
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.

Home in Boerne
5 out of 5 average rating, 75 reviewsFirefly 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!

Home in Fredericksburg
4.88 out of 5 average rating, 164 reviewsTwilight 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.

Cabin in Fredericksburg
4.99 out of 5 average rating, 185 reviewsRanch 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 suite in Pipe Creek
4.96 out of 5 average rating, 150 reviewsMadrona 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!

Home in Boerne
5 out of 5 average rating, 40 reviewsCottage 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.

Home in Comfort
4.98 out of 5 average rating, 175 reviewsHigh 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

Home in Boerne
4.86 out of 5 average rating, 63 reviewsThe 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.

Home in Boerne
4.83 out of 5 average rating, 30 reviewsThe 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!!

Guesthouse in Boerne
5 out of 5 average rating, 57 reviewsPleasant 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).

Cabin in Fredericksburg
4.95 out of 5 average rating, 199 reviewsBeautiful 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.

Guesthouse in Comfort
5 out of 5 average rating, 22 reviewsZen 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.

Home in Boerne
4.86 out of 5 average rating, 50 reviewsHochland 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.
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Popular amenities for Kendall County vacation rentals
Other great vacation rentals in Kendall County

Home in Blanco
4.96 out of 5 average rating, 28 reviews3 bedrooms, huge backyard, <.5Mi Blanco St Park

Home in Spring Branch
4.97 out of 5 average rating, 144 reviewsLodge, Hot Tub, Pool, Epic View, and much more!

Home in Spring Branch
4.94 out of 5 average rating, 325 reviewsCasita on the Ranch 2,wildlife,sunsets,stars,relax

Cottage in Boerne
4.88 out of 5 average rating, 82 reviewsPerfect country-side get-away for 2-4+ people

Guesthouse in Bulverde
5 out of 5 average rating, 6 reviewsCozy Casita-Long, mid, or short term.

Home in Boerne
4.89 out of 5 average rating, 18 reviews250 Acre Ranch on Guadalupe River w/ Pickleball!

Cabin in Boerne
5 out of 5 average rating, 10 reviewsHill Country Cabin Escape!

Home in Spring Branch
4.95 out of 5 average rating, 19 reviews3 Acres, Pool, Kiva Fireplace, S/W Resort Style
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