Bailey Island vacation rentals

We found 162 vacation rentals — enter your dates for availability

Select from 26 homes, 27 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.
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more
  • More for less

    More space, more privacy, more amenities — more value
  • A place for everyone

    We stand for diversity, inclusion and families everywhere.
    Learn more

Find out more about Bailey Island

Find out more about Bailey Island

Why visit Bailey Island

  • Scenic Coastal Views: Enjoy breathtaking views of the coastline and picturesque beaches, perfect for relaxation and photography.
  • Outdoor Adventures: Engage in a variety of outdoor activities, including hiking, kayaking, and sailing, amidst stunning natural landscapes.
  • Charming Accommodations: Choose from cozy waterfront cottages and spacious vacation homes, ideal for a memorable stay.
  • Local Culture: Immerse yourself in the vibrant culture of nearby neighborhoods, offering unique shops and dining experiences.
  • Family-Friendly Atmosphere: Experience a welcoming environment that's perfect for families, ensuring fun for all ages.

Popular types of accommodation in Bailey Island

Planning your getaway to Bailey Island? The first step is finding the perfect place to stay. Discover a variety of vacation rentals, from cozy waterfront cottages to spacious houses and inviting condos. Whether you’re looking for a charming seaside retreat or a comfortable home base for your adventures, Bailey Island has the ideal accommodations to make your stay unforgettable. Explore our selection of Bailey Island vacation rentals today.

  • Houses: The top choice for visitors to Bailey Island, offering spacious and comfortable accommodations ideal for families and groups.
  • Cottages: A popular option for a quaint and cozy experience, perfect for those seeking a charming seaside getaway.
  • Condos: A great alternative providing modern amenities and often stunning views, suitable for couples or small families.
  • Apartments: A versatile choice for travelers seeking convenience and a home-like atmosphere during their stay.
  • Cabins: Rustic retreats nestled in nature, perfect for those wanting to immerse themselves in the beautiful surroundings of Maine.**

Top attractions in and around Bailey Island

Bailey Island, Maine, offers a perfect setting for outdoor and beach vacations, featuring stunning scenery and a variety of attractions. Visitors can explore the local beaches, enjoy boat charters, and take in the natural beauty of state parks and the island itself. Whether you're seeking cultural experiences or simply a relaxing seaside getaway, Bailey Island provides an array of activities to make your vacation unforgettable.

  • Casco Bay: A picturesque bay offering beautiful beaches and stunning outdoor scenery, perfect for kayaking, sailing, or simply relaxing by the water.
  • Bailey Island Bridge: A historic bridge that connects Bailey Island to the mainland, showcasing rich local culture and providing breathtaking views of the surrounding landscape.
  • Bowdoin College: A prestigious historic college located 12 miles away, known for its stunning architecture and vibrant campus culture, making it a great spot for a leisurely stroll.

Things to do recommended for couples

For a romantic getaway on Bailey Island, consider paddleboarding at Paddleworks for adventure, unwinding at the luxurious Portland Club, or enjoying live music at Port City Music Hall. Each experience promises to create unforgettable memories together in this charming coastal town.

Things to do recommended for families

Families visiting Bailey Island can enjoy a thrilling day at Hadlock Field, just 15 miles away, and experience the relaxation of Fort Williams Park, located 13 miles away. Don’t miss the entertaining Portland Observatory, only 14 miles from the island, perfect for creating lasting memories together.

Things to do recommended for groups

Groups visiting Bailey Island can shop at the LL Bean Flagship Store or explore the Maine Mall for entertainment and dining. For adventure, the Desert of Maine offers a unique outdoor experience, making it a perfect spot for family fun and group activities.

*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

If you're traveling with a group, your family, bringing pets, or seeking extended stays, be sure to prioritize your filters accordingly. Here are some helpful Vrbo booking tips for you.

