Holiday houses in Kendall County

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Top-rated holiday rentals in Kendall County

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite

The spacious private pool is surrounded by natural stone, with lounge chairs positioned around the perimeter. A windmill adds a rustic touch against the backdrop of rolling hills and scattered trees, creating a serene outdoor space ideal for relaxation.

Home in Boerne

250 Acre Ranch on Guadalupe River w/ Pickleball!

(Pickeball!/Hayride!) Offering our family's 250 acre private ranch for your family. Enjoy a wonderful adventure at the Poco Loco Ranch - breathtaking land, nestled in the Texas Hill Country (near Boerne) -1/4 mile exclusive access to the Guadalupe River. Included is a historic 19th century ranch house, large private pool, cabana guest house & separate kitchen and enormous game room. River access allow for amazing tubing and hiking & a NEW Pickleball Court! Free Hayride with 4 night rental!

4.91 out of 5 average rating, 43 reviews

Top Guest favourite

A spacious living area is highlighted by a gray sofa adorned with blue cushions. Two windows allow natural light to flood the room, complemented by a wooden side table and a light-colored armchair. A decorative wall clock and potted plants add subtle charm to the neutral decor.

Home in Boerne

Firefly Flats - Walk to Downtown

Welcome to Firefly Flats, Wanda, located just 2 blocks off beautiful Historic Main Street Boerne. The home is located central to shopping, restaurants and parks. This beautiful, clean, family & pet friendly home offers a great stay for couples, families & small groups alike. Perfect for weekend getaways, couples retreat, girls/guys weekend or a family vacation. Enjoy a large screen TV, Disney+, high-speed internet, RO water, fire pit, patio, hotel quality towels and linens. Small dogs welcome!

5.0 out of 5 average rating, 140 reviews

Guest favourite

A modern ranch house is presented with a welcoming facade featuring a covered entryway and large front doors. Two chairs are positioned on the porch, surrounded by landscaped gravel and natural stone. Lush trees are visible in the background under a clear blue sky.

Home in Spring Branch

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.

4.96 out of 5 average rating, 206 reviews

Top Guest favourite

A serene view of the hilltop cabin is captured at dusk, showcasing a spacious deck with seating areas and red umbrellas. The cowboy pool is visible nearby, and the cabin’s warm lights create a welcoming atmosphere against the backdrop of the natural landscape.

Home in Fredericksburg

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.

5.0 out of 5 average rating, 245 reviews

Top Guest favourite

The tree tower structure features multiple levels connected by an outdoor staircase. Glass walls provide a view of the surrounding trees, while a wooden deck with seating is visible at the entrance. A stacked log section rests beside the pathway, enhancing the natural setting.

Tower in Fredericksburg

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.

4.96 out of 5 average rating, 178 reviews

Top Guest favourite

Cabin in Boerne

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.

5.0 out of 5 average rating, 227 reviews

Top Guest favourite

Shipping container in Blanco

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.

5.0 out of 5 average rating, 118 reviews

Top Guest favourite

A serene bedroom features a spacious bed covered in a white decorative blanket, surrounded by large windows that allow natural light. The wood-paneled walls and floor create a warm atmosphere. A small wood-burning stove is positioned beside a minimalist chair.

Treehouse in Blanco

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 cold AC and heat, unique interiors, 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.)

4.99 out of 5 average rating, 192 reviews

Guest favourite

A cozy cabin is set among trees, featuring a front porch with rocking chairs. Warm lighting can be seen through large windows, and a metal roof reflects the natural outdoor surroundings. A pathway lined with rocks leads to the entrance.

Cabin in Spring Branch

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.

4.95 out of 5 average rating, 307 reviews

Top Guest favourite

Home in Bulverde

Hill Country LUX | 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

4.97 out of 5 average rating, 124 reviews

Top Guest favourite

Dome in Boerne

Glamping - Stargazing + Hot Tub • Wild KingDome

There's a moment when you step onto the deck and the Hill Country just opens up — pasture, sky, deer in the trees, cattle grazing in the distance. The Wild KingDome is a private geodesic retreat on a historic Boerne ranch. Two king beds, hot tub, 30-ft Double paned glass bay window, 15-ft ceilings. Perfect for a romantic escape, friend getaway, or small family trip. Stargazing skies at night. Downtown Boerne, 7 minutes away.

4.98 out of 5 average rating, 98 reviews

Top Guest favourite

A cozy home with a welcoming porch is surrounded by lush greenery and hills. The slanted metal roof reflects the natural landscape, while shaded seating areas invite relaxation. The property features a mix of trees and open spaces, enhancing the secluded atmosphere.

Cabin in Fredericksburg

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!

5.0 out of 5 average rating, 233 reviews