House holiday rentals in Bailey Island

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Popular amenities for house rentals in Bailey Island

House rentals with a pool

Guest favourite
Home in Sebago
5 out of 5 average rating, 18 reviews

Treehouse Farm - Sebago

HollyRating, 5 stars1 month ago
Great backyard with a pool, hot tub, fire pit and privacy with the woods.
Guest favourite
Home in Old Orchard Beach
4.98 out of 5 average rating, 41 reviews

Upscale OOB Beach House | Seasonal Heated Pool

BonnieRating, 5 stars1 week ago
This was the perfect home base for exploring various parts of the Maine coast. Beds were comfy, and each room had a wall unit to make it the temperature you like. Our kids loved being upstairs in the 3 beds room and having their own space. WiFi worked great, and that was with 7 of us on it doing various things - adults working, kids streaming. Would definitely stay here again.
Guest favourite
Home in Mechanic Falls
5 out of 5 average rating, 20 reviews

Lovely home with hot tub and pool

ErnieRating, 5 stars2 days ago
I had a wonderful stay., they were fantastic in accommodations for me and my service dog who loved the yard. The home is beautiful and the host was very accommodating. communication was great. I look forward to staying there when I’m in that area again.
Guest favourite
Home in Portland
4.95 out of 5 average rating, 128 reviews

"Good Vibes" 4 Wonderful Seasons @ Portland Home!

MatthewRating, 5 stars1 week ago
Angela was a fantastic host, responding quickly to any questions. The home was nice, close to downtown, and a HUGE yard for the dogs
Guest favourite
Home in Portland
4.82 out of 5 average rating, 110 reviews

There's No Place Like Home

JeremyRating, 5 stars8 months ago
Kathi’s place was great! Super close to the Downtown Portland/Old Port area. Kathi was a great host, extremely responsive and genuinely nice, plus she even made my family and I some delicious blueberry muffins for our stay! Her instructions were clear and she made us feel right at home! Would definitely stay again whenever we’re in the area!
Top guest favourite
Home in Old Orchard Beach
4.96 out of 5 average rating, 109 reviews

OOB Oasis - 5BR private Retreat w/ Pool

JohnRating, 5 stars1 month ago
Great house! Very spacious, plenty of bathrooms, and fantastic location. Very easy to communicate with the owners and check in/out was simple. My minor only critique is that we wish the grill were a bit bigger and nicer. We wanted to grill one day, but we were a little disappointed and unable to do so due to the grill quality. Would definitely stay again!
Top guest favourite
Home in Scarborough
5 out of 5 average rating, 15 reviews

Dreamy Indoor Pool/Hot tub/Sauna Near Beaches

Lisa-MarieRating, 5 stars1 week ago
Top notch spot and host!! We had such a great time at Alexa’s lovely home! It was so cozy, beautifully decorated, modernized, and had all the essential items you’d need - plus it is completely pet friendly! Our dog loved the fenced in yard with a doggy door to get out to it. The sauna, endless pool, and hot tub are just amazing amenities to have on site - that sunroom was my favorite place in the house to say the least! Can’t say enough about it and Alexa, too! She is super friendly, responsive, and had great recommendations for fun and good food in the area. Overall, it was just a wonderful and relaxing experience for our first time on the Maine coast and we can’t wait to visit again!
Top guest favourite
Home in Bethel
5 out of 5 average rating, 17 reviews

Pet Friendly Home, Ski Storage Room, HotTub, Sauna

JamesRating, 5 stars3 weeks ago
This place was one of the best i’ve stayed in, and Joe & Colleen thought of everything you could possibly need to feel beyond comfortable. They were extremely kind and responsive hosts, and the space made us feel like royalty. What a fantastic experience, better than the pictures, we never wanted to leave the home. We enjoyed walking the neighborhood with our dogs, and did i mention the hosts left dog bowls, beds, toys, waste bags and more? This home is less than 10 mins from bethel village, 15 from sunday river, and 20 from beautiful grafton notch state park. Overall, the house was amazing, the sauna hot tub and heated pool were fantastic, and we would stay again in a heartbeat

