Discover Your Perfect Islesboro Vacation Homes

Islesboro Pet Friendly Vacation Rentals

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9.5 (19 Reviews)
House
Point Lookout
  • Pet Friendly
  • Balcony/Terrace
  • Security/Safety
View Availability
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Why Choose Rent By Owner for your Islesboro Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Islesboro

When should you plan your Vacation Rentals stay?

Choosing the optimal time to visit can enhance your experience here, as the best seasons for enjoying the area’s natural beauty and tranquil atmosphere often depend on your preferred activities and weather conditions.

Peak Season Highlights

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June to August

During the summer months, this destination experiences its highest influx of visitors seeking warm weather and outdoor activities. Booking your vacation rental in advance ensures you secure a desirable property amidst the busy season.

Average Temperature Daytime: 75-85°F - Nighttime: 55-65°F
spring
September to October

Early fall offers pleasant weather and vibrant foliage, attracting travelers looking for scenic views and outdoor exploration. The region’s natural beauty peaks during this time, making it an ideal period for your stay.

Average Temperature Daytime: 65-75°F - Nighttime: 45-55°F

Off-Season Highlights

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November to April

This time of year sees fewer visitors, offering a peaceful retreat with tranquility and lower rental prices. It’s perfect for those wanting to experience the area’s serene charm without the crowds.

Average Temperature Daytime: 30-45°F - Nighttime: 20-30°F
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May

Spring gradually awakens here with mild temperatures and blooming landscapes. While less crowded, it provides an excellent opportunity for early-season exploring and enjoying the area's natural scenery.

Average Temperature Daytime: 50-60°F - Nighttime: 40-50°F

Weekly Weather Forecast for Islesboro

How to Book Your Islesboro Vacation Rental Home

What's our booking process?

Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Islesboro

More Top-Rated Vacation Rentals in Islesboro Area

Common Vacation Rentals Amenities

What amenities can you expect?

Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

  • Enjoy outdoor dining with a fully equipped patio or picnic area, perfect for savoring fresh seafood and local produce.
  • Relax on spacious decks that offer stunning views of the surrounding waters and lush landscapes.
  • Take advantage of private docks or waterfront access for boating, kayaking, or paddleboarding adventures.
  • Gather around an outdoor fire pit during cool evenings to share stories and enjoy the peaceful ambiance.
  • Make use of well-maintained gardens or landscaped yards to unwind amidst natural beauty.
  • Utilize outdoor grills or barbecues to prepare delicious meals while enjoying the fresh coastal air.
  • Participate in activities such as birdwatching or nature walks along scenic trails nearby the property.

Top Attractions Around Islesboro

What attractions are nearby?

During your stay, you'll find a variety of outdoor activities nearby, including scenic hiking trails and opportunities for boating, allowing you to fully enjoy the natural beauty of this coastal region.

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Family Activities

  • Explore the Islesboro Historical Society Museum: Discover local history and maritime heritage to enrich your family’s understanding of the region's past.
  • Enjoy a day at the local beach: Relax and build sandcastles on the pristine shores, perfect for seaside fun just minutes from your vacation rental.
  • Take a scenic nature walk: Traverse through wooded trails with your family, experiencing the natural beauty that makes this destination so special.
  • Participate in a boat tour: Embark on an aquatic adventure around the island, offering unforgettable views and wildlife sightings suitable for all ages.
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Adult Activities

  • Kayaking and Paddleboarding: Explore the scenic waters surrounding the area at your own pace by renting a kayak or paddleboard to enjoy a peaceful day on the ocean.
  • Wildlife Watching Tours: Embark on guided tours that will take you through the region’s rich natural habitats, offering opportunities to spot local seabirds and marine life.
  • Fishing Excursions: Take advantage of the region’s renowned fishing spots with a day trip designed for anglers seeking to catch Maine’s iconic fish species.
  • Nature Walks and Hiking: Discover serene trails along the coastline and through lush forests, perfect for immersing yourself in the natural beauty of this destination.

Islesboro Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Ahead for Local Experiences: Take the time to explore nearby local events and activities to truly immerse yourself in the region's unique charm.
  • Choose a Prime Location: Select a vacation rental situated close to the area's most sought-after spots to maximize your sightseeing and relaxation time.
  • Respect the Environment: Practice eco-friendly habits during your stay to help preserve the natural beauty that makes this destination special.
  • Communicate with Hosts: Engage with your rental hosts for personalized tips and insights, enhancing your experience of the area’s authentic offerings.

Transportation Options

  • Ferry Service: Regular ferries connect the mainland to this island destination, offering a scenic and convenient way to arrive at your vacation rental here.
  • Private Boat Charters: For a personalized experience, private boat charters provide flexible transportation around the region’s coastal waters and islands.
  • Car Rentals: Renting a car on the island allows you to explore the surroundings at your own pace, with options available nearby for ease of access.
  • Local Taxis and Ride-Sharing: Local taxi services and ride-sharing options offer quick, reliable transportation within this quiet region, perfect for getting to your vacation rental and around town.

Local Customs Options

  • Community Gatherings: Participating in local events and seasonal festivals is a cherished tradition that helps you connect with the area's close-knit community during your stay.
  • Seafood Traditions: Enjoying freshly caught lobster and other seafood delicacies is an integral part of the region’s culinary customs that you can experience firsthand here.
  • Maritime Heritage: Respect for maritime history and boat-related activities is evident, making it common to observe local boating customs and seaside celebrations.
  • Environmental Stewardship: The locals value sustainable practices and preserving natural beauty, encouraging visitors to follow eco-friendly guidelines while exploring here.

Frequently Asked Questions About Islesboro?

1. What are the top vacation rentals in Islesboro?

There are a lot of options in Islesboro. If you plan on staying in the Islesboro area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Islesboro:

2. Which vacation homes in Islesboro are best for families?

If you are looking for a family-friendly vacation home in Islesboro, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Islesboro:

3. How many Rentbyowner vacation rentals are available in Islesboro?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 203 in the Islesboro area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Islesboro. 

4. What is the cancellation policy for vacation rentals in Islesboro, Maine?

Cancellation policies vary by property, so it is important to review the specific listing details or contact the property owner directly to understand the terms and any applicable fees before booking.

5. Are there any additional fees associated with booking a vacation rental in Islesboro?

Additional fees such as cleaning fees, security deposits, or service charges are often outlined in the listing. Be sure to check the property details or reach out to the owner for complete fee information.

6. How do I confirm my reservation for a vacation rental in this region?

Reservations are typically confirmed through the booking platform once you finalize your selection and provide payment information. For further confirmation or special requests, contacting the property owner is recommended.

7. What amenities are usually included in vacation rentals around Islesboro, Maine?

Most properties offer amenities like Wi-Fi, fully equipped kitchens, and outdoor spaces, but it's best to review each listing for specific offerings to ensure they meet your needs.

8. Is it safe to stay in vacation rentals in the area during different seasons?

Safety standards for vacation rentals are maintained across the region, but always verify the property's safety features and read recent guest reviews to ensure a secure and comfortable stay.