
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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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.

GWR-FBG|Private|Hilltop|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 area great for star gazing, hiking and explore the property or just make memories around the fire pit.

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.

The Longhorn
Introducing The Longhorn Suite at Grape Creek Country Cottages, an adults only retreat! Enjoy the peaceful country setting that GCCC has to offer. Take a ride to Bankersmith,TX or Grapetown Vineyard on our fat-tire E-bikes and cool off in our sparkling clean pool! The suite is equipped with a queen bed, large kitchenette, private BBQ, walk-in shower bath and outdoor fire-pit to kick back under the starry TX nights. Located only 15 minutes from Main St. Fredericksburg and the 290 Wine Corridor.

Tapatio Springs Resort, Boerne. Relax, Dine, Golf
Ready for your relaxing Texas Hill Country escape? This top-floor, luxury 2 bedroom / 2 bathroom condo has the most magnificent views of Tapatio Springs Resort! It overlooks the pool as well as the beautifully maintained 18 hole golf course. Grab a coffee, beer or glass of wine & enjoy the heavenly views from the 2 balconies. Your Bnb is just a short stroll to the swimming pool, golf clubhouse and La Cascada Table & Bar. Enjoy dinner, drinks & live music! (Only 10 minutes to downtown Boerne!)

3/2, Private hot tub, fireplace, firepit
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!

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.

Our Texas Hill Country Retreat
Welcome to Our Texas Hill Country Retreat! Escape to our cozy getaway, perfect for families or groups. The home features: 1 Queen Bed 2 Full Beds 2 Twin Beds Relax in the beautiful backyard oasis, where you’ll create unforgettable Hill Country memories! We’re perfectly located just 15 minutes from Downtown Boerne and 25 minutes from The Rim, La Cantera, and Six Flags — so you’re close to shopping, dining, and family fun. Book your stay and experience the charm of the Texas Hill Country!

Private 2BR Amazing Views, Firepit, Peaceful
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

3 Acres, Pool, Views, Kiva Fireplace
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" !

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!

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.
Popular amenities for Kendall County rentals with a pool
House rentals with a pool

Hilltop Retreat

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

The Not So Ugly Duckling

3BR House | Creek View | Pool | The Meyer Hotel

Rockin B Summit | Luxury Retreat with Pool & Creek

Bulverde Hill Country Ranchette | Horses + Pool

Hill Country Gem with pool

Hill Country Guest House w/Pool on 5 gated acres!
Other vacation rentals with a pool

House w/ Airstream | Cabin | Plunge Pool | Firepit

Pond House Bungalow at Bergheim Ranch

Bamma’s Bluebonnet

8/4, private pool, 2 hot tubs, wine trail

The Lonestar

Haven River Inn Buttercup Cottage

Butterflies Cabin @ HomeAway Ranch

Tree House Bungalow @ Bergheim Ranch
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- San Antonio River Walk
- Six Flags Fiesta Texas
- Alamodome
- Frost Bank Center
- Blue Hole Regional Park
- Natural Bridge Caverns
- Pearl Brewery
- Tobin Center For the Performing Arts
- Guadalupe River State Park
- Morgan's Wonderland
- Pedernales Falls State Park
- San Antonio Botanical Garden
- Canyon Springs Golf Club
- Hamilton Pool Preserve
- Blanco State Park
- San Antonio Missions National Historical Park
- SeaWorld San Antonio
- Natural Bridge Wildlife Ranch
- Government Canyon State Natural Area
- Wimberley Market Days
- McNay Art Museum
- The Bandit Golf Club
- Tower of the Americas
- Jacob's Well Natural Area




