Family-friendly holiday rentals in Kendall County

Dog Trot Guest Suites on the RW Ranch

Welcome to the hilltop on our 135 acre ranch. We are located in the heart of the Texas Hill Country with close proximity to everything! Our Dog Trot Guest Suites consists of 2 suites each with a queen bed, an additional sleeping area (daybed or trunnel) and private bath. Our 180 deg views are spectacular and the stars at night are big and bright! We are a short distance from Old Tunnel State Park, James Kiehl River Park, Sister Creek Winery, foodie restaurants and caves. Hope to see you soon!

Enjoy the Hill Country in Convenient Casa Paniolo

Amazing home base to explore San Antonio and Hill Country. One mile from Boerne's Main Street with great restaurants, breweries, & shopping. Tons of outdoor activities nearby. Easy drive to wineries, distilleries, Six Flags Fiesta TX, and airport. Dedicated carport and extra parking spaces right in front. Private patio and yard. Two full work stations. Perfect for remote workers. Full kitchen and stocked coffee/tea bar. Two master beds w/ private baths + sleeping loft & 1/2 bath in living room.

Treehouse Glamping at Pecan Haven! Private HotTub!

Suspended 10 feet in the air, Pecan Haven is luxury glamping at its best, our tent includes a king size bed, A/C, indoor bathroom with walk-in shower, private hot tub, coffee, wifi, and more. Relax outdoors, take a nap in your hammock chairs, indulge in a soak in your private hot tub, or avail yourself of the private outdoor shower. This Treehouse also has a smart TV for your Netflix and movie binge nights. This treehouse has everything you'll need for a fun, relaxing stay in the hill country.

Oaks Ranch - Home near Guadalupe River St. Park

Beautiful and comfortable, a unique get away in the heart of Texas hill country, one mile south of Guadalupe St Park and next to beautiful Park-31 wedding venue. We are minutes from small towns and a big city that offers unique and multicultural experiences, shopping, dining, and recreation. Guadalupe River Park is easily accessible and offers water recreation, camping, and day hikes. As a working ranch you will fall in love with the animals who live there and enjoy their close interactions.

Private|Quiet|Hilltop|57Acres|Wildlife|HotTub|Pool

Welcome to Grandview Wildlife Ranch - A scenic hilltop hideaway on 57 private acres. GWR is your peaceful getaway in the Texas Hill Country. This private ranch setting is ideal for couples looking to unwind with expansive views, charming rustic interior and thoughtful amenities. The ranch is quiet and cozy and offers a retreat like no other. Soak in our luxurious hot tub, cool off in the cowboy pool, dark sky area for star gazing, hiking and explore the property in our Kawasaki Mule rental.

Breathtaking Views 2BR, Hot Tub, Private, Firepit,

NEW HOT TUB installed! Escape to your peaceful 2BR/2BA private Ranchette in Kendalia, TX! 1.5 hours from Austin, this luxurious retreat offers an incredible experience with rolling hills, you'll be mesmerized by the epic panoramic views that stretch as far as the eye can see! Indulge in the ultimate relaxation with your relaxing hot-tub and firepit in the cold months, with breath-taking views while you soak up the Texas sun. At 29 acres, this cabin offers complete privacy and tranquility

The Texas River Property (Now w/Starlink)

8+ acres of private, water front property with a beautiful home that is all yours for the duration of your rental. This property boasts river access immediately on property, just walk right on down to the Guadalupe and set your chairs up to enjoy a day in the cool flowing waters of one of Texas's finest rivers. The acreage offers open land to run, play and explore all around. Upgraded internet through Starlink gives excellent wifi. Check out the photos and message us with any questions.

Feed Deer Daily |Peaceful Hill Country Cozy Cabin

Nestled under towering oaks just 7 minutes from Boerne, the Cozy Oak Cottage offers a peaceful Hill Country escape where nature and comfort meet. Sip coffee as deer wander by, spot our friendly free-range chickens exploring the grounds, and enjoy the beautiful wild birds that visit the birdbath. A stylish, cozy interior, fast WiFi, and warm, thoughtful touches create a stay where guests feel genuinely cared for from the moment they arrive. Tap ❤️ and book your serene retreat today.

Hill Country Cabin in the woods

Our cozy one room cabin is tucked away in a peaceful wooded area, accompanied by the sounds of a running creek just out front. This spot is a great place to relax and unplug from the busyness of life. Enjoy a stroll or hike alongside the creek, plop some chairs in the water and take in the sounds of nature. Kids enjoy exploring, wildlife and roasting marshmallows while snuggling up around a campfire. The experience is much like camping, not to be compared with a hotel.

The Riverwood - A Hill Country retreat!

The Riverwood cabin was built by the property owner (Oso), a direct descendant of Dr. Herff, an early settler to Boerne in the 1850's. The rustic, craftsman-built cabin sits on an 85 acre historic ranch and wildlife preserve, located just 2 miles from downtown Boerne Square. The cabin is a bit quirky, and definitely an experience, yet has all the comforts you will need for a relaxing stay with friends or family! Please read house rules before booking.

Hill Country Manor Estate | Heated Pool • Horses

Escape to a serene retreat on 8 picturesque acres, where peace and tranquility meet convenience. Despite the secluded feel, you’ll find popular spots like H-E-B, IHOP, Starbucks, Burger King, and Taco Bell just a 2-minute drive away. Enjoy easy access to local attractions, with the Guadalupe River just 15 minutes away, and New Braunfels and Canyon Lake only 25 minutes from the property. Plus, the San Antonio Airport is just a short 25-minute drive

Lucky Stars Tiny (Luxury) House - Boerne TX

Lucky Stars sits on 7 beautiful, native acres, tons of wildlife, just ten minutes from Boerne, with stargazing at its best! Upscale on a small-scale, 200 sf with fully-equipped kitchen, on-level Queen master bed, Smart TV, WiFi, full-size bathroom, outdoor living/shower on the deck, and more. Loft space has handmade linen/wool mattress (2 Twins or King). Built on DIY’s Tiny Luxury 2017-Season 3 Ep.3. Long-termers and short-termers always welcome.