and free Wi-Fi in-room, ensuring that you can stay connected while enjoying the serene surroundings.

The island is known for its charming coastal landscape, with opportunities for outdoor activities such as hiking and exploring the local beaches. Properties often come equipped with comfortable workspaces, spacious living areas, and well-equipped kitchens, allowing for a balanced blend of work and leisure. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Islesboro holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Islesboro with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Islesboro?
In Islesboro, popular holiday rental amenities include kitchens, allowing guests to prepare their own meals, and decks or patios for enjoying the stunning surroundings. Many properties are pet-friendly, making it easier for travellers to bring their furry companions along. Additionally, rentals typically provide coffee and tea makers for a warm beverage at any time, as well as onsite parking for convenience.
When is the best time to visit Islesboro for a holiday rental?
The best time to visit Islesboro for a holiday rental is during the peak season from June to August, with July being the most popular month. This lively period attracts families and outdoor enthusiasts looking to enjoy the stunning coastal scenery and warm weather. Visitors can indulge in activities like kayaking, sailing, and hiking, all while soaking up the sun on beautiful beaches.

During these summer months, temperatures typically range from 15 to 25 degrees Celsius, creating ideal conditions for outdoor exploration and seaside relaxation. The vibrant setting of Islesboro during this time is complemented by community events and local markets, offering a taste of the unique culture the island has to offer.

For those seeking a quieter experience and more budget-friendly options, consider visiting in November. This off-peak month presents a serene landscape, superb for peaceful walks along the shore and enjoying the tranquillity of the island without the crowds. The crisp autumn air can be invigorating, making it a lovely time to reflect and recharge.
How early should I book a Islesboro holiday rental?
Book your Islesboro holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Islesboro?
In Islesboro, Maine, visitors can enjoy a tranquil escape with a variety of attractions that highlight the island's natural beauty and rich history. The island is known for its stunning coastal views and serene beaches, making places like Dark Harbor and the sandy shores at the north end popular spots for relaxation and swimming.

The Islesboro Historical Society provides insights into the island's past, showcasing exhibits that reflect the local culture and heritage. For those who appreciate nature, the scenic trails at the Islesboro Island Trust offer opportunities for hiking and exploring the island's diverse ecosystems.

Additionally, the picturesque views from the Islesboro ferry terminal are a treat for photography enthusiasts.
Can I change or cancel my Islesboro home rental booking on Vrbo?
To find Islesboro holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Islesboro holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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