  • Traveling to Bailey Island with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor area for group gatherings. Luckily, you can easily filter for these options and much more on Vrbo.
  • Traveling to Bailey Island with young kids: Traveling with young kids can be quite demanding. It's important to prioritize their comfort and safety, along with providing suitable amenities like a private pool. Additionally, thinking about how close you are to family-friendly attractions is a wise choice.
  • Taking your pets with you to Bailey Island: For many families, a vacation wouldn't be the same without their beloved pets. If this resonates with you, explore Vrbo listings that welcome furry companions. Many of these pet-friendly properties offer essentials like food 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 offering discounts for stays of a month or longer, you've come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on monthly rental options. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria.

Where to stay near Bailey Island

Bailey Island, Maine, is a charming getaway perfect for a beach vacation. With stunning coastal views and a family-friendly atmosphere, it offers an ideal setting for outdoor adventures and relaxation. Nearby cities and neighborhoods enhance your experience with vibrant culture and recreational activities. Whether you're seeking a cozy vacation home or simply want to soak up the scenic beauty, Bailey Island promises a memorable escape for all travelers.

  • West Harpswell: Nestled only 2 miles from Bailey Island, West Harpswell is a charming neighborhood known for its stunning outdoor scenery and romantic atmosphere. Visitors can indulge in various outdoor activities at its recreational areas or enjoy live performances at local theaters. Nature lovers will appreciate the nearby lake and beach, as well as the breathtaking landscapes of the national state park, making it a perfect spot for a day of exploration or a serene picnic by the water.
  • Orrs Island: Located 3 miles away from Bailey Island, Orrs Island offers a picturesque escape with its beautiful beaches and vibrant outdoor activities. This island city is a haven for water sports enthusiasts and families looking for a fun-filled day at the beach. Enjoy recreational areas that provide educational programs and outdoor experiences for all ages. The local beaches and lakes are perfect for sunbathing, swimming, or simply relaxing while soaking in the natural beauty that surrounds you.
  • Great Island: Just 4 miles from Bailey Island, Great Island is a tranquil getaway that emphasizes outdoor and beach experiences, making it ideal for couples seeking a romantic retreat. The island is surrounded by pristine beaches and serene lakes, providing ample opportunities for swimming, sunbathing, and peaceful walks along the shoreline. Whether you're looking to unwind or embark on an adventure, Great Island's natural charm is sure to captivate your heart.

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 a breeze

Looking to save on your next vacation? Consider being flexible with your travel dates, as prices can fluctuate. Additionally, opting for a longer stay often results in significant savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to search by price, location, and rental type. We're here to help you find the perfect getaway.

Save more with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on your booking. Being the planner has its perks. When you join our travel rewards program, One Key, you can easily access exclusive member discounts and earn OneKeyCash on eligible reservations. Sign up today and start enjoying the savings.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board provides a convenient platform for you to plan new trips, keep track of your existing plans, and manage your bookings efficiently. Your saved or reserved properties are neatly categorized into Potential, Upcoming, or Current Trips for easy access. To discover more about 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 when booking a vacation rental?
When planning a vacation rental in Bailey Island, Maine, the best area to consider is the charming neighborhood of Mackerel Cove. This picturesque spot offers stunning views of the ocean and is conveniently located near some of the island's top attractions. One of the highlights is the iconic Bailey Island Bridge, which provides a scenic connection to the mainland and is a favorite for photographers and nature lovers alike. Mackerel Cove is also close to the famous Land's End Gift Shop, where visitors can find unique souvenirs and enjoy delicious local cuisine.

Another excellent option is the area around Cook's Lobster House, which not only offers delightful dining experiences but also serves as a great starting point for exploring the surrounding coastline. This region boasts a variety of vacation rentals, providing numerous options for travelers seeking both cozy cottages and larger homes with ocean views.
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, Maine, the area around the island's southern tip offers stunning ocean views and easy access to the rocky coastline. Look for properties near Land's End, where you can find charming vacation homes that often feature large decks for enjoying sunsets, outdoor grilling areas, and direct paths to the beach. Many of these rentals are equipped with modern kitchens, cozy living spaces, and sometimes even fire pits for evening gatherings.

