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Family-friendly holiday rentals in Islesboro

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Islesboro family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favourite
Cabin in Appleton
4.89 out of 5 average rating, 307 reviews

Raven's Crossing - Kate's Cottage

KendraRating, 5 stars3 weeks ago
A beautiful rustic cabin in an amazing spot. Lori is a great host and is always near in her farmhouse to communicate and get you what you need. Appleton is not far from Camden / Rockland but has that rustic getaway feel. The option of adding a wonderful soak in the hot tub, wood fired sauna, massage and breakfast are available as well. I’ll be back next year! Thank you for everything, Lori!
Farm stay in Searsport
4.91 out of 5 average rating, 112 reviews

Latham Blueberry Farm for up to 6 guests.

AshleyRating, 5 stars10 months ago
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.
Top Guest favourite
Home in Woolwich
5 out of 5 average rating, 43 reviews

Amazing view, eagles, hot tub, 1 mi walk from Bath

GregoryRating, 5 stars3 weeks ago
Sometimes photos just don't do the real thing justice, and this is the case with this property. The property and the views are truly spectacular! The home is huge and has everything you could ever need to live for a week or more. The porch, especially the screened in portion are magnificent and the hot tub was a perfect way to finish up a great day. We had so many plans to adventure out, but found ourselves wanting to stay and enjoy the pristine yard or just sit on the porch and enjoy each others company, we didn't want or need to leave. Having coffee and watching eagles fly by over the river was truly spectacular. Judy is one of the nicest, easiest hosts we have had the pleasure to work with and truly appreciates your patronage. And Hugh's journal on all things Graywood is a lifesaver. Not only would we return again, but we look forward to it.
Top Guest favourite
Home in Holden
4.96 out of 5 average rating, 246 reviews

Central Chalet

SonjaRating, 5 stars3 weeks ago
Our 2nd stay with Dwayne and Pati, it never disappoints. Private home, beautiful surroundings.
Guest favourite
Treehouse in Georgetown
4.97 out of 5 average rating, 341 reviews

Tree Dwelling with Water Views & Cedar Hot Tub (2)

JustinRating, 5 stars3 weeks ago
Beautiful spot to stay at, we didn’t get so lucky with how weather panned out but it didn’t take away from the experience we had. Would recommend to anyone!
Guest favourite
Apartment in Topsham
4.87 out of 5 average rating, 552 reviews

Cozy hot tub haven

ColeRating, 5 stars4 days ago
Nice stay, nice host, lots of recommendations in binder for things to do. Nice hot tub. Cozy place and location. DQ right across the street.
Guest favourite
Cottage in Verona Island
4.89 out of 5 average rating, 172 reviews

Nashport on the Penobscot

AmyRating, 5 stars1 day ago
We had a very relaxing vacation. Verona Island is convenient for day trips to a number of attractions like Acadia, Camden and even Monhegan Island. Even when the weather was bad there was plenty of table space for puzzling, Bananagrams and Scrabble. The house was comfortable with views of the Penobscot River.
Guest favourite
Loft in Lincolnville
4.96 out of 5 average rating, 47 reviews

Oceanfront Loft with gorgeous water views & beach!

JenniferRating, 5 stars3 weeks ago
This place is so lovely and peaceful. We loved the water view from the loft and roaming the beach. It is a great spot.

Family- and pet-friendly home rentals

Guest favourite
Cabin in Dresden
4.95 out of 5 average rating, 186 reviews

McKeen's Riverside Retreat

KathleenRating, 5 stars1 month ago
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..
Guest favourite
Cabin in China
4.89 out of 5 average rating, 177 reviews

Rustic Family Cabin on China Lake

JamesRating, 5 stars2 weeks ago
We come every year. It’s a great quiet place.
Guest favourite
Home in Surry
4.94 out of 5 average rating, 155 reviews

Gran Den Lakefront Home Near Acadia

SharonRating, 5 stars2 weeks ago
Great stay for our family of 5 adults and 3 toddlers! Lots to do and great proximity to Acadia/Bar Harbor. House was well supplied with clear instructions. Brady also connected with us before the stay and kept in touch for anything that came up as a concern. Thank you!
Guest favourite
Cabin in Boothbay
4.95 out of 5 average rating, 446 reviews

Simple Boothbay Log Cabin on Water

TorreyRating, 5 stars3 days ago
Elia's cabin is magical. What a beautiful and peaceful place. We had everything we needed, but be sure to bring bug spray.
Superhost
Treehouse in Hancock
4.95 out of 5 average rating, 541 reviews

Treehouse near Bar Harbor. Luxurious and private!

