Family-friendly vacation rentals in Kendall County

Comanche House on the RW Ranch.

We’re located in the heart of the Texas Hill Country nestled atop a picturesque hill. Comanche House has 2 bedrooms, each with 2 queen beds and private baths. Our great room has views from every window and is open concept living area & kitchen. No hill country abode is complete without a front porch for enjoying the 180 degree views. We’re the perfect hub for all the beauty the Hill Country has to offer. Close to Historic downtown, shopping, foodie restaurants, wineries, state parks & caves.

Country Guesthouse in Boerne | Bluebonnet Oasis

2 bedroom/2 bath guesthouse just minutes from downtown Boerne. Large game room with pool table and movie projector 120” screen with amazing surround sound and a 65”LCD. Step out to the firepit and huge pool, shared only between the two guesthouses. New small kitchen with all new appliances. We welcome pets with a $20 pet pet feeNO PITBULLS AND ONLY 1 LARGE DOG Unsupervised pets must be crated. Just added relaxing water feature, new pool volleyball net and basketball hoop Super fast wifi

Chertecho Tree Tower

Designed to connect with the natural systems of a special place, Chertecho sits among the trees on a 5-acre rocky slope overlooking the Pedernales River Valley. An outdoor stair system connects the three levels - a covered rooftop deck; a second-floor master suite; and a ground floor kitchen space. Glass walls open to the wooded slopes of Big Hill, a ridge separating the Pedernales and Guadalupe watersheds halfway between Comfort and Fredericksburg. A place to unplug, and reconnect.

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.

Haven House - Home near Guadalupe River St Park

Beautiful and comfortable, this gorgeous getaway is in the heart of Texas hill country, one mile south of Guadalupe St Park and next to the 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 horse ranch, you will enjoy the close interactions with our animals!

New luxury container w/deck hot tub amazing views

Contain and Chill is a place to do just that "chill." You can relax by the chiminea with a glass of wine, curl up to a good book in the hammock, or hit the deck 12 feet high or 20 steps up overlooking the hill country. The deck has a two-person hot tub and sitting area to enjoy the panoramic view of the hill country and catch the most breathtaking sunsets. This view takes stargazing to a whole new level. This unique home is not just a couple's getaway; it's an experience.

Hill Country Cabin in the woods

Escape to our cozy one-room cabin nestled in a peaceful wooded setting—the perfect place to relax and unplug. Enjoy a stroll or hike to the creek, listen to nature, spot wildlife, roast marshmallows, and gather around the campfire. Kids love exploring the property. The experience is rustic, much like camping, rather than a hotel stay. ***Please note: due to drought and summer heat, the creek no longer flows directly in front of the cabin but is a short walk away.

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.

Hill Country Carriage House

We have everything you need for a romantic getaway, business travel or fun family time. We live in a wonderful neighborhood where deer and chickens roam free. We are about a 5 minute drive to/from Main Street and in the very heart of the Texas Hill Country. Southern hospitality, hiking trails, wineries, brew haus, music venues and everything the great HC offers is here. Come be our guest! Read entire site for info! We look forward to meeting you.

Secluded Hill Country Cabin | Pool + Stargazing

Cowboys & Dreamers is a secluded luxury retreat tucked into the rolling hills of Kendalia — designed for slow mornings, dark skies, and unforgettable Texas Hill Country sunsets. Whether you’re planning a romantic getaway, wellness retreat, anniversary trip, weekend escape, or simply searching for a peaceful luxury cabin in the Texas Hill Country, Cowboys & Dreamers offers a stay that feels restorative, grounding, private, and unforgettable.

Luxe Yurt, heater, w/ hot tub, sunset&hill country

Escape the hustle and melt your cares away in the hot tub at this unique luxury yurt in Boerne! A nature lover’s retreat, butterflies abound and two mini splits keep you perfectly cool or cozy. Just 2 miles to downtown Boerne, 14 to San Antonio, and 36 to Fredericksburg—it’s the perfect spot to reconnect with nature. Enjoy fresh eggs from our hens, homemade bread, and our signature goat milk soap during your stay.

The Cabin at Hill Country Nature Retreat

Explore a stylishly unique cabin nestled in the heart of the Texas Hill Country. Our handbuilt, secluded cabin has wall-to-wall windows, with expansive views and a truly immersive experience in nature. Enjoy both modern comforts and eco friendly amenities, including a walking trail to the Ancient Oak tree, a unique opportunity to visit with our chickens, and a rooftop deck with miles of hill country views.