
Kid-friendly vacation rentals in Waldoboro
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Top-rated kid-friendly rentals in Waldoboro
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Popular amenities for Waldoboro kid-friendly rentals
Kid-friendly house rentals

Close to the Coast, 2025 availability
We thoroughly enjoyed our stay at Samantha's place in Cushing. To say that she is "very responsive" would be an understatement. She typically responded within 10 minutes no matter what my question was. She lives a short distance away which really helped facilitate things. We had a minor issue with the Internet which required communication with the service provider, but she coordinated everything and resolved it right away. The house is totally charming - old, a bit creaky and adorable - and well maintained (no issues there). We imagined how great it would be to visit in wintertime and snuggle up to a roaring fire. They have an expansive yard with gardens great for a short evening stroll. Forest habitat behind the property was great for bird watching. The area is absolutely beautiful - quintissential coastal Maine. The Olson House (local attraction) is a few minutes drive from the house. The grounds have a walking trail along the water with fantastic views of the coast.

Spring into the season eating lobsters w/friends
Very nice place to stay big nice and clean recommended this place to everyone looking for a good place big and clean this the right place

Cheerful spacious updated 1825 Maine Farmhouse!
Second stay at the farm house. Two weeks this time. We just love it here. Plenty of space yet cozy, everything you need, lovely outdoors space. We enjooed watching the chickens, dicks and horse next door. I wish we could stay for months. Thank you, Amy and family!

Charming, Family-Friendly Historical In Town Home
This was the perfect rental for our family of 4 for the thanksgiving holiday. The home had everything we needed and wanted, great location within walking distance of so many great places in Rockland, and was clean and comfortable. Alicia went out of her way to provide recommendations for our stay! This is probably the best Airbnb we’ve stayed at and the most helpful host we’ve encountered. Highly recommend and thank you to Alicia and family for making our week so enjoyable while spending time with our kids on their college break.

Riverside
We had an amazing time over valentines day weekend. There was a snow storm and Kent snow blowed around our vehicle to make sure we could get out. The house is very comfortable and peaceful, amazing view of the river and just off the road enough to not be bothered by passing traffic. Definitely recommend!!!!

Waterfront Farmhouse with Modern Flair!
The home was very welcoming and accommodating for our family of 5. The views were spectacular at sunrise, sunset and during the snowstorm. Bald Eagles and hawks would land in the trees right in front of the house. Also, there was a skating pond down the street my family love to visit almost each evening. There was an alarm going off as soon as we arrived, Debbi was incredibly fast responding and sending someone to check it out clear it up. On the plus someone came and plowed the driveway after the snowstorm it was great. She left a basket of local food and my family ate it up. We are so thankful for our relaxing week and would love to return.

Classic Maine, Modern Comfort
We had a wonderful stay at this Maine house--Barb, the property manager was incredibly responsive, helped with a heating issue while we were there and had the repairs done same day--The house was well equipped with everything you need for a family getaway at the beach! puzzles and games galore, kitchen was fully stocked with everything needed for family meals (including lobster cooking essentials--bibs, crackers, steam pots) Great little fire pit out front which we enjoyed, and fenced in back yard area so pets or kids can be safely contained :) Linens, towels, all clean and provided--truly a wonderful home away from home, perfect for our family trip to the beach!

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!
Kid-friendly apartment rentals

Sophisticated Charm at an unbeatable price!
The apartment was just as described. Very bright, clean, and spacious. It was fully stocked with just about everything we needed during our stay. We had zero issues. The only drawback was the tiny tv in the living room. It was super small and there is plenty of room for something bigger. There were 4 of us and we really enjoyed our time at Susan’s place.

Enjoy private outdoor deck and downtown location!
I enjoyed my stay at this location. It was quiet, clean, and as described. I would stay here again if I come to Portland again. I would recommend this stay to others.

Cheerful 2 Bedroom 2 Bath Garden Apt with Laundry
Margaret’s place is very homey with all the necessities for a family gathering. The neighborhood is beautiful and close to beautiful trails

Ocean Way East End - 2
Super walkable and great for a weekend stay!

Sunny apartment overlooks Main St.
This spacious place was perfect for a getaway! So close to restaurants , shops and Belfast Harbor walk, yet so quiet at night.

Bright, Fun & Spacious Apartment on Back Cove
Ian's place was great for a girls trip ti Portland. He was a great communicator if I had any questions or cleaning instructions. Will definitely stay again for any future trips to Portland.

