Vacation rentals in Kendall County

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Top-rated vacation rentals in Kendall County

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

Guest favorite

Home in Boerne

5 out of 5 average rating, 75 reviews

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, fire pit, outdoor patio, hotel quality towels and linens. Small dogs welcome!

Superhost
A cozy living area features wooden tongue and groove walls, accented by a decorative area rug. A comfortable sofa and chairs provide seating, complemented by a circular mirror and artwork on the wall. Large windows allow natural light to illuminate the space.

Home in Fredericksburg

4.88 out of 5 average rating, 164 reviews

Twilight Ranch - cabin w/hot tub and dog friendly!

Escape to the Texas Wine Country of Fredericksburg, TX in this charming farmhouse cottage. This ranch is situated halfway between Fredericksburg and Comfort TX and is a perfect home base as you explore the Texas Hill Country. Only a 5 min drive away, see the bats at Old Tunnels State Park and eat at the Alamo Springs Cafe (who claims the best burger in Texas). Luckenbach dance hall or many wineries and the 290 wine trail are a 20 min drive and Bankersmith restaurant is only 10min drive.

Guest favorite
A rustic wooden table displays two glasses of red wine alongside a wine bottle, set against a backdrop of rolling green hills and distant mountains. Natural elements are integrated into the table's design, enhancing the outdoor atmosphere.

Cabin in Fredericksburg

4.99 out of 5 average rating, 185 reviews

Ranch Retreat, Romantic, Views, Wineries, Wildlife

Experience a hilltop ranch w/ spectacular views and lots of wildlife! Romantic, secluded w/ great VIEWS in every direction. Perfect for a "get away from it all" experience. 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 the acreage, visit the wineries, nearby day trips or just RELAX! We've added new house on other side of ranch w/ it's own road for privacy.

Guest favorite
A cozy outdoor seating area is framed by large trees and features two black wire chairs positioned around a charming fire pit. The cabin's large glass wall allows views of the warm interior, which is softly illuminated as evening sets in.

Guest suite in Pipe Creek

4.96 out of 5 average rating, 150 reviews

Madrona Ranch Casita | Private Hot Tub | Pets OK

Perched on a hillside overlooking Red Bluff Creek, the Casita at Madrona Ranch has everything you need for a relaxing family getaway! This is one of the best waterfront cabin rentals we have at Backroads Reservations, with its amazing views of the Hill Country, quiet rural setting, and convenience to the shops and attractions of nearby Pipe Creek and Boerne. Inside and out-from the tree-lined property to the rustic beamed ceilings, this sweet little cabin has to be seen to be believed!

Guest favorite
A spacious bedroom features a plush bed with a light-colored tufted headboard and an assortment of decorative pillows. Soft bedding and a cozy throw are present, while side tables flank the bed. Natural light enters through a large window adorned with light curtains.

Home in Boerne

5 out of 5 average rating, 40 reviews

Cottage Home off Main St. Boerne-New & 5 Stars!

"The Cottage" is a luxury whole home rental 3 minutes from the heart of Downtown Boerne. A two block walk from famous Bakery Lorraine (a must go to for coffee, pastries and more). Fully stocked and intentionally prepared before your arrival, you'll find everything you need in this home. With high end finishes throughout the home, comfortable beds, fast wifi, a spacious fenced in yard with a fire pit, and a welcome gift with your arrival, this home will be your favorite getaway spot.

Guest favorite
A view of a tastefully decorated bedroom is captured through a doorway. The rustic charm of wooden walls is complemented by soft lighting and a ceiling fan. A mirror frames the scene, reflecting a cozy atmosphere and inviting rest.

Home in Comfort

4.98 out of 5 average rating, 175 reviews

High Street Guesthouse - Comfort Historic District

Located in Comfort's Historic District, High Street Guesthouse is steps away from local events, unique shops, restaurants and wineries. Family owned since it was built in the early 1900's, High Street Guesthouse was fully renovated to include modern amenities while maintaining the original history and charm. Entire Guesthouse available for 1 to 8 guests. Enjoy your time in "Comfort" at the quintessential High Street Guesthouse. WiFi recently installed

Superhost
A stone house nestled among trees is illuminated by the warm glow of sunset. The structure features a sloped roof and multiple windows, allowing natural light to enter. The entrance is framed by some shrubs, providing an inviting appearance amidst the natural surroundings.

