Bailey Island vacation rentals

We found 170 vacation rentals — enter your dates for availability

Select from 27 homes, 25 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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Find out more about Bailey Island

Why visit Bailey Island

  • Stunning coastal scenery: Bailey Island features breathtaking ocean views and rugged cliffs, perfect for nature lovers.
  • Outdoor activities: Engage in sailing, fishing, and beach outings to fully experience Maine's beautiful waterfront.
  • Charming neighborhoods: Explore picturesque areas that blend relaxation with local culture and coastal charm.
  • Family-friendly atmosphere: Enjoy a welcoming environment that caters to families seeking both adventure and leisure.
  • Variety of accommodations: Choose from cozy cottages, oceanfront rentals, and inviting condos for your perfect getaway.

Popular types of accommodation in Bailey Island

Bailey Island offers a delightful selection of vacation rentals, perfect for your getaway. Whether you’re seeking a private vacation home, a charming cottage, or a cozy condo, you'll find accommodations that suit your needs. Enjoy the stunning views from oceanfront cottages or unwind at the inviting Sea Escape Cottages. With options like Little Harbor nearby, your ideal vacation awaits. Explore Bailey Island vacation rentals and discover the perfect spot for your next adventure.

  • Houses: The top choice among travelers, these homes offer spacious accommodations perfect for families or groups seeking comfort and privacy.
  • Cottages: These quaint and charming retreats provide a cozy atmosphere, ideal for couples or small families looking for a peaceful getaway.
  • Condos: A popular option, condos feature modern amenities and are often located near beaches, making them great for an enjoyable stay.
  • Apartments: Offering convenience and affordability, apartments are perfect for those wanting a home-like experience during their visit.
  • Cabins: Rustic and inviting, cabins provide a unique escape for nature enthusiasts seeking tranquility in a beautiful setting.**

Top attractions in and around Bailey Island

Bailey Island, Maine, is a perfect destination for outdoor enthusiasts and beach lovers. Explore stunning beaches, national parks, and picturesque island scenery. Visitors can enjoy activities such as sailing charters, fishing, and soaking in the beautiful Maine waterfront. Experience the local culture while taking in the breathtaking seaside views and charming fishing boats. Whether you're seeking relaxation or adventure, Bailey Island offers a delightful getaway.

  • Bailey Island Bridge: This historic bridge offers breathtaking views and a glimpse into the region's maritime culture. Its architectural charm and scenic surroundings make it a perfect spot for photography and leisurely strolls.
  • Casco Bay: Located a few miles from Bailey Island, Casco Bay is renowned for its stunning scenery and outdoor activities. Enjoy kayaking, sailing, or simply relaxing on the shores while soaking in the beautiful coastal atmosphere.
  • Popham Beach: About 11 miles away, Popham Beach features expansive sandy shores ideal for sunbathing and beachcombing. The gentle waves and picturesque views create a perfect setting for a day of relaxation by the ocean.

Things to do recommended for couples

For a romantic getaway in Bailey Island, consider a visit to the Portland Club, a luxurious private country club located 15 miles away. Enjoy intimate dining and stunning views, perfect for creating lasting memories with your loved one.

Things to do recommended for families

Families will love exploring the scenic tide pools at Land’s End, discovering local marine life. A visit to the charming Bailey Island Bridge offers stunning views, while the nearby beaches provide perfect spots for picnics and sandcastle building. Don’t miss the delicious lobster shacks for a true Maine experience.

Things to do recommended for groups

Groups visiting Bailey Island can enjoy a scenic lobster boat tour, explore the picturesque Coastal Maine Botanical Gardens, and savor fresh seafood at local eateries. Don't miss the chance to hike the stunning trails at nearby Land's End, offering breathtaking views of the Atlantic Ocean.

*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 Bailey Island

No matter if you're traveling with a group, spending time with family, bringing along your pets, or planning for an extended stay, it's important to prioritize your preferences. Here are some helpful Vrbo booking tips to consider.

