House vacation rentals in Bailey Island

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Popular amenities for Bailey Island house rentals

House rentals with a pool

Guest favorite
A community pool features a clear blue water surface, surrounded by a concrete patio with several white lounge chairs positioned nearby. Lush green trees are visible in the background, offering a sense of openness, while two buildings are situated just beyond the pool area.
Home in Old Orchard Beach
4.98 out of 5 average rating, 80 reviews

Faith Lane with community pool

MeghanRating, 5 stars7 months ago
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!
Guest favorite
A classic three-story colonial home with white siding and black shutters is framed by well-manicured shrubs and greenery. The symmetrical facade showcases a central entrance with a gabled roof, and warm light emanates from the windows, creating a welcoming appearance.
Home in Mechanic Falls
5 out of 5 average rating, 19 reviews

Lovely home with hot tub and pool

AngelicaRating, 5 stars6 months ago
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!
Top guest favorite
Home in Biddeford
5 out of 5 average rating, 27 reviews

Pool|HotTub|1Acr FencedYard|Firepit|Garden|PETS OK

AshleyRating, 5 stars7 months ago
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.
Superhost
A well-maintained pool surrounded by a neatly arranged garden with colorful flowers and greenery. The lawn extends into the distance, bordered by trees. A small shed is visible nearby, providing an additional outdoor feature.
Home in Washington
4.86 out of 5 average rating, 7 reviews

House in the woods

SavannahRating, 5 stars4 months ago
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!
Guest favorite
Home in Portland
4.95 out of 5 average rating, 122 reviews

"Good Vibes" 4 Wonderful Seasons @ Portland Home!

Kathleen AudreyRating, 5 stars2 weeks ago
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!
Guest favorite
A two-story home is presented, featuring a yellow exterior and dark blue shutters. A welcoming front porch is adorned with decorative elements. Lush green grass and various shrubs frame the entrance, while a driveway leads to a garage on the left side.
Home in Portland
4.82 out of 5 average rating, 109 reviews

There's No Place Like Home

JeremyRating, 5 stars6 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!
Superhost
The inviting living area features two light-colored armchairs with subtle blue accent pillows, a small decorative ottoman, and a side table with a lamp. A wooden staircase leads to the upper floor, while coastal-themed decor adds character to the space.
Home in Kennebunk
4.84 out of 5 average rating, 37 reviews

Kennebunk's Charming Beach Home

KylieRating, 5 stars4 months ago
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.
Superhost
The entryway features a welcoming front door with glass panels, flanked by two large planters with greenery. A wooden bench is positioned against the wall, providing a comfortable spot to sit. A welcome mat is placed at the entrance.
Home in Wells
4.88 out of 5 average rating, 24 reviews

Summertime Oasis with Inground Pool!

MelindaRating, 5 stars7 months ago
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

Top guest favorite
A dining area features a large round wooden table surrounded by several wooden chairs. A long wooden bench runs along one side of the space. Sunlight enters through multiple windows, highlighting the warm wood flooring and natural light atmosphere.
Home in Bridgton
5 out of 5 average rating, 19 reviews

Cozy Knights Hill Home

KellyRating, 5 stars1 month ago
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.
Guest favorite
The exterior of a two-story A-frame home is shown, featuring a dark blue facade. Two small balconies with white railings are visible on the second floor. The well-kept front yard includes neatly arranged shrubs and a pathway leading to the entrance.
Home in Wells
5 out of 5 average rating, 13 reviews

Wells Maine Year Round Rental

JerineRating, 5 stars1 month ago
great stay, had everything we needed and located in a central location for everything we did on our trip!
Top guest favorite
The dining area is visible through a doorway, featuring a round table surrounded by chairs. Natural light enters through a window, illuminating the space. A rocking chair is positioned nearby, and a decorative chair can be seen in the foreground, adding character to the room.
Home in Newcastle
4.96 out of 5 average rating, 45 reviews

Cozy & quiet on the river... the Captain's House

UtpalRating, 5 stars8 months ago
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.
Superhost
A spacious yard features a lush green lawn, surrounded by a wooden fence for privacy. Colorful flower beds are visible, with scattered seating options, including bright blue Adirondack chairs, inviting relaxation in the natural setting.
Home in Wells
4.88 out of 5 average rating, 34 reviews

2 BDR| Fenced in Yard| Hot Tub| Bring your pup

GeorgeRating, 5 stars6 months ago
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!
Top guest favorite
The exterior of a cottage is displayed, featuring a charming blue facade and a welcoming porch. White Adirondack chairs are positioned in the foreground, surrounded by a well-kept garden with colorful flowers. A shaded area is visible in the background with a sun umbrella.
Home in Biddeford
4.98 out of 5 average rating, 53 reviews

