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Islesboro vacation rentals

We found 94 vacation rentals — enter your dates for availability

Discover a selection of 7 homes and other vacation rentals in Islesboro that are perfect for your trip. Whether you're staying in a vacation rental with family, friends, or just your furry companion, you'll find the amenities you need and want, which might include cable TV and a washer and dryer. What you'll find is a rental to meet everyone's needs, including places that are non-smoking or accessible.

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Find out more about Islesboro

Why visit Islesboro

  • Stunning Beaches: Islesboro is home to beautiful beaches, perfect for relaxation and family-friendly excursions.
  • Outdoor Adventures: The island offers various outdoor activities, from hiking to exploring nearby lakes and state parks.
  • Charming Accommodations: Choose from a variety of vacation rentals, including cozy cottages and spacious apartments.
  • Scenic Views: Enjoy breathtaking views of the natural beauty that surrounds Islesboro, ideal for nature lovers.
  • Local Culture: Experience the unique charm of the island through its culture and friendly community.

Popular types of accommodation in Islesboro

Discover the charm of Islesboro with a variety of vacation rentals, including private homes, cozy cottages, and spacious apartments. Whether you're searching for a convenient stay with laundry facilities or a comfortable bedroom cottage, we have options to suit every traveler's needs. Explore Islesboro's unique accommodations and find the perfect spot for your getaway.

  • Houses: The top choice among travelers to Islesboro, offering spacious and comfortable accommodations perfect for families or groups.
  • Cottages: A charming and cozy option, these quaint rentals provide a delightful retreat for a romantic getaway or a peaceful escape.
  • Apartments: Ideal for couples or solo travelers, these rentals offer convenience and a home-like atmosphere in Islesboro.
  • Cabins: A favorite for nature enthusiasts, these rustic lodgings provide a serene experience surrounded by the great outdoors.
  • Condos: A popular choice for those seeking modern amenities and proximity to local attractions in Islesboro.**

Top attractions near Islesboro

Islesboro, Maine, is a fantastic destination for outdoor enthusiasts and those seeking scenic adventures. Visitors can enjoy beautiful beaches, explore the local culture, and experience the tranquility of nature at nearby lakes and state parks. Popular attractions include Islesboro Town Beach and opportunities to explore the island itself. Whether you’re looking for relaxation or adventure, Islesboro offers a perfect getaway for every traveler.

  • Maine Maritime Academy: Located 8 miles away from Islesboro, this historic college offers a glimpse into maritime culture with its fascinating programs and rich history, providing a unique educational experience by the sea.
  • Megunticook Lake: Situated 10 miles from Islesboro, this picturesque lake is perfect for outdoor activities, featuring beautiful beaches and stunning scenery, ideal for a romantic getaway or a peaceful day in nature.
  • Camden Hills State Park: Just 8 miles from Islesboro, this national park invites adventure seekers with its hiking trails and breathtaking views, showcasing the scenic beauty of Maine's coastal landscape.

Things to do recommended for couples

Islesboro offers delightful couple experiences. Visit Cellardoor Winery for a romantic wine tasting just 9 miles away. Enjoy skiing together at Camden Snow Bowl, 12 miles away, or challenge each other at Golfer's Crossing Mini Golf, located 11 miles from the island. Adventure awaits.

Things to do recommended for families

On your family vacation to Islesboro, enjoy sweet treats at Perry's Nut House, just 10 miles away. For some family fun, visit the Oakland Park Bowling Lanes and ALLPLaY Family Entertainment Center, located 13 and 11 miles away, respectively, offering exciting adventures for all ages.

Things to do recommended for groups

Groups visiting Islesboro can enjoy a performance at Camden Harbor Park and Amphitheatre, play a round at the Samoset Resort Golf Course, or explore handcrafted furniture at Windsor Chairmakers, all while soaking in the local culture and beautiful scenery.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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

If you're traveling with a group, your family, pets, or planning an extended stay, be sure to use the appropriate filters to match your priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to Islesboro with a group: Think about how many bedrooms you'll require, as well as features like a complete kitchen or outdoor area for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Islesboro with young kids: Traveling with young kids can be quite a task. It’s important to prioritize their comfort and safety, along with amenities that suit their age, like a private swimming pool. Additionally, think about how close you are to family-friendly attractions.
  • Taking your pets with you to Islesboro: For many families, a getaway just isn't the same without their furry companion. If that resonates with you, explore Vrbo listings that welcome pets. Most pet-friendly properties offer amenities like feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Islesboro: If you're in search of vacation rentals with special offers for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include amenities like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Islesboro

Islesboro, Maine, offers a perfect blend of outdoor adventure and stunning scenery for your vacation. Explore local beaches, take in the breathtaking views, and enjoy family-friendly excursions. With its charming vacation homes and the peaceful atmosphere of Midcoast Maine, Islesboro is an ideal destination for relaxation and adventure seekers alike. Don't miss the chance to experience the island's unique charm and natural beauty during your stay.

