Bailey Island Vacation Rentals

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Vacation Rentals in Bailey Island

Property grounds
PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room
10.0 out of 10, Exceptional, (94)
"We celebrated our Mom’s 70th birthday in this beautiful space. It exceeded our expectations and the property manager David is the best!"
PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room
Fridge, microwave, oven, stovetop
Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage
Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage
Exterior
Completely remodeled 2 bedroom apartment in Portland's West End
10.0 out of 10, Exceptional, (35)
"We very much enjoyed our stay at this location. The stairs were a bit scary, but with the light on, you'll be fine. :) Cozy spot for the three of us, well appointed and in a fantastic area. Very walkable, even down to the wharf. We are from a very non-walkable area, so it was amazing to see all the activity and places we could go just walking a bit. We enjoyed our first time in Maine, and can't wait to get back for a longer trip. Thanks to the hosts!"
The price is CA $314
CA $627 total
includes taxes & fees
Jun 13 - Jun 14
Completely remodeled 2 bedroom apartment in Portland's West End
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TV, fireplace
Delightful oceanfront home with amazing views, wrap-around deck & two fireplaces
8.8 out of 10, Excellent, (33)
"Great views. House pretty clean & supplies were fine except only 3 coffee cups for 6 adults. VACasa said they would get more cups. They failed, never received. Some lights didn't work & lots of dead bugs in light fixtures."
Delightful oceanfront home with amazing views, wrap-around deck & two fireplaces
Property grounds
Artsy Apt/Private Rooftop Deck!/Old Port Arts Dist
10.0 out of 10, Exceptional, (16)
"Excellent apartment in Old Port area of Portland. Bright, clean, updated, comfortable bed and furniture, lots of amenities. Would definitely stay there again!"
Artsy Apt/Private Rooftop Deck!/Old Port Arts Dist
Exterior
Rent a room in the gorgeous Holt House
8.4 out of 10, Very good, (19)
"It was a great trip up to Portland and the property met our needs."
Rent a room in the gorgeous Holt House
View from property
Popham Beach Direct Oceanfront Cottage Steps to the sand
10.0 out of 10, Exceptional, (44)
"We had a great stay. Check in and communication was easy. Due to storm damage, our original booked cottage was not available and Deb offered us a different (much larger) home without added cost. We greatly appreciated it so we didn't have to cancel our vacation. The home was very clean and had everything we needed and then some. The area is beautiful and the beach was very clean. You cannot beat the views from the home. We look forward to staying here again!"
Popham Beach Direct Oceanfront Cottage Steps to the sand
Interior
Unique oceanfront home with a deck, tons of natural light, & amazing views
8.8 out of 10, Excellent, (43)
"We needed a quiet place to visit with elderly aunt and uncle. This was a great place with all the living space on the same floor with spacious area to visit."
Unique oceanfront home with a deck, tons of natural light, & amazing views
Fridge, microwave, oven, stovetop
Full sized home
9.4 out of 10, Exceptional, (3)
"It was a nice little house"
The price is CA $342
CA $470 total
includes taxes & fees
May 26 - May 27
Full sized home
1 bedroom, WiFi
Quaint one-bedroom suite
9.8 out of 10, Exceptional, (38)
"Quiet peaceful great accommodations and wonderful host"
The price is CA $137
CA $194 total
includes taxes & fees
May 26 - May 27
Quaint one-bedroom suite
2 bedrooms, cribs/infant beds, internet, bed sheets
Inviting apartment with full kitchen, porch, convenient location, & fast WiFi
7.0 out of 10, Good, (6)
"This home was clean, bright and comfortable. Great location, no issues. Would definitely stay here again."
Inviting apartment with full kitchen, porch, convenient location, & fast WiFi
Private kitchen
Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants
9.8 out of 10, Exceptional, (88)
"We were in Portland for my daughter’s graduation. Had a very nice weekend trying different restaurants and enjoying lobster rolls."
Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants
Fridge, microwave, oven, stovetop
Cozy, Elegant and Bright 2 bed in the East End
10.0 out of 10, Exceptional, (26)
"This was our first time in Portland, and the location was perfectly suited for us to see everything! We were able to walk to restaurants and a little market around the corner. The home was easy to access and we were always able to find a parking spot. The unit itself was really nice, although the living room did not have enough seating for our travel party (four adults; there was a couch that technically could fit three people but not comfortably). The unit was very clean and there were plenty...
The price is CA $274
CA $503 total
includes taxes & fees
May 27 - May 28
Cozy, Elegant and Bright 2 bed in the East End
Private kitchen
Elegant condo - walk to Portland's best restaurants & Old Port
9.4 out of 10, Exceptional, (45)
"The kitchen was very well equipped. Living room was so cozy with the fire. Bed was super comfortable. The unit has really tall ceilings and is cozy. Only issue was the dog upstairs. They kept barking and whining."
Elegant condo - walk to Portland's best restaurants & Old Port
TV, fireplace, books, stereo
Appalachee Pond Waterfront Cottage | Decks, Sunroom, Dock with Kayaks & Canoe
9.4 out of 10, Exceptional, (23)
"Beautiful home that is a great proximity to Boothbay Harbor downtown. The pond is very nice but the water level was very low during our stay in March and there were no boats available as described in the listing. It is unclear whether this is something to note for all offseason travelers"
Appalachee Pond Waterfront Cottage | Decks, Sunroom, Dock with Kayaks & Canoe
Fridge, microwave, oven, stovetop
Stunning oceanfront cottage w/ private deck and Atlantic views
9.2 out of 10, Wonderful, (37)
"The view was exceptional "
Stunning oceanfront cottage w/ private deck and Atlantic views
Aerial view
Ocean view Victorian
9.8 out of 10, Exceptional, (73)
"It was the best view of Casco Bay and such a unique home. Beautiful accommodations that are both historic yet updated for comfort and convenience. Our host was phenomenal! So friendly…we thought he was one of our neighbors from Louisiana (not just because of his homemade hot sauce that he sent home with us, but more importantly because of his hospitality!)"
Ocean view Victorian
Fridge, microwave, oven, stovetop
Private Oceanfront Home on 10 Acres -- 2 Fireplaces, 4 Decks & Grill
8.8 out of 10, Excellent, (12)
"My family and I loved this place so much that we definitely want to come back and stay again. Beach combing was fun looking for interesting rocks and seaglass. It was also nice sitting out the huge rocks and admiring the water. Driving around the town of Boothbay was amazing. The people were so friendly and the town has alot of charm. The house was another part of the trip that made it memorable. It had plenty of windows to be able to get a view of the water. The house was well equipped and the...
Private Oceanfront Home on 10 Acres -- 2 Fireplaces, 4 Decks & Grill
Property grounds
Charming 110-year former Inn 10' from the Ocean!
9.8 out of 10, Exceptional, (99)
"Lovely home in a beautiful location. Very welcoming, cozy, and friendly. Easy check-in and check-out process. The owner was very accommodating and helpful. Made amazing memories and look forward to returning soon. Thank you so much!"
Charming 110-year former Inn 10' from the Ocean!
Property grounds
Glorious getaway on Portland's Eastern Promenade.
10.0 out of 10, Exceptional, (124)
"We really enjoyed our stay. We loved being able to walk to the Eastern Promenade. The beds, including the sofa bed were very comfortable. Very cute and cozy There are stairs to enter the building for anyone with mobility issues. If you are unfamiliar with older buildings, the radiators do make some noise while heating in the winter."
The price is CA $392
CA $624 total
includes taxes & fees
May 27 - May 28
Glorious getaway on Portland's Eastern Promenade.
Don't see what you're looking for?
See all available properties in Bailey Island
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other types of properties in Bailey Island you may be interested in

