
Family-friendly holiday rentals in Westport Island
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Top-rated family-friendly rentals in Westport Island
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.
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Popular amenities for Westport Island family-friendly rentals
Family-friendly home rentals with a hot tub

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

Falmouth 3br near Town landing
David and Valle’s house is welcoming, and it was just right for our family get-together. The kitchen is very well set up for cooking, and the counter is both beautiful and a great place for gathering and conversation. There are many lovely touches in the house. We appreciated the yard and gardens, and our dog loved the walking trail. The location is peaceful but just a few minutes from Portland. David communicated well and offered helpful ideas for our visit.

Brownie- Comfy Modern Ranch Home w/Hot Tub
We love staying at the Brownie. It’s a great home for any active family that appreciates a quiet surrounding. Great home and so close to SR. It can’t be beat.

Luxury 6 bedroom Beach House 50 ft from beach
The house was beautiful and worked perfectly for our group! Check in was very easy, and the house was spotless when we arrived. My favorite part it was the yard - perfect for a big barbecue with a large group.

Private studio loft, decks and hot tub
I was happy to return to stay at Deb's, this time around in the studio loft. It was very spacious and comfortable and included anything that you might want or need. It was a perfect spot for me to rest while watching ski races at Black Mountain for the weekend. Thanks for being a wonderful host once again, Deb!

Cozy hot tub haven
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.

Nashport on the Penobscot
great stay for a relaxing weekend trip. perfect house for chilling but still drivable to Acadia. well stocked on the essentials, linens, and stunning views! host very responsive as well.

Raven's Crossing - Retreat Cottage
What an awesome place to stay! Lori was incredibly gracious and accommodating with out late arrival. The cabin towards the back of the property was so cozy. Fantastic stay and would definitely recommend!
Family- and pet-friendly home rentals

Freeport Village Sunny Studio
What stood out the most to me was how responsive Jennifer was, even before booking. It just showed how much she cares about her rental. Her and her family were very accommodating, the rental was clean and had everything we needed, and the location was perfect for a trip to Freeport! Would highly recommend! 😊

Rustic Family Cabin on China Lake
We come every year. It’s a great quiet place.

1000 sq. ft. 1BR+ Apt Close to Town & Nature
A beautiful and cozy space with lovely natural light and generous room to spread out. The full kitchen is equipped like a real home, with everything from basic pots and pans to whisks and even nut crackers! A great place for cooking full meals. A nice quiet location, even with its relative proximity to a regularly-traveled road. I'm sensitive to noise and was never bothered by sounds of traffic. Pettengill Farm is only a few minutes up the road, a beautiful place to walk for both dogs and humans and really easy to access multiple times a day. Mandana was always very responsive to communication, and when there was a glitch with Airbnb's fee calculation she was extremely helpful and approachable and took care of it immediately.

Peaceful Getaway at The Ledges
Our stay at Margaret's home was very relaxing and comfortable. Pristine bathroom, kitchen and bedding. The lake view was so much more than we anticipated. It was serene, peaceful, and breathtaking. She went out of her way to answer questions for us about the area, and we left feeling like we just gained a new friend. Jeff and Donna

Classic Maine, Modern Comfort
The perfect house! Beautiful and just like the photos. The location is perfect and just a short walkable distance to the beach. The home was roomy, clean, and had great amenities.

True Maine Artist Cottage with Outdoor Shower
Super cute cottage! I really enjoyed a few peaceful days there on my own, it was exactly what I was looking for. It's very charming and has everything you need. Like others have mentioned, you can definitely hear the road noise so it doesn't feel totally secluded but that didn't detract from my stay. Emily was a great host, provided lots of helpful information, and very quick to respond.

Superb Location w/EV Hk up & Walk to town & ocean
My husband and I stayed here with our dogs and loved it! The cottage was quaint and lovely …. And the location is perfect! Amanda was so kind and responsive! We will definitely be back when in Camden again 🌸🌲🌊

Maine Paradise at North Pond-Paddle, Fish, Swim
My family enjoyed an amazing stay at Heather‘s place over the Memorial Day weekend. Plenty of kayaking and paddle boarding, nightly fires and grilling! The beds were very comfortable and the kitchen had everything we needed for cooking meals. The shower has great water pressure! We visited several local family hikes and would not hesitate to stay again.
Family-friendly home rentals with a pool

Slopeside Sunday River Condo Brookside 2A210
Great place to stay with an awesome view of white heat!

Two-Bedroom Condo on the Wells/Ogunquit town-line
Christopher was a helpful host and his place was perfect! Clean, fully stocked, great location. It was close to lots of beaches and restaurants and the pool was great for the little ones

Beach Dreaming
A nice private cottage in a quiet community that was super handy for us to stay until we secured our house in New England. Everything is in place for comfortable living. We lived there for a month long and the hosts were always responsible.

Charming Farmhouse: POOL | Game Room | Hot Tub
The home was beautiful and exactly as pictured. We especially loved the hot tub and the outdoor fire pit, such great touches for a relaxing stay. The space had everything we needed, and we felt right at home. We’d absolutely stay again in the future if welcomed back!

Riverfront Luxury in the woods, Million $ Views.
Jon’s cabin is a beautiful place to get away from it all. Very comfortable and well designed. We had everything we needed to cook and hole up for a few days. If you decide to drive to the lake, I would recommend 4WD. We had a truck but were not aware of how soft the ground was and ended up needing to be towed out. Still highly recommend! Enjoy your stay!

The Hill's on Buttonwood
Home is very expansive with room for multiple families to reside together. Lots of games and activities for all ages. Amazing location within minutes to airport and short drive to downtown

the lake house
We had a lovely time at the cabin. Close to skiing yet peaceful and relaxing. We thoroughly enjoyed our stay ! Thank you!

Large private area, close to Rockland
We found the home clean and welcoming. There was plenty of room for all of us and we enjoyed the back deck very much. The kitchen was well equipped and although we did not do any cooking, if we had, everything was there for us. We really liked how private the home was. Had the weather been warmer we definitely would have checked out the pool. It is also very close to Thomaston, Rockland and Owls Head. So much to do in this area. We would recommend this home to anyone who wants a quiet retreat in Maine that is close to the coast.
Quick stats about holiday rentals that are family-friendly in Westport Island
Total rentals
50 properties
Nightly prices starting at
₹9,519 before taxes and fees
Total number of reviews
1.1K reviews
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
50 properties include access to wifi
Destinations to explore
- China Holiday rentals
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- Pet-friendly rentals Westport Island
- House rentals Westport Island
- Rentals with a firepit Westport Island
- Rentals with outdoor seating Westport Island
- Rentals with a patio Westport Island
- Rentals with a washing machine and dryer Westport Island
- Rentals with a fireplace Westport Island
- Waterfront rentals Westport Island
- Family-friendly rentals Westport Island
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- Sebago Lake
- Scarborough Beach
- Popham Beach State Park
- Surfside Beach
- Samoset Resort
- Pemaquid Beach
- Fox Ridge Golf Club
- Coastal Maine Botanical Gardens
- Cliff House Beach
- East End Beach
- Brunswick Golf Club
- Belgrade Lakes Golf Club
- Palace Playland
- Pemaquid Point Lighthouse
- Ferry Beach
- Funtown Splashtown USA
- Dunegrass Golf Club
- Wolfe's Neck Woods State Park
- Freddy Beach
- Crescent Beach State Park
- Portland Museum of Art
- Maine Maritime Museum
- Prouts Neck Country Club
- Bradbury Mountain State Park