  • Camden: Located 10 miles from Islesboro, Camden is known for its stunning coastal scenery and outdoor adventures. Nestled between the mountains and the sea, this charming city offers visitors a plethora of hiking trails that provide breathtaking views of Penobscot Bay. The local landmarks include Camden Hills State Park, where outdoor enthusiasts can explore various trails, and the picturesque harbor lined with sailboats. Golf lovers will enjoy the nearby golf courses that blend challenging play with scenic backdrops. Camden’s quaint downtown area features unique shops and delightful eateries, making it a perfect spot for relaxation after a day of adventure.
  • Rockport: Just 11 miles from Islesboro, Rockport is a hidden gem that attracts travelers seeking outdoor experiences and stunning landscapes. The city is home to several hiking trails that wind through lush greenery and lead to breathtaking views of the coast. Rockport’s proximity to Camden Hills State Park and other natural attractions makes it an ideal base for outdoor enthusiasts. Visitors can enjoy golfing at scenic courses or take a leisurely stroll along the waterfront. The charming downtown area offers a selection of local shops and restaurants, where you can savor fresh seafood while enjoying views of the harbor.
  • Belfast: Situated 10 miles from Islesboro, Belfast is a vibrant city that celebrates its coastal heritage and natural beauty. Known for its outdoor activities, visitors can explore nearby hiking trails and enjoy the serene landscapes of the surrounding national parks. The city’s waterfront is perfect for leisurely walks or picnics, while the local recreational areas provide opportunities for kayaking and fishing. Belfast’s artsy downtown is filled with unique boutiques, galleries, and eateries, making it a delightful spot to unwind after a day of exploration. The combination of adventure and culture makes Belfast a must-visit destination.

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 money on your upcoming journey? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, reserving a longer stay can lead to considerable savings. To discover a Vrbo property that aligns with your budget, feel free to use our filters to narrow down your options by price, location, and type of vacation rental. We're here to help you find the perfect fit for your needs.

Unlock savings with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on the total booking amount. Being the planner truly has its benefits. When you enroll in our travel rewards program, One Key, you’ll gain access to exclusive discounts and earn OneKeyCash on qualifying reservations. Sign up today and begin enjoying your savings.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board provides a convenient platform for you to plan new trips, keep your travel plans on track, or manage your existing bookings. Your saved or reserved properties are neatly categorized into Potential, Upcoming, or Current Trips for easy access. To check out the Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

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.

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:

  • 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)
  • Blue Hill Co-op Community Market (18.2 mi / 29.2 km)
  • Dyce Head Foot Path (7.7 mi / 12.3 km)

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:

  • 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)

Traveling 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 center. 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, Maine, United States of America when booking a vacation rental?
When considering a vacation rental in Islesboro, Maine, the area around the island's central community is an excellent choice. This neighborhood offers a charming blend of natural beauty and local culture, making it ideal for visitors looking to immerse themselves in the serene island experience.

One of the top attractions nearby is the Islesboro Historical Society, where you can learn about the island's rich history and heritage. Additionally, the picturesque beaches and hiking trails provide stunning views and opportunities for outdoor activities, great for nature lovers.

The central community area is home to a variety of properties, ranging from cozy cottages to more spacious homes, allowing for a comfortable stay regardless of your group size.
How much does it cost to rent a vacation home in Islesboro?
Prices for vacation 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 vacation 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, the areas along the eastern shore near the town center are particularly appealing. Here, travelers can find charming waterfront properties that offer stunning views of Penobscot Bay. Many of these beach houses come equipped with amenities such as spacious decks, outdoor grills, and fire pits, great for enjoying the coastal sunsets and hosting family gatherings.

The northern part of the island, near the Islesboro Island Trust's preserve, features secluded cottages located among the trees, providing a more private beach experience. These properties often include amenities like private beach access, kayaks for exploring the nearby waters, and cozy living spaces that are ideal for relaxation after a day of outdoor adventures.