Additionally, the vicinity of the Bailey Island Bridge provides a picturesque setting, with nearby properties showcasing classic New England architecture. These homes typically offer ample space for families or groups, often featuring amenities such as laundry facilities and multiple bedrooms with ocean views. The nearby waterfront also has opportunities for kayaking and fishing, making it a great spot for outdoor enthusiasts.

For those interested in local culture, the area is close to several quaint shops and restaurants that serve fresh seafood and local fare. The scenic walking trails along the shore, particularly near the Giant's Stairs, provide opportunities for exploration and relaxation, making this region an ideal choice for beach house rentals.
What is the most popular type of vacation rental accomodation in Bailey Island?
In Bailey Island, cottages are the most popular type of vacation rental, with around 30 available throughout the area. These charming properties often feature rustic decor, fully equipped kitchens, and cozy living spaces, making them ideal for a relaxing getaway. Many cottages also provide outdoor decks or porches where guests can enjoy the stunning coastal views and fresh sea air.

In addition, there are about 25 vacation houses, which offer larger accommodations suitable for families or groups. These homes typically include multiple bedrooms, spacious living areas, and often direct access to the beach or waterfront.
Are there any family house rentals in Bailey Island?
In Bailey Island, Maine, there are numerous family-friendly house rentals available, with around 53 options to choose from. This picturesque locale is known for its stunning coastal views and charming atmosphere, making it an excellent destination for families. Many of the properties feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces great for enjoying the fresh ocean air.

Visitors can also find amenities like Wi-Fi, laundry facilities, and sometimes even private decks or patios where families can gather and relax. The island's proximity to beautiful beaches and scenic walking trails enhances the experience, allowing guests to easily explore the natural beauty of the area.

Additionally, being close to attractions such as the iconic Bailey Island Bridge and local seafood dining options adds to the charm. See all family-friendly rentals in Bailey Island.
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, Maine, there are several pet-friendly house rentals available, making it a great destination for travelers looking to enjoy a coastal getaway with their furry companions. Many of these vacation rentals come with amenities such as fully equipped kitchens, outdoor decks with ocean views, and access to private beaches or shared waterfront areas.

The island is known for its picturesque scenery, with rocky shorelines and charming lighthouses that can be enjoyed during leisurely walks with pets. Additionally, nearby parks and nature trails provide ample opportunities for outdoor adventures, allowing visitors to explore the natural beauty of the area while keeping their pets active. See all pet-friendly rentals in Bailey Island.
Are there any remote work vacation rentals in Bailey Island?
In Bailey Island, Maine, travelers can find a variety of remote work-friendly vacation rentals, with around 59 options available. The island is known for its stunning coastal scenery and charming atmosphere, making it an ideal setting for those looking to balance work and relaxation. Many of these properties come equipped with essential amenities for remote work, including desks, Wi-Fi, and comfortable office setups featuring desk chairs and computer monitors.

Staying in this picturesque area allows guests to enjoy the beauty of the coastline while having the convenience of a functional workspace. The proximity to local attractions such as the famous Bailey Island Bridge and nearby parks offers opportunities for outdoor activities during breaks. 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 well-equipped kitchens, allowing travelers to prepare their own meals with ease. WiFi is commonly available, making it convenient for guests to stay connected. Many rentals also feature patios or decks, providing outdoor spaces to relax and enjoy the coastal views. Additionally, a coffee or tea maker is often included, ensuring guests can start their day with a warm beverage while taking in the serene island atmosphere.
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?
In Bailey Island, visitors can enjoy a variety of attractions that highlight the island's natural beauty and coastal charm. The iconic Giant's Stairs, a series of granite rock formations along the shoreline, offers breathtaking views of the ocean and is a popular spot for photography and exploration. Nearby, the Bailey Island Bridge provides picturesque vistas and connects the island to the mainland, making it a noteworthy place to visit.

The area around Land's End, known for its stunning views and serene atmosphere, is superb for leisurely walks and enjoying the coastal landscape. The local beaches, such as Cedar Beach, provide opportunities for swimming, sunbathing, and beachcombing. Additionally, the island features quaint shops and eateries where visitors can sample fresh seafood and local delicacies, further enriching their experience.
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 flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
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.