  • Traveling to Bailey Island with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor areas for group get-togethers. Luckily, you can easily apply filters for all of these options, and more, on Vrbo.
  • Traveling to Bailey Island with young kids: Traveling with young kids can be quite a task. It's important to prioritize their comfort and safety, along with finding suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Bailey Island: For many families, a trip just isn't the same without their furry companions. If you relate to this, explore Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer essentials like feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Bailey Island: If you're in search of vacation rentals that offer special rates for stays of a month or more, you've come to the right place. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in and around Bailey Island

Bailey Island, Maine, offers a picturesque coastal vacation with breathtaking ocean views and rugged cliffs. Embrace the family-friendly atmosphere while exploring charming neighborhoods nearby that blend relaxation with cultural experiences. Enjoy outdoor activities and soak in the stunning scenery that defines this unique Maine destination. Whether it's a day at the beach or a leisurely stroll along the rocky shoreline, Bailey Island promises unforgettable memories for every traveler.

  • West Harpswell: West Harpswell is a charming neighborhood located 2 miles from Bailey Island, offering visitors a delightful mix of romantic ambiance, outdoor adventures, and cultural experiences. This picturesque area boasts a variety of recreational venues, including theaters and arts centers, making it perfect for those who appreciate the arts. Nature lovers can enjoy beautiful beaches and serene lakes, perfect for family outings or peaceful retreats. The local beaches are ideal for sunbathing, swimming, and picnicking, while the recreational areas provide opportunities for hiking and exploring the stunning coastal landscape.
  • Giant's Stairs: Situated around Bailey Island, Giant's Stairs is a breathtaking coastal area that beckons travelers with its outdoor, family-friendly, and beach-centric experiences. Accessible via footpaths, this scenic spot features dramatic rocky shorelines and stunning ocean views. Families will enjoy the nearby family beach, perfect for a day of fun in the sun, while the tourist precinct offers various shops and eateries to explore. The natural beauty of Giant's Stairs makes it an excellent location for leisurely walks, beachcombing, and creating lasting memories with loved ones.
  • Giant's Stairs Trail: Located near Bailey Island, the Giant's Stairs Trail is an enchanting route that offers visitors a rich cultural experience along with picturesque views. As you traverse the footpath, you'll encounter historical landmarks, including a historic bridge and monument, adding a sense of history to your journey. This trail is perfect for those who appreciate the blend of nature and culture, providing a serene escape as you explore the beautiful coastal landscape. Hikers and history buffs alike will find this trail a rewarding adventure, showcasing the unique charm of the area.

Best time to go to Bailey Island

If you're planning a trip to Bailey Island, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from June to August, while off-peak times, like January to March tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January26.4°F (-3.1°C)Light RainMostly SunnyLowSlightly Low
February27.1°F (-2.7°C)Light RainMostly CloudyLowSlightly Low
March33.6°F (0.9°C)Light RainMostly SunnyLowSlightly Low
April43.5°F (6.4°C)Light RainMostly SunnyAverageAverage
May53.2°F (11.8°C)Light RainMostly SunnyAverageAverage
June61.2°F (16.2°C)Light RainMostly SunnyHighSlightly High
July68.0°F (20.0°C)Light RainMostly SunnyHighSlightly High
August67.8°F (19.9°C)Light RainMostly SunnyHighSlightly High
September61.9°F (16.6°C)Light RainMostly SunnyAverageAverage
October52.2°F (11.2°C)Light RainMostly SunnyAverageAverage
November41.5°F (5.3°C)Light RainMostly SunnyAverageAverage
December33.1°F (0.6°C)Light RainMostly SunnyAverageAverage

Booking with Vrbo is simple

Are you seeking ways to save on your upcoming trip? Being flexible with your travel dates can lead to better deals, as prices often fluctuate. Additionally, consider booking a longer stay to unlock even greater savings. To discover a Vrbo property that aligns with your budget, utilize our filters to sort by price, location, and the type of vacation rental you prefer. We're here to help you find the perfect option.

Unlock savings with One Key

Reserve a qualifying Vrbo for your group getaway and receive OneKeyCash on your complete booking. Being the planner truly has its rewards. When you enroll in our travel rewards program, One Key, you'll gain access to exclusive member discounts and earn OneKeyCash on eligible bookings. Sign up today and begin enjoying your savings.

Vrbo Trips: Planning made easy

Vrbo's cutting-edge Trip Board offers you a dedicated space to plan new trips, pick up right where you left off, and manage your travel arrangements with ease. You can easily find properties you've saved or booked in the sections for Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Soak up Bailey Island's alluring old-world vibe

Jutting off Maine's ruggedly beautiful coast into the deep blue Atlantic, Bailey Island lures visitors from far and wide thanks to its pristine shorelines, its sedate way of life and its beguiling old-world ambience. Bailey is located in the town of Harpswell, home to one of Maine's last remaining working harbors, which you'll invariably find packed with gently bobbing fishing boats and yachts. The island is also scattered with quirky boutiques and welcoming inns serving hearty home-cooked fare. Bailey Island vacation rentals range from cozy cottages perfect for a romantic getaway to sprawling family homes where you could host a big family get-together.