In addition, the southern end of Islesboro offers a picturesque setting with properties that boast direct access to sandy beaches and nearby hiking trails. Some rentals here feature rustic charm with updated interiors, along with conveniences such as fully equipped kitchens and outdoor dining areas, allowing guests to enjoy al fresco meals while taking in the natural beauty around them.
What is the most popular type of vacation rental accomodation in Islesboro?
In Islesboro, vacation houses are the most popular type of rental, with several available across the island. These properties typically offer spacious layouts, multiple bedrooms, and well-equipped kitchens, making them ideal for families or groups. Many vacation houses also feature outdoor decks or patios, allowing guests to enjoy the stunning coastal views and natural surroundings. Cottages are another favored option, providing a charming, rustic feel that complements the island's serene atmosphere. These often come with cozy interiors and outdoor spaces for relaxation. Additionally, there are several apartments and cabins available, each presenting unique amenities tailored to different traveler needs.
Are there any family house rentals in Islesboro?
In Islesboro, Maine, there are several family-friendly house rentals available, suiting those seeking a peaceful getaway. The island offers charming homes with spacious living areas, fully equipped kitchens for family meals, and often outdoor spaces where children can play and explore. Many properties also feature amenities such as Wi-Fi and laundry facilities, ensuring a comfortable stay for families.

Visitors can enjoy the natural beauty of the area, with nearby attractions like the picturesque beaches and hiking trails, superb for outdoor adventures. The local community has an inviting space, making it an ideal destination for families looking to unwind and connect with nature.
Can I find long-stay vacation rentals in Islesboro?
A long-stay vacation rental in Islesboro is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Islesboro?
In Islesboro, travelers can find several pet-friendly house rentals that offer a unique coastal experience. Many of these properties come equipped with amenities such as spacious living areas, fully stocked kitchens, and often outdoor spaces that are great for enjoying the picturesque surroundings. Some rentals may even feature beautiful views of the ocean or easy access to private beaches, making them ideal for families or groups traveling with pets.

The island's serene environment allows for peaceful walks along the coastline, and there are also local parks and natural areas where pets can enjoy the outdoors.
Are there any remote work vacation rentals in Islesboro?
In Islesboro, Maine, there are about 12 vacation rentals suitable for remote work. This picturesque island offers a serene environment that is ideal for focusing on work while enjoying a tranquil escape. Many of these properties come equipped with essential amenities such as reliable Wi-Fi, allowing guests to stay connected with ease.

Travelers can expect comfortable living spaces with dedicated work areas, along with features like fully equipped kitchens for preparing meals. The island's natural beauty provides a great backdrop for breaks, with scenic views and outdoor spaces where one can unwind after a productive day. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Islesboro vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Islesboro with parking available—perfect for families or travelers 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 vacation rental amenities include kitchens, which allow travelers to prepare their own meals, and decks or patios for enjoying the beautiful outdoor scenery. Many properties also permit pets, suiting those who wish to bring their furry friends along. Additionally, rentals often feature coffee and tea makers for a cozy morning routine, and onsite parking is typically available for convenience.
When is the best time to visit Islesboro for a vacation rental?
The best time to visit Islesboro for a vacation rental is during the peak season from June to August, with July being the most popular month. This vibrant period draws visitors seeking to enjoy the island's natural beauty, picturesque beaches, and charming coastal atmosphere. With warm temperatures typically ranging from the mid-60s to mid-80s Fahrenheit, it's an ideal time for outdoor activities like hiking, biking, and kayaking in the serene waters surrounding the island.

During these summer months, Islesboro comes alive with tourists exploring scenic trails and soaking in the stunning ocean views. The community also hosts various local events and gatherings, allowing travelers to immerse themselves in the island's unique culture.

For those looking for a more budget-friendly option, consider visiting in November. Although it's off-peak, this month offers a tranquil ambiance, great for a peaceful retreat. You can enjoy the beautiful fall foliage and a sense of solitude that allows for reflective walks along the coast.

Ultimately, your choice will depend on whether you want an energetic summer escape filled with activities and community spirit or a quiet getaway to connect with nature in a more intimate setting.
How early should I book a Islesboro vacation rental?
Book your Islesboro vacation 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 vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Islesboro, Maine, United States of America?
In Islesboro, Maine, visitors can experience firsthand the island's natural beauty and rich history. The cozy community offers a tranquil atmosphere, great for exploring its scenic landscapes. The Islesboro Historical Society provides insights into the island's past and is a great starting point for understanding local culture.

The picturesque beaches, such as the sandy stretches at Dark Harbor, invite relaxation and family fun, while the surrounding waters are ideal for kayaking and sailing. For outdoor enthusiasts, hiking trails in the area, including those in the nearby Camden Hills State Park, offer breathtaking views of the coastline and lush forests.

Islesboro also boasts charming local shops and art galleries, particularly around the town center, where visitors can appreciate local craftsmanship and cuisine.
Can I change or cancel my Islesboro home rental booking on Vrbo?
To find Islesboro vacation 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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy cabin or a beach condo, 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 vacation 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 like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, 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 organizing 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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