Vacation rentals with a pool in Kendall County

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Top-rated rentals with a pool in Kendall County

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

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Guest favorite

Home in Spring Branch

4.99 out of 5 average rating, 148 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.

Guest favorite

Home in Fredericksburg

5 out of 5 average rating, 206 reviews

GWR-Private-AmazingViews-HotTub-Stars-FirePit-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.

Guest favorite

Rental unit in Boerne

5 out of 5 average rating, 18 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.

Guest favorite

Guesthouse in Kendall County

5 out of 5 average rating, 163 reviews

Whimsy Hill Treetop Retreat w/ Hill Country Views

The Whimsy Hill Treetop Retreat is a quaint single bedroom upstairs apartment located in the countryside of the beautiful Hill Country. Completely renovated, and positioned high among the trees, this cottage has all the amenities and comfort you would want for your hill country visit. Sit on the front deck or covered downstairs patio and enjoy miles of amazing Texas Hill Country views. Hang out and take a plunge in the resort style swimming hole with waterfall or enjoy a soak in the hot tub.

Guest favorite

Home in Spring Branch

4.94 out of 5 average rating, 18 reviews

Resort Style S/W Home, Views & Pool

Designer home on 3 acres just 15 minutes from Guadalupe State Park. Close to Park 31 and The Lost Mission Wedding Venues. Resort style living with huge windows to enjoy the beautiful views, soaring skylights, designer imported counters and a stone bathroom. There is so much to do in the area.... swimming or kayaking on the river or at Canyon Lake (Kayaks provided) or spend the day out at the beautiful wineries nearby in the Texas Wine Country. We're in "The Gateway to the Hill Country".

Guest favorite

Tent in Fredericksburg

4.9 out of 5 average rating, 110 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 favorite

Home in Boerne

4.89 out of 5 average rating, 18 reviews

250 Acre Ranch on Guadalupe River w/ Pickleball!

(Pickeball!) We are delighted to offer our family's 250 acre private ranch for your family. Enjoy a wonderful adventure at the Poco Loco Ranch - breathtaking land, nestled in the Texas Hill Country (near Boerne) with 1/4 mile exclusive access to the Guadalupe River. Included is a historic 19th century ranch house, large private pool, cabana guest house & separate kitchen and enormous game room. Private roads & river access allow for amazing tubing and hiking & a NEW Pickleball Court!

Guest favorite

Cabin in Kendalia

5 out of 5 average rating, 67 reviews

Secluded 29 Acres, Epic Views, FirePit, Privacy

Unwind at your secluded Ranchette in Kendalia, TX! 1.5 hours from Austin, this luxurious retreat offers an incredible experience for 4 guests. Set atop 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!

Guest favorite

Guesthouse in Boerne

4.97 out of 5 average rating, 168 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.

Guest favorite

Home in Blanco

4.92 out of 5 average rating, 167 reviews

Modern 3/2 (two kings), hot tub, fire pit, 16min t

Experience Texas Wine Country's allure in our new 3 bed / 2 bath retreat, steps from Blanco's square. Explore renowned 290 Texas Wine Trail between nearby Fredericksburg and Johnson City, relax at Blanco River State Park, and visit attractions like Canyon Lake and Enchanted Rock. Enjoy our backyard oasis with a hot tub and dining area under a pecan tree. Sleep soundly in our king beds and queen accommodations. Book now for an unforgettable Hill Country escape!

Guest favorite

Cabin in Spring Branch

5 out of 5 average rating, 56 reviews

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.

Guest favorite

Home in Spring Branch

5 out of 5 average rating, 105 reviews

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.