Bailey Island's natural wonders

As you approach the island, it's certainly worth stopping to marvel at the distinctive Bailey Island Bridge. Constructed in the 1920s, it was recognized in 1984 as a Historic Civil Engineering Landmark, as it was believed to be the only bridge on the planet made of granite cribstone. Once you've settled into your Bailey Island vacation rental, be sure to make a pit-stop at Mackerel Cove, a picture-postcard harbor where the shimmering water is ideal for swimming in the summer, and crabbing when it's cooler outside. For further spectacular coastal scenery, take a short hike to the Giant's Stairs, a dramatic rocky outcrop that dates back over 500 million years, where crashing waves can often be seen in the gleaming sunshine.

Shopping and seafood feasts on Bailey Island

Discerning shoppers will be enthralled by Bailey Island's array of independent stores, where you can pick up everything from one-of-a-kind artworks to exquisite hand-crafted jewelry to chic designer fashion. Bailey's dining scene is similarly captivating, Freshly-caught seafood naturally features prominently on many menus, so you can look forward to feasting on creamy clam chowder, buttery lobster rolls, decadent deep-fried clams or locally harvested oysters. If you fancy learning how your dinner was caught, join a lobster harvesting tour, where a local expert will talk you through the history of lobster trapping as you head out to sea, before showing you precisely how it's done.

Vivid seasons on Bailey Island

Bailey Island vacation rentals draw in big numbers of visitors during the sun-dappled months of summer. The days are long, warm and sunny, ideal for afternoons at sea or strolling down coastal paths. Winters, by contrast, are rather cold, with temperatures frequently tumbling below freezing and a fair amount of snowfall. Spring and fall are great times to visit, with mild to warm temperatures and fewer out-of-towners competing for prime accommodation.

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)
  • Popham Beach State Park (9.8 mi / 15.7 km)
  • Popham Beach (10.7 mi / 17.3 km)
  • Desert of Maine (11.7 mi / 18.8 km)
  • Thomas Point Beach (12.1 mi / 19.4 km)
  • East End Beach (13.2 mi / 21.2 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 best area to stay in Bailey Island, Maine, United States of America when booking a vacation rental?
When considering the best area to stay in Bailey Island, Maine, you might want to explore the charming neighborhood near the shoreline. This area is known for its idyllic views of the ocean and offers a variety of vacation rental options, from cozy cottages to scenic beachfront homes. With several properties available, visitors can find accommodations that suit their preferences and group sizes.

One of the top attractions in this area is the famous Bailey Island Bridge, which provides stunning views and is a great spot for photography. Additionally, the local beaches, such as the beautiful Lands End Beach, offer opportunities for swimming, sunbathing, and exploring tide pools. The area is also home to unique shops and delightful seafood restaurants, where you can savor the fresh catch of the day.
How much does it cost to rent a vacation home in Bailey Island?
Prices for vacation rentals in Bailey Island 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 Bailey Island 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 Bailey Island vacation house rentals?
You can find great discounts on house rentals in Bailey Island 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 Bailey Island?
For renting a beach house in Bailey Island, travelers should focus on areas along the coastline that provide stunning ocean views and easy access to the beach. The area around the Bailey Island Bridge offers picturesque spots with properties that often come equipped with amenities such as spacious decks, outdoor grills, and private pathways leading directly to the shore. Many of these rentals are ideal for families, featuring multiple bedrooms and open living spaces superb for gathering after a day of beach activities.

Additionally, the vicinity of Land's End is a fantastic choice, where visitors can find charming cottages and larger homes that boast amenities like fire pits, fully stocked kitchens, and sometimes private docks for those interested in kayaking or boating. This area is also conveniently located near local eateries and shops, allowing guests to experience the local culture and cuisine.

Furthermore, the nearby Giant's Stairs at the southern tip of the island offers breathtaking views and unique geological formations, making for a great day trip. Properties in this region often emphasize outdoor living, with options for hammocks, picnic areas, and easy access to scenic walking trails that provide a closer connection to nature.
What is the most popular type of vacation rental accomodation in Bailey Island?
In Bailey Island, vacation houses and cottages are the most popular types of rentals, with around 24 of each available throughout the area. These properties are often situated close to the coast, providing stunning views of the ocean and easy access to local beaches. Most vacation houses and cottages come equipped with fully stocked kitchens, cozy living spaces, and outdoor decks or porches for enjoying the fresh sea breeze.

