Bailey Island holiday rentals

We found 152 holiday 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 holiday rentals in Bailey Island to find one that's perfect for your trip. Holiday homes offer the amenities that you expect for your stay with friends, family or just your pet, such as air conditioning and a pool. Whatever you're looking for, you're sure to find a property to rent to meet everyone's needs, including a place that is accessible or non-smoking.

Find spaces that suit your style

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  • More quality time
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  • All the privacy of home
    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less
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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 holiday rentals feature full kitchens and laundry facilities.

Activities and attractions in Bailey Island

Are you hoping to discover top things to see and do during your stay? Venture out of your holiday home and check out everything that makes Bailey Island a one-of-a-kind holiday spot. Here are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • 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 looking for fun outdoor activities or just want to spend some time taking in the scenery, Bailey Island is a great place to get outside. These are a few of the area's most stunning features, all within 30 miles (48.2 km) of the city centre:

  • 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)

Transport to and around Bailey Island

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

Frequently asked questions

What is the most popular type of holiday home accommodation in Bailey Island?

The most desirable types of holiday homes 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 holiday home in Bailey Island?

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

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

The average price for a holiday 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 home amenities in Bailey Island?

A fireplace, a chef and a barbecue grill are the most popular home 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 holiday home 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 holiday is a snap with these family-friendly attractions:

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

Can I find two-bedroom holiday homes in Bailey Island?

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

Are there holiday homes with WiFi in Bailey Island?

Bailey Island has 16 holiday homes 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 holiday home 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 holiday home before booking your stay.

How long can I rent a holiday home 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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