Discover Your Perfect Bailey Island Vacation Homes

Bailey Island Luxury Rentals

10.0 (1 Review)
House
Oceans Edge Private Home
  • Air Conditioner
  • Parking
  • Pet Friendly
View Availability
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Bailey Island Pet Friendly Vacation Rentals

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Bailey Island Large Vacation Homes

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Why Choose Rent By Owner for your Bailey Island 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 Bailey Island

When should you plan your Vacation Rentals stay?

Knowing the best time to visit is essential for enjoying your stay here, as seasonal variations can influence weather, activities, and overall experience in this charming coastal area of Maine.

Peak Season Highlights

spring
June to August

During the summer months, this destination experiences warm weather and long daylight hours, making it perfect for outdoor activities and exploring the scenic coastal surroundings.

Average Temperature Daytime: 75-80°F - Nighttime: 60-65°F
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September to October

Early fall brings mild temperatures and vibrant foliage, creating a picturesque setting that appeals to visitors seeking the region's natural beauty and tranquility.

Average Temperature Daytime: 65-70°F - Nighttime: 50-55°F

Off-Season Highlights

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November to February

The winter months are quieter with cooler temperatures, offering a peaceful retreat for those who enjoy seasonal landscapes and a more relaxed atmosphere.

Average Temperature Daytime: 40-45°F - Nighttime: 25-30°F
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March to May

Spring sees a gradual warming trend and blossoming scenery, attracting visitors looking for fewer crowds and the serene beauty of the area's emerging greenery.

Average Temperature Daytime: 50-60°F - Nighttime: 35-40°F

Weekly Weather Forecast for Bailey Island

How to Book Your Bailey Island 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 Bailey Island

More Top-Rated Vacation Rentals in Bailey Island 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 direct access to scenic waterfronts with private or shared beach areas.
  • Take advantage of outdoor grilling stations perfect for seaside cookouts.
  • Relax on spacious decks or patios that offer stunning views of the coastal scenery.
  • Make the most of outdoor dining spaces ideal for alfresco meals by the water.
  • Utilize well-maintained lawns and gardens to unwind in nature’s serenity.
  • Explore nearby walking trails or pathways to immerse yourself in the region's natural beauty.
  • Benefit from boat docks or slips, making it easy to enjoy boating or fishing adventures here.

Top Attractions Around Bailey Island

What attractions are nearby?

Here, you can enjoy a variety of outdoor activities such as scenic walks along rugged coastlines, exploring picturesque lighthouses, and engaging in water-based pursuits like kayaking and fishing, all within easy reach of your vacation rental in Bailey Island, Maine.

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Family Activities

  • Cribstone Granite Bridge: Walk along this unique bridge and enjoy stunning views of the rocky shoreline, perfect for family photos and exploring nature.
  • Island Inn Nature Trails: Discover scenic trails around the inn that offer a great opportunity for family hikes and wildlife spotting in this picturesque region.
  • Rockport Marine Park: Spend a relaxing day at this nearby park where kids can play and the whole family can enjoy waterfront activities with beautiful ocean vistas.
  • Bass Harbor Lighthouse Cruises: Embark on a boat tour to see historic lighthouses and learn about the area’s maritime history, ideal for family adventures here.
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Adult Activities

  • Boating and Sailing: You can explore the scenic coastlines and hidden coves by renting a boat or joining a sailing tour around this picturesque region.
  • Seafood Dining Experiences: Indulge in fresh, locally caught seafood at renowned waterfront restaurants that showcase the region’s culinary delights.
  • Walking and Biking Trails: Discover the area's natural beauty on scenic trails perfect for walking or biking, offering stunning views of the coastline and lush landscapes.
  • Historical Site Visits: Immerse yourself in the local heritage by exploring historic sites and landmarks that tell the story of this charming destination.

Other Places to Stay in Bailey Island, ME

Bailey Island Bridge
Bailey Island Bridge Vacation Rentals
Cobwork Bridge
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Land's End Gift Shop
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Ragged Island
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More Places to Stay Near Bailey Island

Bailey Island Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Your Activities Early: Book outdoor excursions and boat trips in advance to make the most of the region’s scenic coastal beauty.
  • Explore Local Cuisine:** Sample fresh seafood and regional specialties at local eateries to immerse yourself in the area's culinary culture.
  • Visit Nearby Nature Spots:** Take advantage of nearby parks and beaches for relaxing days surrounded by the natural charm of this destination.
  • Choose the Right Accommodation:** Select a centrally located vacation rental to enjoy easy access to all the highlights and hidden gems here.

Transportation Options

  • Car Rentals: Renting a car provides you with the flexibility to explore all that the region around Bailey Island offers at your own pace.
  • Public Transit: Local bus services connect you to key destinations on and around this picturesque part of Maine, making it a convenient transportation option.
  • Taxi and Rideshare Services: Taxis and rideshare apps are readily available for quick, door-to-door transportation during your stay in this charming area.
  • Bicycle Rentals: Biking is a popular way to enjoy the scenic views here, with rental shops offering bikes suitable for all ages and skill levels.

Local Customs Options

  • Clam Shucking Tradition: Locals often participate in traditional clam shucking, a cherished activity that connects visitors to the region's maritime heritage.
  • Fishing Etiquette: Respectful fishing practices are a cornerstone here, emphasizing sustainable methods and quiet reverence for the area's abundant marine life.
  • Seafood Celebrations: The community takes pride in hosting seafood festivals that highlight locally caught shellfish and Maine’s renowned culinary culture.
  • Historic Maritime Customs: Maritime customs, including lighthouse visits and boat parades, reflect the area's long-standing relationship with the Atlantic Ocean.

Frequently Asked Questions About Bailey Island?

1. What are the top vacation rentals in Bailey Island?

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

2. Which vacation homes in Bailey Island are best for families?

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

3. How many Rentbyowner vacation rentals are available in Bailey Island?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 184 in the Bailey Island 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 Bailey Island. 

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

Cancellation policies vary depending on the individual listing. It’s important to review the specific rental's terms before booking or contact the owner directly to clarify their policy.

5. Are there any restrictions or house rules I should be aware of when booking a vacation rental here?

Each property may have its own rules regarding check-in times, pet policies, smoking, and other restrictions. Be sure to read the property description carefully or reach out to the host for detailed information.

6. How do I confirm the availability of a vacation rental in this region?

Availability can be checked directly through the listing calendar by the owner or manager. For questions about dates or to make a reservation, contacting the host is recommended.

7. What amenities are typically included in vacation rentals in Bailey Island, Maine?

Most listings include amenities such as Wi-Fi, fully equipped kitchens, parking, and outdoor spaces. Specific details are provided in each property's description, so review those carefully or ask the owner for more information.

8. Is it safe to stay in a vacation rental in this area during the off-season?

Many properties remain available year-round, with safety and comfort considerations detailed in the listing. For peace of mind, communicate directly with the owner about safety measures and seasonal conditions.