Additionally, there are several apartments, cabins, and condos available, offering varied accommodations for different group sizes and preferences. Cabins typically feature rustic charm and are surrounded by natural beauty, while condos may provide more modern amenities and communal facilities.
Are there any family house rentals in Bailey Island?
In Bailey Island, Maine, there are numerous family-friendly vacation rentals available, totaling around 49 options. This charming locale is superb for families looking to enjoy the beauty of coastal living. Many of the properties feature spacious living areas, fully equipped kitchens, and outdoor decks or patios where families can relax and take in the ocean views.

Visitors can also find homes with amenities such as game rooms for entertainment and private yards for kids to play in. Close to the rentals, families can explore nearby attractions like the scenic Bailey Island Bridge, which provides stunning views and great photo opportunities, or enjoy a day at the beach. The area's vibrant community offers fresh seafood restaurants and local shops, adding to the overall experience.
Can I find long-stay vacation rentals in Bailey Island?
A long-stay vacation rental in Bailey Island 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 Bailey Island?
In Bailey Island, visitors will find a variety of pet-friendly house rentals that cater to those traveling with furry companions. With 22 options available, these rentals often feature amenities such as spacious backyards, outdoor decks, and fully equipped kitchens, allowing for a comfortable stay while enjoying the coastal atmosphere. Many properties are designed for families or groups, offering multiple bedrooms and living spaces to relax after a day of exploring the island.

The area is well-known for its scenic beauty, with nearby points of interest like the Harpswell Heritage Land Trust trails, where pets are welcome on leashes, providing opportunities for hiking and enjoying nature together. Additionally, local parks and waterfront areas offer further options for outdoor activities with pets, making Bailey Island an ideal destination for travelers looking to enjoy both the ocean and the company of their furry friends.
Are there any remote work vacation rentals in Bailey Island?
In Bailey Island, Maine, there are numerous options for remote work vacation rentals, with around 55 available. This charming coastal destination offers a unique blend of natural beauty and tranquility, making it an ideal spot for those looking to work remotely while enjoying the serene surroundings. Many properties come equipped with reliable Wi-Fi, allowing for seamless connectivity, and often feature comfortable workspaces within the accommodations.

Travelers can expect amenities such as cozy living areas, fully equipped kitchens for convenient meal preparation, and outdoor spaces where one can unwind after a day of work. The island's picturesque landscapes, including stunning ocean views and nearby beaches, provide a superb backdrop for breaks or leisurely activities. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Bailey Island vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Bailey Island 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 Bailey Island?
In Bailey Island, popular vacation rental amenities include fully equipped kitchens, allowing guests to prepare their own meals with ease. Many properties also feature decks or patios, providing an excellent space for outdoor relaxation while enjoying the coastal views. Onsite parking is commonly available, making it convenient for travelers with vehicles. Additionally, rentals often include coffee and tea makers, great for those who enjoy morning brews. For those looking to stay active, fitness facilities are typically located nearby, offering options for exercise during their stay.
How early should I book a Bailey Island vacation rental?
Book your Bailey Island 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 Bailey Island, Maine, United States of America?
In Bailey Island, Maine, visitors can enjoy a variety of attractions that showcase the area's natural beauty and maritime charm. The island is renowned for its scenic coastal views, particularly from Land's End, where the rocky shoreline meets the Atlantic Ocean, offering stunning photo opportunities and a peaceful atmosphere. Vacation rentals nearby often provide easy access to this picturesque spot.

Another highlight is the iconic Bailey Island Bridge, which connects the island to the mainland and offers a lovely view of the surrounding waters. The area is also famous for its unique granite formations and tide pools, superb for exploration and discovering local marine life.

For those interested in a maritime experience, the nearby Giant's Stairs provides a dramatic coastal landscape with smooth granite ledges and a great spot for tide pooling and enjoying the ocean breeze. Additionally, visitors can explore the local art scene at the Bailey Island Art Gallery, showcasing works inspired by the area's breathtaking scenery.

Dining options abound, with several seafood restaurants offering fresh catches and stunning views.
Can I change or cancel my Bailey Island home rental booking on Vrbo?
To find Bailey Island 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 Bailey Island 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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