Vacation rentals with a pool in Kendall County

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.

4.99 out of 5 average rating, 152 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.

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.

4.96 out of 5 average rating, 27 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 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

4.9 out of 5 average rating, 196 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!

4.98 out of 5 average rating, 44 reviews

The front exterior of the home is showcased, featuring blue siding and a white door. Large windows are framed with greenery from nearby trees, providing a sense of connection to nature. A pathway leads from the entrance to the sidewalk.

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)

Guest favorite

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, 139 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.

5 out of 5 average rating, 216 reviews

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

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, 84 reviews

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

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

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, 6 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.

4.97 out of 5 average rating, 173 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

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

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, 71 reviews

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

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, 106 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.

Vacation rentals for every style

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Convenient locations with everyday essentials

Popular amenities for Kendall County rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A landscaped yard features a winding pathway leading to a spacious pool area, surrounded by greenery. Lush trees provide shade, while a patio table and chairs are positioned nearby. The setting includes a peaceful atmosphere, ideal for relaxation amidst the natural surroundings.

Home in Comfort

4.67 out of 5 average rating, 45 reviews

Hilltop Retreat

WilliamRating, 5 stars2 weeks ago

Great, get away from it all and close to town... Very spacious and eclectically furnished. We hosted a family get together prior to a wedding and there was lots of room for people to visit. The pool was great for our grandchildren. Would definitely stay there again.

DerekRating, 5 stars23 months ago

A charming cottage is nestled among mature trees, with a gravel path leading to its welcoming entrance. The building features a gabled roof and a spacious front porch, shaded by branches. Natural light filters through the foliage, enhancing the peaceful outdoor setting.

Home in Boerne

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.

4.67 out of 5 average rating, 6 reviews

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

Boerne Hacienda with Pool and Spa

MorganRating, 5 stars1 month ago

Amazing place, Sean was response and helpful!

5 out of 5 average rating, 4 reviews

An aerial view of an oval swimming pool is presented, surrounded by lounge chairs and umbrellas featuring green and white stripes. Lush greenery lines the edges, enhancing the serene environment.

Home in Comfort

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

AlyssaRating, 5 stars10 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

A private swimming pool and hot tub are set within a landscaped outdoor area, surrounded by lush greenery. The pool features natural stone accents, and relaxing lounge chairs are positioned nearby. A modern house with large windows overlooks the serene setting.

Home in Pipe Creek

Rockin' B Ranch | Summit | Texas | Vacation

DeborahRating, 5 stars14 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.

4.85 out of 5 average rating, 80 reviews

A serene salt-water pool glistens under clear blue skies, surrounded by lush greenery and trees. Lounge chairs are placed nearby, and a fire pit is visible in the background, providing a tranquil outdoor space for relaxation.

Home in Kendall County

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

YeimiRating, 5 stars3 weeks ago

My family and I had a great Mother's Day weekend in Kristen & Jeff's lovely home. It is very spacious! Very clean and the backyard is beautiful! We enjoyed the pool, BBQ grill and the patio furniture. Highly recommend it! Guadlupe River Staye Park is near by as well. Thank you!

4.95 out of 5 average rating, 82 reviews

A tranquil outdoor space features a sparkling pool surrounded by natural landscaping, with lush trees providing shade. A playful inflatable swan floats on the water, and comfortable sun loungers are positioned nearby on a stone terrace, inviting relaxation in a serene atmosphere.

Home in Bulverde

Bulverde's Gem | Pool & Gazebo & Mini Horses

LucilaRating, 5 stars2 weeks ago

Our vacation at Yaya’s was an amazing experience. Thank you Yaya for being an incredible host! A great host makes all the difference in an airbnb stay. Thank you Paula too! It’s a rare opportunity to stay at a house so pristine! Immaculately clean and elegantly decorated with such detail and care. This place is cherished and you can feel it since the moment you arrive at such a well maintained and comfortable environment! The property is furnished with beautiful quality furniture, beds, linens. The kitchen is also a 100% percent equipped, we stayed for a week and cooked all our meals without missing any tools to prepare them. We really enjoyed the pool, grilling, visiting the pony’s area, the games at the garage, walking around the property, the trees, watching some deer in the afternoon. It was the best place to build memories together as a family and we are grateful.