Hills Beach UNE 3-4 brs oceanview 50 steps 2 beach

LewisRating, 5 stars2 months ago
Fabulous; lovely place, close to the beach, good internet, nice amenities.
Guest favorite
A cozy living area is presented with a large arched window offering views of the outdoors. A small table is set for two, and colorful glass bottles are displayed above the window. Light hardwood floors complement the seating arrangement with plush chairs and a side table.
Home in Ocean Point
4.93 out of 5 average rating, 45 reviews

137 Shore Road Ocean Point view now with WiFi

ThomasRating, 5 stars6 months ago
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.
Guest favorite
A spacious chalet is set against a backdrop of lush greenery, featuring a combination of wood siding and large glass windows. A wraparound deck with seating provides outdoor space, while a screened porch adds an element for gear storage and relaxation.
Home in Bethel
4.96 out of 5 average rating, 50 reviews

Winter Park Lodge

BrianRating, 5 stars1 month ago
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!
Guest favorite
A serene view of a vibrant sunrise over the water, framed by leafless trees. Warm hues of orange and pink reflect on the calm surface, with silhouettes of distant trees enhancing the tranquil setting.
Home in Brunswick
4.98 out of 5 average rating, 50 reviews

Oceanfront, Mere Point year round home Brunswick

E ThomasRating, 5 stars7 months ago
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

Guest favorite
A waterfront cabin is presented with a metal roof reflecting sunlight. The front porch features seating arrangements, while a grassy area leads to the surrounding woods, enhancing the natural setting of the property.
Home in Liberty
4.98 out of 5 average rating, 87 reviews

Kirby Island Road Retreat

BlakeRating, 5 stars2 months ago
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!!
Guest favorite
A private driveway leads to a modern house with a red exterior and a silos-style structure. The property is framed by green trees and an expansive lawn, creating a welcoming entrance. Stone pillars with lanterns mark the beginning of the path.
Home in Wells
4.99 out of 5 average rating, 78 reviews

Beach Home w/ Exclusive privacy in Southern Maine

JordanRating, 5 stars2 months ago
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!
Guest favorite
A spacious yard features lush green grass and well-maintained landscaping. Two buildings can be seen: a gray cape-style home with multiple decks and a rustic structure. White outdoor furniture is positioned for relaxation, with trees providing a serene backdrop.
Home in Bremen
5 out of 5 average rating, 10 reviews

Authentic Maine Harbor 5 Bedroom Home

RandallRating, 5 stars6 months ago
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.
Top guest favorite
A light blue exterior of the building is presented, featuring white shutters and multiple windows. A wooden deck with steps leads to the entrance. The surrounding area includes white gravel, decorative items, and a small bench for relaxation.
Home in Wells
4.94 out of 5 average rating, 72 reviews

Beautiful House to Relax & Enjoy the Quiet!

NinoRating, 5 stars7 months ago
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!
Guest favorite
A serene outdoor space is bordered by trees and features a gravel area with seating around a fire pit. A wooden deck extends from the cabin, providing views of the nearby river, enhancing the natural landscape.
Home in Naples
4.99 out of 5 average rating, 116 reviews

LUX Designer Private Waterfront

ElliosRating, 5 starstoday
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!
Guest favorite
A comfortable living area is presented with a dark sectional sofa featuring beach-themed decor. A light-colored wooden coffee table is centered on a soft area rug, while decorative shelves and wall art enhance the coastal ambiance. Natural light streams through large windows, illuminating the space.
Home in Wells
5 out of 5 average rating, 26 reviews

Updated 2 Bedroom Private House near beaches

AnnemarieRating, 5 stars6 months ago
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!
Top guest favorite
A spacious living area is furnished with two leather couches and a coffee table, placed on a colorful rug. Large glass doors open to an outdoor space, allowing natural light to fill the room. A sleek kitchen is visible in the background.
Home in Yarmouth
4.92 out of 5 average rating, 532 reviews

Beautiful Coastal Maine Getaway

AmandaRating, 5 stars1 week ago
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!
Top guest favorite
A bright hallway features warm wooden flooring and a staircase leading towards a room bathed in natural light. A decorative star motif adorns the wall, and a small plant sits at the base of the stairs, adding a touch of greenery to the space.
Home in Portland
4.98 out of 5 average rating, 170 reviews

Modern & Sunny East End House. Private Parking!

MahasidhdhiRating, 5 stars1 week ago
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!

Destinations to explore

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  3. Maine
  4. Cumberland County
  5. Harpswell
  6. Bailey Island
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