Kid-friendly holiday rentals in Highland County

Find and book unique family-friendly rentals on Airbnb

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Popular amenities for Highland County family-friendly rentals

Kid-friendly house rentals

Top guest favourite
Home in Leesburg
5 out of 5 average rating, 14 reviews

Country Get-A-Way

KonnerRating, 5 stars16 months ago
Great place, Mary is the best host we’ve dealt with made our stay enjoyable.
Guest favourite
Home in Bainbridge
4.9 out of 5 average rating, 62 reviews

The Cottage on Cave

StephanieRating, 5 stars2 days ago
Second time we have stayed for a week with a group of 7. Plenty of room, really enjoy the screened in front porch. Also like the ability to star gaze on the back porch. Super close to Paint Creek and Rocky Fork, but very private and secluded. Just as beautiful as the pictures.
Home in Hillsboro
4.95 out of 5 average rating, 19 reviews

Ravenwood Lodge at the Highlands Nature Sanctuary

StephenRating, 5 stars22 months ago
Host was very proactive, preserve was beautiful. Great trail down the bluff along the stream, made for a cool break on a hot day, and very private feeling. Thanks!
Top guest favourite
Home in Hillsboro
5 out of 5 average rating, 28 reviews

~Lakeside Oasis~ Waterfront w/HotTub, Sauna & Dock

МагерRating, 5 stars3 months ago
We liked everything very much, the bathhouse is good, we will definitely come back again, thank you.
Top guest favourite
Home in Leesburg
4.98 out of 5 average rating, 43 reviews

The {bigger}Pond View House

ChloeRating, 5 stars1 week ago
Carole’s place is serene and spacious. The double floor plan really helped the group I hosted feel comfortable and enough room for everyone. Very very clean. Caring hosts. Quiet. Will definitely book again for my next retreat
Home in Hillsboro
4.47 out of 5 average rating, 17 reviews

Hillsboro Hideaway w/ Private Hot Tub & Bunkhouse!

JoshRating, 5 stars8 months ago
My team and I had a great stay! We had a great time together, the space was great, and we got some nice local eats, too. Super satisfied.
Top guest favourite
Home in Hillsboro
5 out of 5 average rating, 28 reviews

Hillsboro Country Retreat

WynetteRating, 5 stars1 week ago
Nice quaint house with beautiful landscaping. Great outdoor seating and entertaining area to accomodate several guests. Laura ensured we had everything we needed and even gave us welcome baskets upon arrival which was a nice touch. Would definitely book again.
Home in Hillsboro
4.63 out of 5 average rating, 32 reviews

ROCKY FORK LAKE HOUSE! 5 MIN WALK TO THE LAKE!

LeviRating, 5 stars3 months ago
Great place to stay with family. Host was amazing. House was comfortable. Would definitely book again if back in the area.

Family-friendly apartment rentals

Top guest favourite
Flat in Augusta
4.97 out of 5 average rating, 101 reviews

Top Shelf Loft on Main St

ClintRating, 5 starstoday
Augusta is a beautiful town and was outstanding! Had a blast at the Augusta Pub underneath the loft and an amazing dinner at the Beehive!
Superhost
Flat in Augusta
4.85 out of 5 average rating, 33 reviews

Charming Retreat - Relaxing King Bed

HaleyRating, 5 stars2 weeks ago
Rodney was super helpful and accommodating and helpful both before our stay and during. The room was neat, clean, and spacious. Perfect for 2 people. It had everything we needed ready to go (including complementary ear plugs for the train!). We love Augusta and can’t wait to come back again soon! Thank you again Rodney for the great stay!
Guest favourite
Flat in Centerville
4.9 out of 5 average rating, 286 reviews

Apt 1: Octopus Garden in Uptown Centerville

LarryRating, 5 stars6 days ago
Another great stay in Centerville. This rental is everything we are needing, for a quick trip to see family. See you next time!
Guest favourite
Flat in Wilmington
4.84 out of 5 average rating, 354 reviews

Nana's Nest in historic, quaint small town.

