Bailey Island vacation rentals

We found 153 vacation rentals — enter your dates for availability

your current months are March, 2024 and April, 2024.
March 2024
April 2024
Select from 28 homes, 32 cottages, and other vacation rentals in Bailey Island to find one that's perfect for your trip. Vacation homes offer the best amenities for your family, friends, or furry companion, such as parking and a washer and dryer. At the end of the day, you'll be sure to find a rental that has what everyone needs, including a place that's non-smoking or offers accessibility.

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Take in the waterfront beauty of Bailey Island

Enjoy the monuments and other features of Bailey Island. Renowned for its island views, shopping and fishing, this city welcomes all visitors. Are you looking for specific amenities for your getaway? Many of our vacation rentals feature full kitchens and laundry facilities.

Activities and attractions in Bailey Island

Do you want to find things to do during your stay? Venture out of your cozy vacation rental and check out everything that makes Bailey Island a fun spot to vacation. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Casco Bay Lines Ferry Terminal (13.9 mi / 22.4 km)
  • Land's End Gift Shop (1.3 mi / 2.1 km)
  • Ash Cove Pottery (1.4 mi / 2.3 km)
  • Paddleworks (1.7 mi / 2.8 km)
  • Wilbur's of Maine Chocolate Confections (9.7 mi / 15.6 km)
  • Capt Lyman Stuart, LLC (10.9 mi / 17.6 km)

Exploring the natural landscape of Bailey Island

Whether you're an active traveler or just want to take in the scenery, you'll be sure to find the perfect setting for your vacation in Bailey Island. Here are a few of the area's most enchanting features, all within 30 miles (48.2 km) of the city center:

  • Casco Bay (2.8 mi / 4.6 km)
  • Wolfe's Neck Woods State Park (7.5 mi / 12.1 km)
  • Popham Beach State Park (9.8 mi / 15.7 km)
  • Popham Beach (10.6 mi / 17.1 km)
  • Desert of Maine (11.7 mi / 18.8 km)
  • Sand Beach (12 mi / 19.3 km)

Transportation to and around Bailey Island

The nearest airport is in Portland Intl. Jetport Airport (PWM), located 17 mi (27.3 km) from the city center. If you're unable to find a flight that fits your schedule, you could book a flight to Wiscasset, ME (ISS), which is 21.1 mi (33.9 km) away.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Bailey Island?

The most desirable types of vacation rentals in Bailey Island are cottages. Ready for more choices? Vrbo has numerous options to match our guests' unique needs, so you'll see properties in lots of sizes and shapes. The perfect fit is waiting for you — discover yours today.

How much does it cost to rent a vacation rental in Bailey Island?

Length of stay, property type and time of year are some of the conditions that can affect the price of a vacation home. Simply enter your travel dates to find your dream escape. From homey country cottages to expansive villas, all Vrbo vacation rentals offer amazing value.

How much does it cost to rent a beach house in Bailey Island?

The average price for a vacation home close to the beach in Bailey Island depends on when you're visiting the area and the size and type of property you're looking for. You can find prices quickly and easily on Vrbo by entering your destination and preferred travel dates. Then use our filters to pick the number of bedrooms and amenities that you need, like air conditioning, WiFi and a pool.

What are popular rental amenities in Bailey Island?

A fireplace, a chef and a barbecue grill are the most popular rental amenities in Bailey Island. Whether you plan to go on your own, with your significant other or a group of friends, Vrbo will help you find a vacation rental that matches your tastes with all the options you need.

What are the top attractions for families in Bailey Island?

Keeping the kids amused during your Bailey Island vacation is a snap with these family-friendly attractions:

  • Wolfes Neck Farm
  • Paddleworks
  • Wolfes Neck Woods State Park

Can I find two-bedroom vacation rentals in Bailey Island?

Bailey Island has 15 two-bedroom properties for you to select from. Discover a vacation home with all the space and comfort you're looking for at a price that won't break the bank on Vrbo.

Are there vacation rentals with WiFi in Bailey Island?

Bailey Island has 16 vacation rentals with WiFi, so you'll be able to stay connected when you're away. Simply check the "WiFi" box in our search filter for a list of properties with this feature. From streaming movies with your family to scrolling social media, these Vrbo homes make it easy to go online.

How old do you have to be to rent a vacation rental in Bailey Island?

The minimum age is usually 16, 18 or 21. It can change across properties on Vrbo, so look at the rules of your chosen Bailey Island vacation rental before booking your stay.

How long can I rent a vacation rental in Bailey Island for?

It's really down to the Bailey Island property. To view a list of options offering extended stays, just enter your travel dates and number of people into Vrbo. You can look forward to having the entire place to yourself, along with comforts such as air conditioning, a kitchen and a backyard where the kids can play. Keep an eye out for any long-term stays that offer discounted weekly or monthly prices.

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