Vacation rentals with a pool in Kendall County

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Top-rated rentals with a pool in Kendall County

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Top guest favorite

The image showcases a private guesthouse set above a custom pool with a spa, surrounded by lush greenery. The two-story home features a covered balcony and large glass doors, allowing for natural light to fill the space. The pool area includes stone steps leading into the water.

Home in Spring Branch

4.99 out of 5 average rating, 155 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.

Superhost

An inviting outdoor area features a clear swimming pool surrounded by comfortable lounge chairs, each topped with turquoise cushions. A patio is equipped with large umbrellas, and a stone pathway leads towards an outdoor kitchen space, enhancing the entertaining potential of the setting.

Home in Boerne

4.7 out of 5 average rating, 10 reviews

Boerne Hacienda with Pool and Spa

The timeless architecture features an open floor plan, marble floors, exposed ceiling beams, his and hers master bath suite, chef's gourmet kitchen with wolf sub-zero appliances and wood burning pizza oven. The back patio is perfect for entertaining or relaxing with your favorite beverage and is only a few steps away from the beautiful crystal-clear pool built summer of 2023! Please no events or parties. The house is located in a residential neighborhood so please observe outside quiet hours

Top guest favorite

An oval-shaped house features a corrugated metal exterior with multiple windows allowing natural light. A vibrant red door adds a pop of color. Several chickens are seen roaming nearby, adding a touch of rustic charm to the peaceful outdoor setting.

Home in Boerne

5 out of 5 average rating, 10 reviews

Hill Country Views at The Oval at Owl Spring Ranch

During your stay at The Oval House experience the peace and quiet of the beautiful Texas Hill Country. Enjoy starlit nights by the pool and lazy days watching cows mosey by or an occasional visit by a curious chicken or two. White tail and Axis deer generally come out in the evenings or early mornings. The Guadalupe River is minutes away. With the quaint town of Boerne being a 20 minute drive and the city life of San Antonio or charming Fredericksburg and its many wineries only 20 minutes more.

Guest favorite

A spacious living area is highlighted by large windows allowing natural light to fill the room. Comfortable seating is arranged around a smart TV, while a modern kitchen island with bar stools offers an inviting space for dining and socializing.

Home in Blanco

4.91 out of 5 average rating, 214 reviews

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!

Superhost

A canvas tent with an open entrance reveals a spacious interior featuring a king-size bed dressed in crisp linens. Outside, a private hot tub sits adjacent to a wooden deck, which is complemented by a hammock chair hanging from a nearby tree, surrounded by natural greenery.

Tent in Fredericksburg

4.88 out of 5 average rating, 149 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.

Top guest favorite

A serene view of the hilltop cabin is captured at dusk, showcasing a spacious deck with seating areas and red umbrellas. The cowboy pool is visible nearby, and the cabin’s warm lights create a welcoming atmosphere against the backdrop of the natural landscape.

Home in Fredericksburg

5 out of 5 average rating, 222 reviews

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.

Top guest favorite

A seasonal stock tank pool is set against a backdrop of rolling hills and expansive greenery, inviting relaxation under a clear blue sky. The natural landscape stretches into the distance, providing a serene and tranquil atmosphere.

Cabin in Kendalia

5 out of 5 average rating, 96 reviews

Peaceful 2BR 29 Acres, Epic Views, Pool, Privacy

Escape to your peaceful 2BR/2BA private 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

Guest favorite

A charming two-story structure is illuminated at dusk, surrounded by landscaped gardens. The building features multiple balconies and is accessible by a wooden staircase. Soft outdoor lighting highlights the pathways and greenery, creating a serene evening atmosphere.

Home in Blanco

5 out of 5 average rating, 7 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 favorite

A large private pool is surrounded by natural landscaping, featuring a stone wall and lush plants. The home, designed with outdoor relaxation in mind, is visible in the background, showcasing large windows and a spacious deck with seating.

Home in Spring Branch

4.97 out of 5 average rating, 36 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 in "The Texas Wine Country" (about 45 min up Hwy 281). We're in "The Gateway to the Hill Country" !

Guest favorite

Three wooden chairs are arranged on a wooden deck, facing an expansive night sky filled with clouds and stars. A warm glow emanates from the window of the nearby cabin, creating a serene atmosphere.

Tiny home in Fredericksburg

4.94 out of 5 average rating, 17 reviews

Scenic Hill Cabin: Trails & Cows in Fredericksburg

Welcome to Your Texas Hill Country Retreat Escape to nature and indulge in serenity at this charming retreat nestled in the heart of the Texas Hill Country. This cozy cabin, ideal for up to four guests, offers a perfect blend of comfort and a true outdoor experience. Located just under an hour and a half from both Austin and San Antonio. Near Enchanted Rock State Natural Area: Experience the natural beauty and geological wonders of one of Texas's most beloved parks.

Superhost

A charming windmill cottage is nestled among large trees, featuring a dark exterior and a metal roof. A welcoming porch invites guests to enjoy the outdoor space, with a landscaped area visible in the foreground, highlighted by a natural stone sign.

Home in Kendall County

4.94 out of 5 average rating, 66 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 favorite

The historic cabin features a rustic exterior with a red roof and preserved logs. Surrounding it are mature oak trees and an open yard with a fenced area. A dog wanders in the foreground, adding to the peaceful rural setting.

Cabin in Spring Branch

5 out of 5 average rating, 75 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.