
Family-friendly holiday rentals in Islesboro
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Top-rated family-friendly rentals in Islesboro
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Popular amenities for Islesboro family-friendly rentals
Family-friendly home rentals with a hot tub

Raven's Crossing - Kate's Cottage
Lori’s is exactly what we need while visiting family over a holiday. She is very gracious to host us over Thanksgiving as the last occupants of the year. Even during a snow storm, her place is cosy and beautiful. This is our second year coming, and we love it every time. We would recommend it for those looking for a charming getaway from busy life. Thanks Lori!

Latham Blueberry Farm for up to 6 guests.
We couldn’t have asked for a better stay at Latham blueberry farm. Doug and Brenda were incredibly helpful and friendly- they introduced us to the house and farm as soon as we checked in and were always available if needed. The beds were comfy, the kitchenette stocked, and the grounds were gorgeous. Their beautiful 1826 farm house was an authentic experience of staying on a farm- our kids loved feeding the animals (especially Ernie the pig and Moses the horse); picking fresh blueberries; and swimming and paddleboating in the private pond. Our hosts had great recommendations for local outings, and we loved chatting with them and playing with their puppy Jackie. Our family made lifetime memories.

Amazing view, eagles, hot tub, 1 mi walk from Bath
We really enjoyed our stay at Woolwich. There is a peaceful nature vibe to the house and a beautiful view and location. The Bald Eagles live in a tree right on the edge of the backyard and were visible numerous times during our stay. The location to various towns and locations in Maine is convenient.

Central Chalet
I gotthis as a vacation for my parents. They lived it H even brought their dog who also had a great time.

Tree Dwelling with Water Views & Cedar Hot Tub (2)
We had the most amazing stay at Madawaska! Amazing views from the bedroom and hot tub in a beautiful, peaceful, and private location overlooking the water. And such a wonderful design of the cabin. We will definitely be back!

Cozy hot tub haven
Great place. The bed was really comfortable. Hot tub was nice and private and relaxing.

Nashport on the Penobscot
This was our second time staying here, my family and I love the tranquility of this little piece of heaven. Christopher’s home was beautiful, clean and well maintained.

Oceanfront Loft with gorgeous water views & beach!
We had an amazing stay here! The loft was spacious and comfortable. The property was gorgeous - we went down to the beach area for a sunrise which was lovely! It was a quick drive to the main area of Lincolnville and to Camden which were both really cute. Lots of great food in the area too - Kate gave some great restaurant recommendations! Would definitely return to this Airbnb if we visit the area again!!
Family- and pet-friendly home rentals

McKeen's Riverside Retreat
We have stayed at Jackies place twice now and enjoyed it just as much this time as the last. Even though it rained for two days the house is plenty big enough to spread out. We had to change our reservation days twice because of circumstances and Jackie was very accomidating..

Plovers Cottage, Waterfront
This was hands down the best place we have ever stayed both on AirBnB and through other platforms. Mark & Kathy were so incredibly kind. The house is private with stunning water views and so clean and comfortable. The home was truly amazing. I can’t say enough about this place and the hosts. Everything was perfect and while we typically go somewhere new every travel, this has us already thinking about coming back just to enjoy it again! It’s close to Acadia though with how busy Acadia is I recommend visiting Schoodic Peninsula and the other preserves in the area. Sunset here was spectacular.

Lakefront, near Bar Harbor, ME
A great stay at this lovely, cozy home—yet again! Already looking forward to returning in July. You’ll find it all here: It’s quiet, with all the amenities you need (and nothing you don’t), the pretty water views, and a location that provides access to good restaurants and the beautiful Acadia National Park.

Rustic Family Cabin on China Lake
I loved this place! Enjoying coffee and meals outside on the deck overlooking the lake and beautiful surroundings of nature. I felt safe there and was a charming neighborhood. I loved that there were boats to use and a dock to watch sunset an autumn harvest moon over lake! Jess was the perfect host and made sure everything was great when I arrived. She was very helpful when I had any questions and I am looking so forward to going back there again! Thank you Jess for sharing this wonderful place!!!

Peaceful Branch Lake Cabin minutes to Acadia
It was just great, wish we stay longer, and we will definitely be coming back, we hope to book for longer and I think we would like to come back in the summer months. Acadia was beautiful, we were able to use the canoe and go into the lake, set up a fire, and make s'more.