Water view
The Westin Portland Harborview
4.0 star property
8.6 out of 10, Excellent, (1054)
"Excellent TV screen and easy channel options."
The price is CA $220
CA $251 total
includes taxes & fees
May 27 - May 28
The Westin Portland Harborview
Honeymoon Suite, 1 King Bed
Portland Harbor Hotel
4.0 star property
9.0 out of 10, Wonderful, (1196)
"One of the best hotels we ever stayed in."
The price is CA $282
CA $360 total
includes taxes & fees
May 27 - May 28
Portland Harbor Hotel
Lobby
Casco Bay Hotel, Ascend Hotel Collection
3.5 star property
8.6 out of 10, Excellent, (1501)
"All good"
The price is CA $122
CA $133 total
includes taxes & fees
Jun 9 - Jun 10
Casco Bay Hotel, Ascend Hotel Collection
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Bailey Island. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a vacation rental in Bailey Island?

Yes, we give you a choice of vacation rentals in Bailey Island near Land's End Gift Shop, or you can choose a secluded option if you're looking for extra privacy while you relax. Bailey Island is known for its shopping and seafood restaurants. Make sure you have time to check out the local tours and monuments during your trip.

What are some of the best vacation rentals that Bailey Island has to offer?

Stunning oceanfront cottage w/ private deck and Atlantic views: This vacation home rental outside of Bailey Island is located on the beach and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals are there in Bailey Island?

With 29 Expedia vacation rentals, you're sure to find just the right place for your Bailey Island stay.

What can I see and do in Bailey Island?

Family-friendly attractions include Land's End Gift Shop, whereas Ragged Island is a spot to enjoy the outdoors. Bailey Island Bridge and Cobwork Bridge are other places to visit while you're in town.

What are vacation rentals like in Bailey Island?

Vacation rentals are private properties you can reserve for several days or longer in Bailey Island. Vacation rentals feature amenities such as patios, hot tubs, and fire pits so you'll have a home away from home. If you're concerned about a clean environment, vacation rentals can offer a sense of safety away from shared hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive choice for a small group gathering.

Recent reviews of Bailey Island properties
Expedia verified reviews

Holiday Inn Portland-By the Bay, an IHG Hotel

Holiday Inn Portland-By the Bay, an IHG Hotel

5/5 Excellent
Recommend, great stay
"Great stay, the staff were very friendly and helpful. Clean, comfortable. The only thing I wish had been better was the breakfast. It was a buffet but they didn't have toast. There were some muffins left and scones. Maybe there would have been toast earlier in the morning but I didn't see a toaster either. I ended up asking for hot water to make oatmeal I had brought. I'm also a picky eater though so for everyone else it seemed fine. I just like my toast in the morning. "
A verified traveller stayed at Holiday Inn Portland-By the Bay, an IHG Hotel
Posted 21 hours ago
Holiday Inn Portland-By the Bay, an IHG Hotel