
House holiday rentals in Bailey Island
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Top-rated house rentals in Bailey Island
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Popular amenities for house rentals in Bailey Island
House rentals with a pool

Treehouse Farm - Sebago
Great backyard with a pool, hot tub, fire pit and privacy with the woods.

Upscale OOB Beach House | Seasonal Heated Pool
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.

Lovely home with hot tub and pool
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.

"Good Vibes" 4 Wonderful Seasons @ Portland Home!
Angela was a fantastic host, responding quickly to any questions. The home was nice, close to downtown, and a HUGE yard for the dogs

There's No Place Like Home
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!

OOB Oasis - 5BR private Retreat w/ Pool
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!

Dreamy Indoor Pool/Hot tub/Sauna Near Beaches
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!

Pet Friendly Home, Ski Storage Room, HotTub, Sauna
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

Stunning Beachfront Dream Home
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!

Waterfront Cottage in Freeport
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!

Bluebell Cottage Beach Vacation
Would definitely stay here again. Was really a first class space that made our family feel very relaxed.

Oceanfront Luxury Estate in Mid-Coast Maine
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!

Captain's House near Henry Allen's Lobster Shack
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.

Maine Ocean Waterfront - Family, Rustic Getaway!
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!

Quiet Ocean View Cottage
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.

House 18 minutes to Popham 9 minutes to Bath
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

Great Island Oasis
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!

Amazing location! Cheerful home near LL Bean
Such a lovely, cozy spot! We stayed for two nights with toddlers and our dog and everyone was very happy there.

Whole house on a great island in Casco Bay!
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.

Close to Breweries, Outlets, and Portland Food!
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!

Waterfront |Near Mountains |Outdoor Sauna |Firepit
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.

Water views, privacy, decks, minutes to Portland
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 :)

Harbor Heights House
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!

Private Oceanfront Home 🔆2 min to Popham ✔️Hot Tub
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.
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- Ogunquit Beach
- Sebago Lake
- Wells Beach
- Scarborough Beach
- Popham Beach State Park
- Surfside Beach
- Pemaquid Beach
- Fox Ridge Golf Club
- Coastal Maine Botanical Gardens
- Cliff House Beach
- East End Beach
- Brunswick Golf Club
- Palace Playland
- Pemaquid Point Lighthouse
- Ferry Beach
- Funtown Splashtown USA
- Dunegrass Golf Club
- Parsons Beach
- Ogunquit Playhouse
- Laudholm Beach
- Wolfe's Neck Woods State Park
- Middle Beach
- Freddy Beach
- Crescent Beach State Park