Bright and cozy Munjoy Hill neighborhood apartment
Sadie and Laughlin are the best Airbnb hosts we have come across. We could not have asked for a better place to stay. The apartment is very clean, has lovely furnishings, is nicely decorated and had everything we needed for a very comfortable 3 and a half day stay in Portland. Both bedrooms are a good size and have incredibly comfortable beds. When we needed help with something, our hosts came around fast to help us. If we are ever back in Portland, we shall gladly book again with them. I would highly recommend this apartment!

BEST location! HUGE 1 bedroom downtown Portland
This is a simple, beautiful, unpretentious spot. It is completely unlike a hotel room. it didn't have TV, and that was one of the nicest things about it. It is bright and relaxing to be in. It is very well situated as advertised. We would certainly stay there again!
Kid-friendly condo rentals

"Cornelia" Penthouse Waterfront Suite
What a Beautiful place! Plenty of space, clean, and super comfortable. We were amazed at the stunning views of Casco Bay! Even on a rainy day we enjoyed watching the ferries come and go. We also enjoyed being so close to great restaurants and shopping. The parking pass was very much appreciated, once we parked we never had to use the car at all. It was hard to leave this gorgeous Condo, and hope we can make it back again soon. Thank You!

Old Port on foot
Thus was a great location for our stay in Portland. Easy to get around and plenty to see and do nearby. i will definitely stay here again when I'm in the area.

⭐️✨⭐️ West End Old Port CLEAN, cozy, convenient
The apartment was exactly as described, which is seeming to be less and less popular these days. Jessica was extremely responsive to any questions or concerns. Excellent host. The place was clean, accommodating and well maintained. Walking distance to everything you need without being on top of the chaos that can be expected in downtown Portland during peak season. Highly recommend and will be coming back again.

East Bayside/ Munjoy - Charming Downtown Escape
Our group of 5 had a great experience staying here. The place was exactly as described. We had plenty of room, the location was great, and the off-street parking came in handy. Everyone raved about the water pressure in the shower, which was needed after a few long days. We would definitely stay here again. Check in was easy, and while we had no issues, I'm confident they would have been addressed quickly if needed.

First Floor Portland Condo 3 Bed 2 Bath + Parking
We loved our stay at Allyson's place, she was very helpful! Loved visiting Portland❤️!

Renovated Exchange St. Loft w/Free Parking
I’ve been to a few AirBNBs and this by far was a favorite. He had a lot of extra TP, paper towels, bath towels, dish towels, coffee and tea, pillows, blankets and cleaning supplies for both bathroom and kitchen! We’ve been to this area before and it’s so nice. And this apartment is in an amazing area. Tons of shops and restaurants. We didn’t have to drive for the weekend. We were there for a concert at cross insurance arena, and that was only a few minutes walk from the apartment. I will be renting this place out again, thank you for an enjoyable stay.

River Escape - Studio Apt. with River Access
She made cookies the moment we checked in and delivered them to us with warm milk. Wonderful host with great knowledge of the beautiful Pemaquid region

Rustic Willard Beach condo ten mins from Old Port!
What a wonderful place in a lovely neighborhood. The condo exceeded our expectations—it was even more beautiful in person. We had a comfortable, happy stay with our small children. Scratch Bakery and an ice cream parlor are right across the street! And the book collection was great. Highly recommend!
Quick stats about vacation rentals that are kid-friendly in Waldoboro
Total rentals
20 properties
Nightly prices starting at
ﺩ.ﺇ294 before taxes and fees
Total number of reviews
790 reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Wifi availability
10 properties include access to wifi
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- Fox Ridge Golf Club
- Brunswick Golf Club
- Popham Beach State Park
- Belgrade Lakes Golf Club
- Samoset Resort
- Pemaquid Beach
- Coastal Maine Botanical Gardens
- Wolfe's Neck Woods State Park
- Pemaquid Point Lighthouse
- Narrow Place Beach
- Sand Beach
- Spragues Beach
- Pinnacle Park
- Falmouth Country Club
- East End Beach
- Bradbury Mountain State Park
- Andrews Beach
- Martindale Country Club
- Lost Valley Ski Area
- Rockland Breakwater Light
- Hunnewell Beach
- Head Beach
- The Camden Snow Bowl
- Farnsworth Art Museum