Holiday rentals with a pool in Kendall County

Find and book unique homes with a pool on Airbnb

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Popular amenities for Kendall County rentals with a pool

House rentals with a pool

Guest favourite
Home in Fredericksburg
4.93 out of 5 average rating, 28 reviews

Bamma’s Bluebonnet

RyanRating, 5 stars2 weeks ago
We had a great stay at this charming two-story country home just outside Fredericksburg. The house was clean, quiet, and had everything we needed for a relaxing getaway. The host was very responsive and accommodating — they even allowed us to check out a little later than planned, which we really appreciated. As a bonus, they provided us with coupons to some of the local wineries, which made exploring the area even better. Would definitely stay here again!
Top guest favourite
Home in Boerne
5 out of 5 average rating, 8 reviews

Hill Country Views at The Oval at Owl Spring Ranch

QuintenRating, 5 stars1 day ago
Such a cute and fabulous place. Janet was awesome and super friendly and made us feel right at home. 10/10 would stay again
Guest favourite
Home in Boerne
4.87 out of 5 average rating, 39 reviews

The Not So Ugly Duckling

JamieRating, 5 stars3 weeks ago
Tara was very responsive and helpful. She took care of everything promptly. The house was very well equipped and the kitchen was new, clean and well stocked. The pool was clean and nice. Easy to walk everywhere on Main St in Boerne and River Rd. Excellent stay!
Superhost
Home in Comfort
5 out of 5 average rating, 4 reviews

3-bedroom House at The Meyer Hotel w/ Creek View

AlyssaRating, 5 stars11 months ago
We enjoyed our stay at this property while passing through on a family vacation. It was exactly what we were looking for—clean, spacious, and full of history. The location itself was beautiful, like a little piece of art. We would definitely like to come back and stay again. We plan on booking this place on our next trip this way. It’s a hidden gem that you should see. The pool and bar were nice, and the host provided great food recommendations. They were super helpful and made sure we were well taken care of. 5 Star review all the way!
Superhost
Home in Pipe Creek
4.85 out of 5 average rating, 46 reviews

Rockin B Summit | Luxury Retreat with Pool & Creek

DeborahRating, 5 stars15 months ago
The ranch house was perfect for our family gathering. We all had plenty of room for private moments and plenty of shared space for gathering, gaming, cooking and meal-sharing. The Grandkids loved the pool, pool table and especially the chickens! Our family highly recommends Rockin B Ranch.
Top guest favourite
Home in Kendall County
4.85 out of 5 average rating, 81 reviews

7-Acre Hill Country Haven w/ POOL-Guadalupe River

KylieRating, 5 stars3 weeks ago
Everything we were looking for in a place to stay and enjoy some time pool side.
Top guest favourite
Home in Bulverde
4.95 out of 5 average rating, 86 reviews

Luxury Escape • Pool • Gazebo • Mini Horses

DevonRating, 5 stars1 week ago
This was the best Airbnb I have stayed at. The host was super welcoming and was very responsive. The place was so clean and ready for anything we wanted to do. We enjoyed our stay and will definitely be booking again. The property was well worth the money. 10/10 recommend. Thank you Yaya for such an amazing stay.
Top guest favourite
Home in Boerne
5 out of 5 average rating, 16 reviews

Hill Country Guest House w/Pool on 5 gated acres!

Colleen MarieRating, 5 stars1 day ago
We had a wonderful family vacation here and couldn’t have asked for a better place to relax and reconnect. The guest house had plenty of space for our group of 8 adults and 2 children—everyone was comfortable and had room to spread out. The grounds were absolutely beautiful and perfect for spending time outdoors. We especially enjoyed the Argentina-style fire pit in the evenings and the serene, well-kept pool during the day. This spot is a true escape into the peaceful Texas Hill Country. A perfect setting to unwind, take in the scenery, and enjoy family time. Highly recommend for anyone looking to slow down and soak in nature with loved ones.

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