Home in Boerne

4.86 out of 5 average rating, 63 reviews

The Guadalupe River Retreat | Deer | Birds | Views

Imagine a private riverside resort, a kid-friendly and pet-friendly hideaway loaded with luxurious amenities, and tons of fun and relaxing things to do. All this and more awaits you at the Guadalupe River Retreat, one of the best Hill Country vacation destinations, tucked away in the gorgeous mountainous terrain just outside Boerne! It's perfect for nature lovers and travelers alike with its rural setting, but with the charming city of Boerne close by.

Superhost
A covered outdoor space is showcased alongside a relaxing pool, featuring two sun loungers and a table with chairs. The area is bordered by a wooden fence, and trees provide a backdrop, enhancing the inviting atmosphere for outdoor enjoyment.

Home in Boerne

4.83 out of 5 average rating, 30 reviews

The Not So Ugly Duckling

Your family will be close to everything when you stay at this centrally-located place. We have a Local favorite restaurant on the same street The Dodging Duck.. across the parking lot is a fun local bar Salvador Dobbs with signature cocktails and a fun patio! Don’t miss Thursday night karaoke at Dobbs!! Walking distance to Main-street with tons of fun breweries and restaurants! Perfect location!!

Guest favorite
A charming single-story retreat is set against a vibrant sunset, showcasing large windows that illuminate the home. The inviting front porch features ample seating, while the surrounding natural landscape features mature trees and sparse grasses, creating a tranquil outdoor environment.

Guesthouse in Boerne

5 out of 5 average rating, 57 reviews

Pleasant Valley Hideaway

Welcome to our charming 1-bedroom retreat, nestled on tranquil acreage with stunning sunsets and peaceful nights. Located in the picturesque town of Boerne, our getaway offers the perfect blend of small-town charm and modern comforts, with easy access to the vibrant downtown San Antonio, the scenic Fredericksburg and the many Texas state parks (Guadalupe River State Park is 12-minutes away).

Guest favorite

Cabin in Fredericksburg

4.95 out of 5 average rating, 199 reviews

Beautiful Hill Country Views | Studio Cabin

Welcome to The Holiday! The Holiday is a quaint cabin comprised of handmade craftsmanship, local findings and owner-created artworks. The Holiday is a hilltop cabin located on 16 acres of beautiful untouched land with vast panoramic views! Enjoy the serenity of a remote retreat while located only 15 miles from Fredericksburg Main Street and 10 miles from Luckenbach.

Guest favorite
A charming cottage is framed by mature trees, featuring a light green exterior and a welcoming porch with a wooden railing. The entrance is marked by a white door, inviting guests into a peaceful retreat. Surrounding greenery adds to the serene atmosphere.

Guesthouse in Comfort

5 out of 5 average rating, 22 reviews

Zen Comfort

This peaceful and centrally located cottage is sure to please. Private entrance to your own space. Located off High St., withing .5 mile walk of downtown, beautiful sunsets, mature trees, hot tub, and outdoor seating. The home has 1 bedroom with Queen bed, a twin room, and Queen couch pull out. It's time to slow down and relax in the present moments in life.

Guest favorite
A spacious outdoor area features a circular firepit surrounded by several black wooden chairs. The landscape is open, showcasing dry grass and distant hills under a clear blue sky, offering an inviting space for gatherings and relaxation.

Home in Boerne

4.86 out of 5 average rating, 50 reviews

Hochland Haus Hill Country Views

Escape to Hochland Haus a serene three bedroom home situated on 2-acres. With a firepit, cornhole, and stunning views this home is perfect for families and friends to gather. Situated halfway between Fredericksburg and Boerne, makes it the perfect place to discover the Texas Hill Country.

Popular amenities for Kendall County vacation rentals

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