Discover a selection of 148 vacation rentals in Bailey Island that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including WiFi and air conditioning. Prices start at $380 per night, and houses and cottages are popular options for a stay in Bailey Island. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Bailey Island
Destination guide

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.

Things to do

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.

Natural features

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)
  • East End Beach (13.2 mi / 21.2 km)
  • Willard Beach (13.3 mi / 21.4 km)
How to get there

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.

What are the top vacation rentals in or near Bailey Island?

Deluxe villas, tranquil houseboats and quaint cottages — everyone's ideal escape is different. Whatever your tastes, you're sure to find something to tantalize you among these top vacation rentals in Bailey Island:

  • "1890 Summer Cottage On An Ocean Bluff": This Great Island property offers 5 bedrooms and is highly rated among visitors. Conveniences such as a blender and a garden are on hand to make your stay a comfy one.
  • "The Nugget - Perfect 1 Bedroom Cottage. Across From Mackerel Cove": Put your bags down and your feet up at this top pick in New England. It features 1 bedroom, heating, a fridge and more.

For even more great options, use the search bar at the top of the page to find the perfect Bailey Island vacation rental for you.

Can I find log cabins to rent in or near Bailey Island?

Whether you want to spend your getaway chasing outdoor adventure or reconnecting with your friends, we've got lovely log cabins where you can do both. Take a peek at these favorites in and around Bailey Island:

  • "Cozy Log Cabin - Walking Distance To Morse Mountain And 3 Miles From Popham Beach": This terrific vacation home is an ideal base if you love playing in nature. Surfing and boogie boarding and kayaking are several activities you can do in the area when you're not chilling in your cozy cabin.
  • "Year Round Log Cabin Built In 1989 On Long Lake - 2": Stay in and enjoy the quiet atmosphere or experience some of the exciting activities nearby, such as water skiing and kayaking. Idle or active, the choice is yours.

What are the top-rated vacation rentals for weekend getaways in or near Bailey Island?

Escape the daily grind at one of our weekend getaways in or near Bailey Island. Whether you'd like to hang out with friends or spend precious time with the family, there'll be something to suit your needs. Here are a few places we think you'll love:

  • "Maine Oceanfront Home" is around 2 miles northeast of Bailey Island and will be just the thing to refresh your spirit. You'll enjoy the range of amenities here, including a fridge and golf.
  • Alternatively, throw a few clothes in a bag and make a beeline for "Percival” Penthouse Suite: Breathtaking Views". This popular property is about 14 miles west of Bailey Island and has golf and a nearby marina.

Can I find studio apartments for rent in and around Bailey Island?

Studio apartments may be on the smaller side, but they pack a punch when it comes to location and convenience. Unpack your bags at one of these cozy studio apartments in and around Bailey Island:

  • One of our favorite properties is "Chic One Bedroom Apartment In Portland's Arts District". Lock in a few nights at this popular apartment and you'll have access to air conditioning and a pool.
  • Alternatively, use "Historic Condo With Casco Bay Views" as a base to tick off the best sights around you. This home away from home offers a microwave oven, an iron and ironing board and more.

Can I find short term rentals in or near Bailey Island?

From simple apartments to extravagant houses, Vrbo has your mini vacation sorted. Here are two of our most popular stays in and around Bailey Island:

  • Within close reach of central Bailey Island, "Percival” Penthouse Suite: Breathtaking Views" lays out the welcome mat for short-term guests. When you're not kicking back in your cozy digs, get out and discover all the fun stuff around you.
  • Alternatively, spend a few nights at "Margaret” Penthouse Suite: Amazing Views Of Casco Bay". This comfy, conveniently located property makes exploring the sights easy.

What are the best romantic weekend getaways in or near Bailey Island?

Whether spent in a log cabin or a beach house, a romantic weekend getaway is a perfect way to say "I love you." Whisk your sweetie away for a couple of days at one of these popular escapes in or near Bailey Island:

  • Sneak away on Friday for a couple of passion-filled nights at "Henry” Penthouse Suite: Amazing Views". Located roughly 14 miles from Bailey Island, this property comes with lots of nice touches, including winery tours and a nearby bay.
  • Another option where you can enjoy a few dreamy days together is "Chic One Bedroom Apartment In Portland's Arts District". Located around 15 miles from Bailey Island, a nearby bay and winery tours add to the atmosphere here.

What are the best large group vacation rentals in or near Bailey Island?

Sneak a peek at these large group vacation rentals in or near Bailey Island and don't worry about leaving anyone off your invite list:

  • Providing space, privacy and comfort, you'll get your guests' tick of approval at "New Well Built Elegant Home On The Water 2 Miles To Freeport". Up to 12 people can stay at this escape which has 6 bedrooms, an ocean view and a garden. You'll find it around 9 miles to the northwest of Bailey Island.
  • "Picturesque Seaside Cottage With Breathtaking Sunset Views On Bailey Island" is another impressive option. It's around 1 mile to the north of Bailey Island, has 2 bedrooms and sleeps up to 24 guests. A nearby waterfront and an ocean view are just a couple of things that'll help make your visit even more memorable.

What are the best houses for rent with a pool in or near Bailey Island?

Nothing screams fun like a pool does. Pull out your inflatable flamingo and browse these rental houses in or near Bailey Island that feature this vacation must-have:

  • Get comfortable at "The Beach House Bailey Island Maine", where your biggest priority will be hanging out by the pool. Amenities such as towels and a balcony help make this retreat a favorite with guests.
  • Spend laid-back days splashing around or finding some peaceful moments beside the water at "Spectacular Oceanfront House On Maine Coast". This vacation rental is another guest favorite and comes with a barbecue grill, nearby birdwatching activities and more.

Wondering what the weather is like in Bailey Island? It has a humid continental climate, with average temperatures in summer ranging from 60 ºF to 70 ºF. If you're searching for a little more inspiration on places to stay in this epic destination, use the search bar at the top of the page and adjust the filters to browse through our entire selection of Bailey Island vacation rentals.

What are the best large family vacation rentals in or near Bailey Island?

Whether your perfect escape is out in the countryside or on the beach, you'll have so much more fun if you share the experience with loved ones. Book one of these large family vacation rentals in or near Bailey Island and bring along the whole gang:

  • About 2 miles to the northeast of Bailey Island, "Maine Oceanfront Home" has 4 bedrooms and can sleep up to 11 guests. It comes with a host of amenities, including a separate dining area and coffee and tea making facilities.
  • "New Well Built Elegant Home On The Water 2 Miles To Freeport" is another excellent option. It's around 9 miles to the northwest of Bailey Island, has 6 bedrooms and can accommodate up to 12 guests. Handy amenities here include a TV and a DVD player.

If you want to do some sightseeing, there are loads of family-friendly attractions close by to put on your itinerary. Children's Museum of Maine, Portland Observatory and Fort Williams Park are excellent places to start.

Can I find family cabin rentals in or near Bailey Island?

Get away from it all and treat the people you love to a different kind of vacation. Stay in one of these family cabins in or near Bailey Island and get the camping experience — minus the tents and with all the creature comforts!

  • "Secluded Casco Bay Waterfront Cabin" - Located about 1 mile north of the center of Bailey Island, this family-friendly escape offers amenities like a fridge and a nearby bay.
  • "Renovated, Family Friendly Home With Ocean And Golf Views" - Another terrific option, this rental comes with childrens activities, a toaster and more. You'll find it around 7 miles to the east of Bailey Island.

For more options, use the search bar at the top of the page and adjust the filters to find the Bailey Island vacation rental that's perfect for your needs.