
House vacation rentals in Bailey Island
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Top-rated house rentals in Bailey Island
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Vacation rentals for every style
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Popular amenities for Bailey Island house rentals
House rentals with a pool

Faith Lane with community pool
Beautiful house! Lots of space and had everything you need for your visit. The community pool was great too. Very close to Portland and easy to get to other areas of Maine from the location. Jason was a great host and very responsive and helpful! Only minor complaint was mattresses upstairs were a little on the firm side but other than that the house was great!

Lovely home with hot tub and pool
Beautiful Airbnb! Everything in the Airbnb was very well thought out. The host was super nice and always quick to respond. My only regret was not spending more time here!

Pool|HotTub|1Acr FencedYard|Firepit|Garden|PETS OK
Thank you for allowing us to stay at your beautiful home. The photos did it no justice! I can’t wait to be back, we will be stay here again.

House in the woods
Booked this place for our anniversary to get away from the city for a weekend.. we found exactly what we were looking for! The hot tub was wonderful, the house was clean and cute, and we had everything we could have needed! Estelle was very responsive and gave clear instructions for everything. Would recommend this place for a quiet getaway or a small group trip in the summer!

"Good Vibes" 4 Wonderful Seasons @ Portland Home!
My stay was very comfortable. The property was well kept and updated. The beds and furniture were were in perfect condition. Both the house and the grounds were exceptionally clean and well maintained. I would visit again!

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!

Kennebunk's Charming Beach Home
We had a wonderful stay for Christmas, we were even allowed to bring our fur baby! The home was beautiful with all of the amenities we could hope for.

Summertime Oasis with Inground Pool!
Great place to stay for a big family and kid-friendly! We had a fantastic trip and the host was super responsive. The living room area is even more beautiful in person. Highly recommend this place.
Weekly house rentals

Cozy Knights Hill Home
We had a great stay at the house. Chris and Nadine were very responsive and helpful with information. The house is so comfortable in terms of layout and has everything you need. We enjoyed sitting by the fire and relaxing at the end of the day. Would highly recommend this home if you are staying in the area.

Wells Maine Year Round Rental
great stay, had everything we needed and located in a central location for everything we did on our trip!

Cozy & quiet on the river... the Captain's House
The hosts were very prompt in communicating. The thoughtfulness they have put into furnishing the property is amazing. It has a very vintage nautical feeling to it. The house is extremely well appointed. We didn’t have any problems at all. The surroundings are off the beaten path which we especially appreciated. It’s a short 10 minute drive to Damariscotta Downtown. I would highly recommend this property.

2 BDR| Fenced in Yard| Hot Tub| Bring your pup
Actually rented both units A & B of this property for my wife's birthday to have some room for additional family (surprise). Unit A was awesome! 2 beds and a bath, BIG kitchen that had everything you would need, dog friendly with a fenced in yard which is always a plus, super comfortable living room/dining room combo that had plenty of room for everyone to gather, private courtyard (shared with unit B) with room for outdoor dining and a grill PLUS hot tub! I could go on but to summarize, it was perfect for our plans. The addition of unit B gave us the whole place and I couldn't be more pleased! Centrally located. Anywhere we wanted to explore, from Kennebunkport to Ogunquit and beyond, was never more than 20 - 30 minutes away. Even the neighbors were amazing (friendly)! 100% I would (and plan to) stay here again!

Hills Beach UNE 3-4 brs oceanview 50 steps 2 beach
Fabulous; lovely place, close to the beach, good internet, nice amenities.

137 Shore Road Ocean Point view now with WiFi
Jerry's house was a great location with terrific views. The house was tastefully decorated and immaculate. A perfect Maine getaway that we cannot wait to go back to in the future.

Winter Park Lodge
Maine Ski Lodging was great - we had a few general questions and they were very quick to respond! The home was very nice - beautiful deck and view - house was very clean! Pool table in finished basement we used a lot - TV's worked great and easy to use. Beds were very comfortable - plenty of dishes/glasses and we used pots, pans, strainers - nothing lacking in the kitchen. Hot tub after skiing worked out great! Would rent here again!

Oceanfront, Mere Point year round home Brunswick
Loved the layout of the house. Great kitchen and master bedroom. Master bath a little cramped. Enjoyed the view and outdoor seating.
Private house rentals

Kirby Island Road Retreat
Loved staying at this cabin! I was a last minute booking and the hosts were super nice and accommodating. Would recommend these hosts and this cabin to everyone!!

Beach Home w/ Exclusive privacy in Southern Maine
We had a wonderful time in Wells! An absolutely beautiful home with every amenity! Sharon was responsive, kind, and flexible with our stay. We enjoyed cooking and watching the Super Bowl in the amazing home theater! Do not miss out on this fantastic listing!

Authentic Maine Harbor 5 Bedroom Home
The house was exactly what we were looking for: relaxing with great views. The marina with fresh seafood within walking distance was icing on the cake.

Beautiful House to Relax & Enjoy the Quiet!
We had a wonderful stay. The house was very nice and all accommodations were met and exceeded. We cooked dinner in the kitchen two of the nights we were there and found everything we needed very easily. Everything was very clean and well taken care of, yet felt extremely homey and welcoming! The fire pit and outdoor bar were an amazing benefit, the whole back/front yards and patios in general were amazing. It’s safe to say we truly enjoyed our time in this home and will be checking here first next time we come! Highly recommended stay!

LUX Designer Private Waterfront
Jon’s space was very clean, private, and presented a “wow” factor in every direction I turned. Very well thought out; a truly transformative experience!

Updated 2 Bedroom Private House near beaches
We had a great stay in Tara's home. It is located in a quiet neighborhood and is close to our favorite towns- Ogunquit and Kennebunkport. We had plenty of room for the four of us. We loved the outside spaces and the open floor plan. Tara was very easy to communicate with and very responsive. The instructions for check in and check out were very clear. We hope to return in the future!

Beautiful Coastal Maine Getaway
Beautiful house that actually felt like a home! Randy was also very helpful and responsive. Kitchen and bathrooms were well stocked with everything we needed. Great experience overall!

Modern & Sunny East End House. Private Parking!
Our family of four thoroughly enjoyed our stay at Jennifer’s! She was so kind to provide a pack & play for our baby and send over a long list of family friendly restaurant recommendations. We used many of her suggestions. Very comfortable stay in a beautiful sunny home!
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- Wells Beach
- Ogunquit Playhouse
- East End Beach
- Surfside Beach
- Fox Ridge Golf Club
- Brunswick Golf Club
- Popham Beach State Park
- Parsons Beach
- Portland Museum of Art
- Mothers Beach
- Ferry Beach
- Pemaquid Beach
- Coastal Maine Botanical Gardens
- Cliff House Beach
- Dunegrass Golf Club
- Palace Playland
- Funtown Splashtown USA
- Laudholm Beach
- West Shore Sandy Beach
- Arundel Beach
- Crescent Beach State Park
- Wolfe's Neck Woods State Park
- Pemaquid Point Lighthouse
- Western Beach