Holiday rentals with a pool in Kendall County

4.99 out of 5 average rating, 153 reviews

Home in Spring Branch

Relax and Enjoy the Views of the Hill Country

Set on a cliff above the Guadalupe River this private guesthouse with sweeping vistas is your Hill Country getaway. This home was designed for guests rest, relaxation and fun. Conveniently located near shopping, dining and outdoor activities although you may never want to leave the peace and quiet. Set on a cliff above the Guadalupe River this private guesthouse with sweeping vistas is your Hill Country getaway. This home was designed for guests rest, relaxation and fun. Conveniently located near shopping, dining and outdoor activities although you may never want to leave the peace and quiet. Take in the incredible views of the river, ranch and Hill Country from the custom pool and spa. One of a kind Texas views in a truly unique home make this an unforgettable Hill Country destination. See this house in the just released book "Spectacular Weekend Getaways of Texas" by Jolie Berry of Signature Boutique Books. Cliff Haven on the Guadalupe. In the middle of nowhere and near everything sums up this home. Very close to local shopping and dining. This guest house is located on 2.5 acres over 65 feet away from the main house in a safe and quiet community in Spring Branch Texas. Use it as your launching pad to visit the Hill Country, New Braunfels and San Antonio or just stay and unwind. This home was designed and appointed for the absolute best stay. Relax in the pool, enjoy the spa, grill a steak and enjoy drinks next to the fire. - Private Pool and Spa - Private Courtyard with Stone Fire Pit and Outdoor Seating - Outdoor Grill - Fully Equipped Kitchen - "Texas Living Room" Air Conditioned Finished Garage with Full View Glass Door, Pool Table, Sofa, Dining Table and Chairs, 60" TV, Mini Fridge, Ice Maker and Full Bath - High Quality Bedding and Pillows W.O.R.D. Permit #L1442 Guests have complete access to the entire home. The pool and spa is also for the exclusive use of the guests. The house is a separate very private guest house of the main home 65 feet away from main home. I value my guests privacy but I'm always available to answer questions or fill you in on all the cool things to do around here. This home is in a very quiet neighborhood. It has a very country type feel with deer and other wildlife readily seen. Home is available by car only and there is no public transportation or Uber available. This home is located about 35 minutes from downtown San Antonio. There are many parks and river access areas near the house. It's a great place to bike and run with awesome hills and flats. Great local restaurants and bars nearby and within a short drive.

4.91 out of 5 average rating, 203 reviews

Home in Blanco

3/2 Modern Escape, hot tub, Blanco river/pool

Escape to a luxurious retreat in the heart of Texas Hill Country! Our beautifully remodeled 3-bedroom, 2-bathroom house in Blanco offers modern design and an open floor plan. Enjoy the tranquility of a dark sky community and easy access to the Blanco River State Park. Explore the nearby Fredericksburg and Johnson City Wine Trail, or venture to Pedernales Falls and Enchanted Rock. You're just a few minutes stroll away from the charm of Blanco's square where dining, grocery, and shopping await!

4.93 out of 5 average rating, 46 reviews

Home in Blanco

3 bedrooms, huge backyard, <.5Mi Blanco St Park

17min to famed 290 Wine Trail / near Fredericksburg 3 Bedroom home w/ Four Queen Beds 2 minute drive from Blanco River. Each room has dedicated Mini-Split A/C Fast 200Mb WiFi Easy access to 290 wine trail; 16min to closest winery! 2 blocks from Blanco Town Square w shops & restaurants 0.5 Miles to Blanco State Park River Access / natural pool Fully stocked kitchen Washer and dryer Pets OK (fee) Garage parking that includes Level 1 EV Charger (bring your own charging cables & connectors)

4.88 out of 5 average rating, 142 reviews

Tent in Fredericksburg

Cherry Cove Glamping W/ Hot tub AND Cowboy Pool!

Welcome to Cherry Cove! Cherry Cove is luxury glamping at its best, located just 15 miles south of downtown, our tent includes a king size bed, A/C, en-suite bathroom with toilet and walk-in shower, private hot tub, your own cowboy pool, coffee, wifi, and more. Relax outdoors, take a nap in your hammock chairs, indulge in a soak in your private hot tub or snuggle in bed while you watch a movie on your projector. Cherry Cove has everything you'll need for a relaxing stay in the hill country.

5 out of 5 average rating, 218 reviews

Home in Fredericksburg

GWR-Private-HilltopViews-57AcWildlife-HotTub-Pool

Escape the Ordinary! Fredericksburg BNB with amazing views at our hilltop home on 57 ac is yours to experience all to yourself! Romantic and secluded with Grand Views in all directions. Perfect for a "getaway from it all". Just a short drive to Main Street shops and wineries. This is home away from home w/Starlink internet. Soak in our luxurious hot tub, cool off in the cowboy pool, dark sky great for star gazing, hike and explore the property or just make memories around the fire pit.