Weekly house rentals

Top guest favourite
Home in Old Orchard Beach
5 out of 5 average rating, 20 reviews

Stunning Beachfront Dream Home

Marie-SophieRating, 5 stars1 week ago
This beach house was an absolute dream. Perfectly located just steps from the ocean, with tons of natural light and beautiful design throughout. It felt like a true home away from home - peaceful, airy and well equipped with everything we needed. We couldn’t have asked for a better stay. Highly recommend, we will be back!
Top guest favourite
Home in Freeport
5 out of 5 average rating, 47 reviews

Waterfront Cottage in Freeport

BrianRating, 5 stars3 weeks ago
Beautiful location on the water with stunning views, tranquil and peaceful with plenty of osprey and bald eagle sightings (there is a nest across the bay on Pettingill Island visible from the property). The house is very well-appointed and well-decorated. Irena was very communicative and responsive, and the house directions are clear and complete. We would stay there again. Thank you!
Top guest favourite
Home in Biddeford
5 out of 5 average rating, 5 reviews

Bluebell Cottage Beach Vacation

KeithRating, 5 stars2 weeks ago
Would definitely stay here again. Was really a first class space that made our family feel very relaxed.
Superhost
Home in Harpswell
5 out of 5 average rating, 36 reviews

Oceanfront Luxury Estate in Mid-Coast Maine

SharonRating, 5 stars9 months ago
This was such a wonderful property for my family -- beautiful and peaceful with lovely views. We loved spending our days out in the spacious yard, playing lawn games, sitting around the fire pit, and fishing, and eating all our meals out on the patio. Everyone left feeling very relaxed and happy. Thank you Pam and David for sharing your home!
Guest favourite
Home in Harpswell
4.8 out of 5 average rating, 55 reviews

Captain's House near Henry Allen's Lobster Shack

EvantheRating, 5 stars1 week ago
What a gem this home will be as Kate continues to transform it - loved reading about its history and trying to figure out its origins. The instructions were super detailed, and everything was as described - clean and tidy. The home is in a peaceful area, friendly neighbors, and we loved being able to have the windows open to hear the birds, frogs, and roosters. We were only 15 mins away from Brunswick proper, and Kate gave some awesome recommendations on where to grab a bite and what to go see.
Guest favourite
Home in Harpswell
4.94 out of 5 average rating, 54 reviews

Maine Ocean Waterfront - Family, Rustic Getaway!

AndrewRating, 5 stars1 week ago
Chip was an amazingly gracious and friendly house, with a house to be a great place for a true Maine Vacation! With amazing views and tons of great recommendations and information from Chip, it made our trip top notch. With plenty of yard space, amazing views over Casco Bay and sunsets that you could only dream of, this place really highlights why Maine is my little slice of heaven. Chip’s very detailed instructions made our stay amazing and helped us out immensely! With no shortage of sites or things to do, this is a great place for your next vacation!
Guest favourite
Home in Brunswick
4.85 out of 5 average rating, 60 reviews

Quiet Ocean View Cottage

LisaRating, 5 stars8 months ago
Very nice rustic cabin, convenient location to Brunswick. Our stay was in mid-October, and we knew there was no heat, only space heaters - unfortunately got into the low 30s at night and we were very cold. Grateful for the many blankets! The two beds are not full twins, more like 24” beds; it was ok for our small teenager. Well water. Nice location and would go back in warmer weather! Very responsive host.
Superhost
Home in Phippsburg
5 out of 5 average rating, 5 reviews

House 18 minutes to Popham 9 minutes to Bath

TylerJaikRating, 5 stars6 days ago
This place has all the comforts of home and then some. Very thoughtful amenities including a smart TV, a turntable with a small eclectic vinyl collection, and indoor and outdoor games. Every room having lightswitches with dimmers and the separate climate control units in each bedroom were great! With beach gear available for a quick drive down to Popham and being able to bring the outdoors indoors by opening up the two retractable doors on the first floor were fantastic! Alina and Brian are very communicative and accommodating. We will certainly be staying here again for our next trip.