AlexandriaRating, 5 stars1 month ago
The pictures do not do this property justice. It is so charming with tons of character! It includes upgraded amenities. Location is great as well; close enough to the fun, but has private area as well. Definitely recommend and we look forward to staying again!
Guest favourite
Flat in Waverly
5 out of 5 average rating, 6 reviews

The Willow North

TamiRating, 5 stars2 weeks ago
Another great stay! As a travel nurse I always look for accommodations that have everything I need to cook meals and do laundry. This Airbnb checks all the boxes!
Top guest favourite
Flat in Lebanon
4.98 out of 5 average rating, 145 reviews

Beach House

JamesRating, 5 starstoday
April's place was great, and exactly as described. I got very clear instructions for check-in ahead of time, and everything was smooth and easy. The place was clean and tidy, had everything you could need, and was in walking distance of some nice places to eat. Overall, it was a great find.
Superhost
Flat in Chillicothe
4.88 out of 5 average rating, 101 reviews

The Foxglove

PatrickRating, 5 stars4 weeks ago
Retire, traveled for 25 years, the bed was one of the top 5, I have enjoyed. For a century home the room was spotless, the original wood floors were beautiful. The neighbor hood is a series of century home on a quiet street. Walked to the local restaurants everything is 10 minutes close. We’re enjoyable visit.
Guest favourite
Flat in Wilmington
4.91 out of 5 average rating, 104 reviews

Beautiful studio 1 bedroom apartment on 3rd floor.

LaurenRating, 5 starstoday
One of my favorite places to stay when in town to show at WEC. Had a small snafu with checking in but Jessie was extremely responsive and helpful. looking forward to staying again in a couple of weeks!

Family-friendly apartment rentals

Top guest favourite
Apartment in Wilmington
4.98 out of 5 average rating, 81 reviews

The Beach House- 2.8 Miles to WEC

CindyRating, 5 stars1 month ago
Loved the beach house. Came here to attend a horse show at world equestrian center. The location was so convenient, but the house itself was so tastefully and thoughtfully decorated, it was a relaxing pleasure to enjoy. The home is wonderfully stocked with everything you might need, recently updated. Very clean and very, very comfy. Would definitely stay here again. It’s on my favorite favorites list!
Top guest favourite
Apartment in Wilmington
4.99 out of 5 average rating, 81 reviews

Easy Street-The Rustic Equestrian-2.8 miles to WEC

AndrewRating, 5 stars2 months ago
This is the second time we have rented from Heath and Trish and once again we have nothing but great things to say about them. We will continue to use them and recommend them to our friends travelling to the Wilmington area.
Top guest favourite
Apartment in Wilmington
4.99 out of 5 average rating, 76 reviews

The Tranquility - 2.8 Miles from WEC

TiffanyRating, 5 starstoday
This place was the perfect little studio For my daughter and I to stay for her horse show. Took 4 minutes to get to the world equestrian center and only 3 minutes to a gas station and 10 minutes to Kroger or Walmart. Close to everything needed! Had lots of amenities especially a great amount of towels in the bathroom. Cute patio to leave our cooler. Friendly hosts!
Guest favourite
Apartment in Clarksville
4.91 out of 5 average rating, 34 reviews

Lovely village apartment close to World Equestrian

DeniseRating, 5 stars2 months ago
We could truly feel the love and care in every detail of the house. Everything was perfectly maintained, with clear instructions that made our stay easy and comfortable. We felt completely at home. It was a wonderful experience, and we would definitely love to come back!
Top guest favourite
Apartment in Clarksville
4.96 out of 5 average rating, 74 reviews

Rural apartment close to World Equestrian Center

RachaelRating, 5 stars1 month ago
Great place to stay, clean, bedrooms were roomy.
Top guest favourite
Apartment in Wilmington
4.99 out of 5 average rating, 86 reviews

Easy Street - The Farm House, 2.8 miles to WEC

MichaelRating, 5 stars2 months ago
Great experience overall. Everything was very clean and felt very welcoming from the moment we pulled up and entered the home. Would stay again.
Superhost
Apartment in Wilmington
New place to stay

Easy Street -The Modern Escape 2.8 miles to WEC

Destinations to explore