Holiday rentals 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.

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.

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.

The Treehouse at Hill Country Nature Retreat

Explore an expansive viewpoint of the Texas Hill Country. This handbuilt, one-of-a-kind treehouse is nestled on 37 forested acres. With its unique design and stylish interiors, half mile hiking trail, hammocks, and screened in porch, the treehouse invites you unwind, rest, and recharge in nature. You won’t be surrounded by other Airbnbs here. Book a night or two and enjoy some peace. (The covered outside staircase takes you from the downstairs kitchen/bathroom to the 2nd floor bedroom.)

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.

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.

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.

Ranch Retreat, Romantic, Views, Wineries, Wildlife

Experience a tranquil, "back to nature getaway"! Spectacular views & lots of wildlife! Romantic, secluded in a nicely decorated house with everything you need! Enjoy local wineries or view whitetail deer, armadillos, fox, wild pigs, & South TX rare birds on the property! Most guests comment on the quietness and stars in the sky! Hike our acreage, visit the wineries, nearby day trips or just RELAX!