Holiday rentals with a pool in Kendall County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Kendall County

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

0 of 0 items showing

1 of 3 pages

Top guest favourite

Home in Spring Branch

4.99 out of 5 average rating, 151 reviews

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.

Top guest favourite

Home in Fredericksburg

5 out of 5 average rating, 214 reviews

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

Escape the Ordinary! Million dollar views from this hilltop cabin on 57 acres 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 the luxurious hot tub or in the cowboy pool under the Texas sky, star gaze, ride the trails in the Kawasaki Mule, hike and explore or just make memories around the fire pit.

Top guest favourite

Home in Spring Branch

4.96 out of 5 average rating, 25 reviews

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 at "The Texas Wine Country" (about 45 min up Hwy 281). We're in "The Gateway to the Hill Country". Or enjoy our "resort".

Guest favourite

Home in Blanco

4.94 out of 5 average rating, 301 reviews

5/2 (two kings), fireplace, hot tub, firepit

**Now offering 4+ night stay discounts** Experience Texas Wine Country luxury at our updated retreat near Blanco's charming square. With 5 bedrooms (w 2 king beds) and 2 bathrooms, our retreat is ideal for cozy getaways or gatherings up to 16. Cozy up to the new electric fireplace mantel in the living room, relax in the bubbling hot tub, gourmet kitchen, and a fire pit to enjoy the stars under the Texas Dark Sky Community. Explore wineries, rivers, and family attractions nearby. Enjoy opulent

Top guest favourite

Flat in Boerne

5 out of 5 average rating, 19 reviews

Luxurious Golf Resort Condo hosted by Angela

Whether you golf or not, you will love to relax with the family at this luxurious, peaceful condo in the midst of this stunning golf resort. Located in the beautiful Texas Hill Country, this 2 bedroom, 2 bath unit offers impeccable views! Just a very short walk to the amazing restaurant, cafe/gift shop, clubhouse, and pro shop. Relax on one of the two patio balconies that overlook the putting green/driving range. The condo features a rustic, at-home feel as soon as you step inside. 3 Roku TV's.

Top guest favourite

Home in Blanco

4.97 out of 5 average rating, 38 reviews

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)

Top guest favourite

Home in Boerne

5 out of 5 average rating, 14 reviews

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

Come visit the Texas Hill Country and stay in this huge completely renovated 3000 Sq Ft 2 story Guest House with Pool on 5 Gated Acres. We have two large living areas, 4 bedrooms-1 King, 1 Queen and two twin-over-full bunk beds, 2 Full bathrooms (and an outdoor shower!) and fully equipped kitchen. Right outside your door is a pool and spa. Relax by the fire pit and cook some 'smores. Amenities include 3 Flat screen TVs, wifi, washer/dryer, trampoline, play fort, BBQ grill, plenty of parking

Guest favourite

Tent in Fredericksburg

4.89 out of 5 average rating, 133 reviews

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.

Guest favourite

Home in Blanco

5 out of 5 average rating, 5 reviews

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.

Top guest favourite

Guest house in Boerne

4.97 out of 5 average rating, 171 reviews

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.

Superhost

Home in Kendall County

4.95 out of 5 average rating, 61 reviews

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!

Top guest favourite

Home in Boerne

4.97 out of 5 average rating, 58 reviews

Near everything but a true getaway, private pool

The Graham House is a COVID-free retreat in the heart of Boerne. This lovely, modern, clean house is a short walk from Main Street and a quick drive to numerous state parks, Comfort, Fredricksberg, the Guadalupe River and San Antonio. It offers an open floor plan with a modern kitchen. A beautiful place to get away! There is also a private pool in the backyard. It can be heated as long as the outside air temperature is above 50 degrees.