Holiday rentals with outdoor seating in Kendall County

Romantic Retreat | Hot Tub, Sauna + Outdoor Shower

One of the most loved romantic cabins on Airbnb, designed for couples who want to slow down, reconnect, and experience something different. Soak under the stars in your private hot tub, sip wine by the fire pit, and wake to deer just outside your window. This peaceful Hill Country retreat blends luxury, nature, and intentional design for an unforgettable stay. ✨ Elevate your stay with curated add-ons like our Sip + Soak experience, stargazing kit, or celebration setups, available after booking.

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!

The Sunday House

Welcome to the Sunday House! Our tiny home was built by hand using reclaimed materials with your rest & relaxation in mind. This rustic romantic getaway is equipped with many amenities including a queen-sized memory foam mattress, kitchenette, full size bathroom with a shower and a wood burning stove to keep you cozy. Enjoy a complementary cup of coffee in our courtyard garden or snuggle up inside for a movie. NO CLEANING FEES 2022 Permit #2200146 Photo Credit: Aubree Lorraine Photography

Hill Country Tower

HILL COUNTRY TOWER WITH BEAUTIFUL HILL COUNTRY VIEWS This is the perfect retreat spot for anyone wanting to trade the noise of the city for a peaceful weekend filled with Hill Country views and stars you can actually see at night. The 3 story fully-outfitted tower, designed by a prestigious local architect is topped off by a deck that overlooks over 100 acres of pristine, undeveloped Hill Country property. 5 minute drive to Downtown Boerne. Updated new king size bed with luxurious mattress.

Buffalo Haus - Downtown charm 2-bedroom bungalow

A charming home on a quiet street only six blocks from Main Street's shopping and restaurants. You can rest comfortably in a king or queen size bed and wake to enjoy the stocked coffee bar. If this is a working vacation, you will love the workspace and high speed wifi. While we're minutes away from River Road and its many dining options, you may decide to stay in and use the full kitchen. Either way you'll love relaxing on the large patio under the party lights. Dog friendly home.

Cloud Dome W/ Private Hot Tub and Outdoor Shower!

Here at our Cloud Dome you'll be away from the hustle and bustle in a stunning hill-county Geodome! Take advantage of our outdoor spaces where you can enjoy a drink in the hammock bed, soak in the hot tub or indulge in your very own outdoor shower. Nestled in the trees on the edge of a small bluff your space has been carefully crafted to take full advantage of the surrounding nature all the while being in comfort and style! This luxury glamping experience is the perfect escape.

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.

Red Barn Retreat•Feed Deer Daily•8 min to Boerne

Boutique barn stay on 9 peaceful acres • Just 7 min from downtown Boerne • King suite + cozy living area w/ sofa sleeper • Full kitchen for easy meals • Outdoor games & wide open space • Wildlife under beautiful oak trees • Feed the deer with deer corn provided • Texas-themed charm with luxury touches • Brand-new mural wall by renowned artists—perfect photo spot • Relax under starry skies & explore Boerne’s Hill Country magic NO SMOKING OR VAPING (tobacco or marijuana)

Masters Lake Cabin

Come enjoy a relaxing stay at the Masters Lake Cabin in the Texas Hill Country minutes from Boerne. This beautifully restored cabin sits on Masters Lake. The property is comprised of 257 acres and features two lakes. The lakes are both stocked with bass for catch and release fishing. If you like to hike, you will find plenty of space for exploring. There is abundant wildlife to enjoy, including: whitetail and axis deer, bison, turkey, ducks and a variety of birds.

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.

Historic Hideaway.

1846 Secluded, Restored Cabin on 40 acres with Modern Finishes Take life easy at this historic cabin uniquely restored for comfort and rest. Cabin is 1/4 mile from quiet county road and has expansive ranch behind it. Quiet country living at its best. When ready for adventure, we are centrally located being forty minutes from Gruene, Fredericksburg, Marble Falls, and San Antonio! Put -in for the Upper Guadalupe is only 10 minutes away.

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.