Emily Rating, 5 stars4 days ago
We absolutely loved our stay here at the tree house!! The shower and sauna were so relaxing. It’s was so peaceful! The hosts were so friendly and sweet. We will absolutely be saving this for future stays:)
Guest favourite
Cabin in Deer Isle
4.88 out of 5 average rating, 144 reviews

Long Cove Artist Cottage

Carmen Rating, 5 stars3 weeks ago
My husband and I spent a wonderful week at Judith’s cottage in Deer Isle. Judith, her partner Linda, and Kate (Linda's daughter) were incredibly welcoming—always kind, helpful, and full of great recommendations about the area, from hiking trails and restaurants to local shops and the island’s fascinating history. We truly enjoyed our conversations with them, and they were also very respectful of our privacy. The cottage is rustic but cozy and comfortable, with everything we needed for a relaxing stay. The Wi-Fi worked well, and the garden and views of the cove were beautiful. It’s also a great location for exploring Deer Isle, the Blue Hill Peninsula, and even Acadia National Park. We’re grateful for the hospitality and would gladly return!
Guest favourite
Campsite in Penobscot
4.98 out of 5 average rating, 122 reviews

Private Lakeside Camping in Penobscot, Maine

CourtneyRating, 5 stars2 days ago
Great spot right on the lake! Very quiet and beautiful, it felt like we were the only ones on the lake. Perfect little camp to explore the area, it had everything we needed. The warm shower was perfect and much needed after primitive camping for a few days. The camper was super cozy, too. Would gladly visit again!
Guest favourite
Home in Newcastle
4.91 out of 5 average rating, 201 reviews

Rustic Farmhouse at Oxbow Brewery

CatherineRating, 5 stars3 weeks ago
My husband and in-laws and I and our two dogs stayed for a long MDW. The weather did not cooperate but did not hinder us. Especially staying at this Airbnb on the beautiful Oxbow Brewing property. In fact the coziness of the space made a rainy day even more fun. We were visiting for the racetrack and location was excellent for privacy and also close to local attractions. Wish we had more of a group to experience the space with us, it was really special!

Family-friendly home rentals with a pool

Top Guest favourite
Apartment in Cornville
4.87 out of 5 average rating, 134 reviews

Large Home with Great View next to horse farm

WilfredoRating, 5 stars3 weeks ago
Beautiful and peaceful place! Just admiring the surroundings let the peace and tranquility set in and consume you. Highly recommend! Teresa is a wonderful host and flexible to your needs. Will definitely visit again, thank you Teresa!
Top Guest favourite
Apartment in Boothbay Harbor
5 out of 5 average rating, 32 reviews

Luxury Condo on Water's Edge in Boothbay Harbor

HollyRating, 5 stars2 months ago
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.
Superhost
Home in Stonington

Kate's House at Spruce Harbor

ShokiRating, 5 stars9 months ago
Cannot imagine a better spot to relax with our family. A lucky spot for the owners and luckier for us that they share the rental with strangers.
Superhost
Apartment in Rockland

Heart of Rockland Maine

DeborahRating, 5 stars9 months ago
Aimee was wonderful to deal with. Her place was absolutely beautiful. we definitely picked the right place. the sunrises were so awesome. Rockland was a gorgeous little town.
Condo in Rockport

Samoset Resort Oceanfront Large One Bedroom

JamesRating, 5 stars72 months ago
Great unit on the golf. Course with Ocean views out to the islands. Generally peaceful, save for the morning mowing of the golf course. Great place to base to see all of the mid-coast and the Samoset hotel amenities that are available to you are first class
Home in Harpswell
5 out of 5 average rating, 8 reviews

The Point, At The Edge Of The Ocean

KamalaRating, 5 stars9 months ago
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!
Condo in Rockport

Samoset Resort Oceanfront Condominium

ArleneRating, 5 stars84 months ago
This place is absolutely amazing. It was larger than expected. It looked smaller in the pictures. Everything in the apartment was squeaky clean and we had every single thing we needed, from pots and pans to board games. Great ocean view from the porch, the living room and from one of the bedrooms. I loved seeing the boats pass by. So peaceful! I stayed there with my elderly mom, my teenage daughter and her friend for 4 days. There was so much to do! We enjoyed both the outdoor and the indoor pool. The kids took advantage of the Health Club by playing ping pong, badminton and going to the video game room. They also spent several hours playing chess in a very nice room near the lounge area that had a gorgeous ocean view. We had dinner at the Italian restaurant in the resort and were impressed by the amazing view. Great service. We also enjoyed the long walk to the lighthouse right next to the resort, and loved going to Camden, such a charming little town, 10 minutes away. The hostess, Laurie, was very accommodating, super nice, and communicated with me frequently, making sure I had all the answers I needed. I would definitely go back there! Glad to have made such wonderful memories! We didn't want to leave!
Home in Lamoine

Close to Acadia National Park

EdmundRating, 5 stars34 months ago
Valerie's home was clean and in a quiet neighborhood peaceful stay

Quick stats about holiday rentals that are family-friendly in Islesboro

  • Total rentals

    140 properties

  • Nightly prices starting at

    $134 NZD 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

  • Wi-Fi availability

    140 properties include access to Wi-Fi

Destinations to explore