CLEAN, spacious, each BR has private full bathroom
We are a family of five with three teens. The space was perfect for us to all hang out together and play a board game at the dining table, as well as spread out and have plenty of down time in our own rooms. I thought it was a nice touch that the front door was open and the keys were in the kitchen. Great to have bathrooms in each of the rooms. When we were planning our trip, we weren't 100 percent sure if our pet care person was going to be available, and Sarah was very responsive and flexible with us asking if we could add our dogs at the last minute. We didn't need to bring them, but it was so helpful to know that we could. We bot a huge box of pastries from Clark Point Cafe, and we would have gone back and sat down for a full breakfast if they had been open on our second morning. I guess that gives us an excuse to come back! The back yard view is private and beautiful. So much to like about our stay. Hard to fit it all in here. Thanks to Sarah and her family for everything.

Long Cove Artist Cottage
This cabin was a wonderful place to spend the week, and I couldn’t be more happy. The hosts were communicative and friendly; offering great local recommendations. My girlfriend and I would be more than happy to stay here again!

Rustic Farmhouse at Oxbow Brewery
We loved our stay at the guesthouse! We were pleasantly surprised by the amount of space and it was pretty magical having the beautiful grounds to ourselves on the day the brewery was closed. Except of course for Dizzy, who provided ample comic relief throughout our stay! Not unexpected for the area, but we did need to be super vigilant about ticks - they were out in force even in April. Otherwise we absolutely recommend staying here.
Family-friendly home rentals with a pool

Riverside home in Central Maine near Colleges
Great 2-level apartment with terrific deck and beautiful view overlooking the river. Quiet and pretty. Owners were very responsive and the kitchen is very well stocked. Nice rustic touches and great running/walking trail along the river, just down the road. WiFi works well. Recommend upgrading the beds as they are small and not very comfortable. Otherwise a great property!

Large Home with Great View next to horse farm
Great house and good location, it was warm during our stay. Enough space for our company. Not far away from the city. Overall it was nice staying there.

Luxury Condo on Water's Edge in Boothbay Harbor
A few times while wandering around midcoast Maine in late March, we were asked if this is when we usually came to vacation here. Yes, we are educators from the Southwest, and this was our spring break, so this is when we came to visit, but honestly, it is so peaceful this time of year. Especially Boothbay Harbor, and what we imagined while walking around the very quiet town would be a very different place in July! Our experience at Abby’s space was absolutely wonderful and serene in the spring. The thoughtful touches (thank you for the bottle of Maine wine and jar of blueberry jelly!) made it even more special. Thank you, we hope to be back one day.

Tremont, ME. Shorefront compound for 7-12
Three girlfriends and I stayed at Hillside for a week. The setting and location were absolutely beautiful. It was so quiet and peaceful and I loved walking the trail. The house was roomy and comfortable. We highly recommend!!

The Point, At The Edge Of The Ocean
Our stay here was amazing, the house is adorable and the views are stunning. The pool was the perfect temperature and the whole family was in the pool every day, plus the views from the pool were pretty remarkable. Sherri was a great host and super communicative and helpful. The house is set up perfectly for a large group with cute little restaurants a short car ride or boat ride away. We will definitely be back!

Harbor Ridge Resort - Southwest Harbor, ME
Worked great for our family of six. Comfortable and quiet unit. Pool and hot tub on premises were a big plus for the kids. Would be happy to return in future years.

Samoset Resort Oceanfront Condominium 816
Laurie was super communicative and the condo was GREAT! Had view of water, was clean and lots of space. Lots to do on the property with kids /teens: basketball court, volleyball, tennis, golf and more. The weather was not terrific, but between the heated pool, the activities and the closeness to Camden, there was lots to do.
Quick stats about holiday rentals that are family-friendly in Islesboro
Total rentals
140 properties
Nightly prices starting at
£60 before taxes and fees
Total number of reviews
2.9K reviews
Pet-friendly rentals
60 properties allow pets
Rentals with dedicated workspaces
80 properties have a dedicated workspace
Wifi availability
140 properties include access to wifi
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- Acadia National Park
- Samoset Resort
- Pemaquid Beach
- Pemaquid Point Lighthouse
- Northeast Harbour Golf Club
- Pinnacle Park
- Dragonfly Farm & Winery
- Coastal Maine Botanical Gardens
- Hermon Mountain Ski Area
- Narrow Place Beach
- Spragues Beach
- Bear Island Beach
- Sand Beach
- Gilley Beach
- Kebo Valley Golf Club
- Eaton Mountain Ski Resort
- Pebbly Beach
- The Camden Snow Bowl
- Farnsworth Art Museum
- Rockland Breakwater Light
- Pebble Beach
- Islesboro Town Beach
- Billys Shore
- Three Island Beach