5 out of 5 average rating, 86 reviews

Cabin in Kendalia

Peaceful 29 Acres, Epic Views, Pool, Privacy

Escape to your peaceful 2BR/2BA secluded Ranchette in Kendalia, TX! 1.5 hours from Austin, this luxurious retreat offers an incredible experience with rolling hills, you'll be mesmerized by the epic panoramic views that stretch as far as the eye can see! Indulge in the ultimate rustic relaxation with your seasonal stock tank pool, or firepit in the cold months, with breath-taking views while you soak up the Texas sun. At 29 acres, this cabin offers complete privacy and tranquility

5 out of 5 average rating, 6 reviews

Home in Blanco

Will's Tree House- Artful 1 Bed with Outdoor Bar

Come visit the ranch getaway of your dreams. The views and the cowboy vibes are unbeatable. Come for a romantic getaway or a solo visit for rest and relaxation. Enjoy coffee on the balcony or a beverage at the outside patio in the trees. Rest up in the handmade bed from African acacia trees or sunbathe at the pool! Have a little fun playing cornhole or relax in the hot tub. This house is sure to delight and comfort you! Enjoy our SHARED pool and hot tub with only 1 other house.

4.96 out of 5 average rating, 28 reviews

Home in Spring Branch

3 Acres, Pool, Kiva Fireplace, S/W Resort Style

Designer home on 3 acres just 15 minutes from Guadalupe River State Park. 33 minutes from Canyon Lake or Downtown San Antonio. Close to Park 31 and The Lost Mission Wedding Venues. Resort style living with huge windows to enjoy the beautiful views, soaring skylights, imported counters and a stone bathroom. There is so much to do in the area..swimming, tubing, wine tasting in "The Texas Wine Country" (about 45 min up Hwy 281). We're in "The Gateway to the Hill Country" !

4.97 out of 5 average rating, 175 reviews

Guesthouse in Boerne

Boerne Ranch Style guesthouse

Country guest house, located 4 miles from Downtown Boerne with easy access to San Antonio and surrounding hill country. Built in 2020, 2 spacious bedrooms, granite kitchen with a huge island and an open concept floor plan. Enjoy a 75" 4k tv with all streaming channels or relax on the front porch. Perfect for a weekend or extended stay. Step outside to the firepit or swim in huge pool with lots of shaded seating and tables, shared only between the 2 guesthouses.

4.95 out of 5 average rating, 62 reviews

Home in Kendall County

Windmill House -Guest Cottage w/pool in Texas Hill Country

Come enjoy our Cozy Windmill Cottage Guest House with refreshing shared pool (shared by 3 ranch homes) right outside your door in the Texas Hill Country. The house has been gently restored and offers 3 bedrooms and 3 baths to accommodate large groups. If scenic views and starry nights are your cup of tea then come for a visit. Or if you are visiting friends and family or attending a wedding at one of the many area venues come enjoy some time at the Ranch!

5 out of 5 average rating, 73 reviews

Cabin in Spring Branch

Historic Hideaway.

1846 Secluded, Restored Cabin on 40 acres with Modern Finishes Take life easy at this historic cabin uniquely restored for comfort and rest. Cabin is 1/4 mile from quiet county road and has expansive ranch behind it. Quiet country living at its best. When ready for adventure, we are centrally located being forty minutes from Gruene, Fredericksburg, Marble Falls, and San Antonio! Put -in for the Upper Guadalupe is only 10 minutes away.

5 out of 5 average rating, 109 reviews

Home in Spring Branch

NEW! - The Texas River Property

8+ acres of private, water front property with a beautiful home that is all yours for the duration of your rental . This property boasts river access immediately on property, just walk right on down to the Guadalupe and set your chairs up to enjoy a day in the cool flowing waters of one of Texas's finest rivers. The acreage offers open land to run and play on and explore all around. Check out the photos and message us with any questions.

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House rentals with a pool

DerekRating, 5 stars23 months ago

Delux Cottage in the Woods w/ Jacuzzi

Beautiful property that was inviting, quiet, and personable. We loved the time we spent. The lighting was impeccable and placed us in a wonderful atmosphere.

4.93 out of 5 average rating, 28 reviews

Home in Fredericksburg

Bamma’s Bluebonnet

RyanRating, 5 stars1 week 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!

5 out of 5 average rating, 7 reviews

Hill Country Views at The Oval at Owl Spring Ranch

RandyRating, 5 stars1 month ago

This has been one of my favorite Airbnb stays. Personally loved the peace and quiet of being out in the hills. The house was spotless and unique. Our son loved the pool and the frequent visits from the chickens. Overall a wonderful stay.

4.87 out of 5 average rating, 39 reviews

The Not So Ugly Duckling

JamieRating, 5 stars2 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!

5 out of 5 average rating, 4 reviews

Home in Comfort

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!

4.85 out of 5 average rating, 46 reviews

Home in Pipe Creek

Luxury Hill Country 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.

4.95 out of 5 average rating, 85 reviews

Home in Bulverde

Bulverde's Gem | Pool & Gazebo & Mini Horses

DevonRating, 5 stars3 days 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.