Private house rentals

Top guest favourite
Home in Harpswell
4.94 out of 5 average rating, 34 reviews

Great Island Oasis

ElenaRating, 5 stars2 weeks ago
Stayed here with a big group for a college reunion. Rob was communicative leading up to the visit. The house is spacious and in great shape, with charming touches--lots of pottery! I have dust allergies and had no issues in the upstairs bedroom I stayed in. The grounds are immaculate and big enough for lawn games and a fire pit. Keep driving down the road to Orr's and Bailey's islands. Amazing ocean views down there, and just a short 10-15 minute drive to Brunswick for great restaurants. Try The Abbey for coffee and cocktails!
Superhost
Home in Freeport
4.8 out of 5 average rating, 35 reviews

Amazing location! Cheerful home near LL Bean

EmilyRating, 5 stars8 months ago
Such a lovely, cozy spot! We stayed for two nights with toddlers and our dog and everyone was very happy there.
Top guest favourite
Home in Long Island
4.98 out of 5 average rating, 65 reviews

Whole house on a great island in Casco Bay!

AnneRating, 5 stars3 weeks ago
We love Long Island and the view from Nona’s View was phenomenal! The house was clean and tidy and had everything we needed! Bridget was extremely responsive and we would go back for another visit in a heartbeat.
Top guest favourite
Home in Yarmouth
4.97 out of 5 average rating, 100 reviews

Close to Breweries, Outlets, and Portland Food!

AnnieRating, 5 stars3 days ago
We booked Will’s place last minute and it turned out to be the perfect spot to relax for an evening! Nice neighborhood and close to amenities! Cute house with great Maine coastal decor. Would definitely stay again!
Top guest favourite
Home in Sweden
4.99 out of 5 average rating, 84 reviews

Waterfront |Near Mountains |Outdoor Sauna |Firepit

KJRating, 5 stars1 week ago
One of the best Airbnb experiences! The location and surroundings were absolutely beautiful, and the house was exceptionally clean and comfortable. We had the chance to fish and kayak, which were the highlights - so peaceful and scenic. This was a truly unforgettable experience. We caught a couple of bass and pike, which was so much fun. The host was also very responsive and kind. We will definitely come back and highly recommend this place.
Top guest favourite
Home in Cumberland
4.98 out of 5 average rating, 56 reviews

Water views, privacy, decks, minutes to Portland

JamaRating, 5 stars1 week ago
What a beautiful spot for a lovely weekend with friends. We enjoyed the contrast of exploring Portland, with the 15 min. escape back to this peaceful and beautiful home. This spot has everything you need, is comfortable for a group, and allows you to soak up the natural surroundings and space without being too much of a car ride away from the amazing city that is Portland. Would definitely stay again or even move in if I could :)
Superhost
Home in Harpswell
4.92 out of 5 average rating, 50 reviews

Harbor Heights House

TrentRating, 5 stars2 months ago
Wonderful home in a remote, beautiful and peaceful area. Half a dozen off leash hiking trails within 10 miles so my lab also enjoyed the month-long stay. Thank you Robin and Darren!
Guest favourite
Home in Phippsburg
4.97 out of 5 average rating, 88 reviews

Private Oceanfront Home 🔆2 min to Popham ✔️Hot Tub

PeggyRating, 5 stars3 weeks ago
We loved staying at this cabin near Popham beach, the house was beautifully renovated. The renovation kept the cabin feel, yet at the same time felt updated and modern. I'd stay there again in a heartbeat.

Destinations to explore

  1. Airbnb
  2. United States
  3. Maine
  4. Cumberland County
  5. Harpswell
  6. Bailey Island
  7. House rentals