Holiday rentals with a pool in Timberwood Park

4.99 out of 5 average rating, 188 reviews

Home in Spring Branch

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.

LocationFamilyRiver

An open-concept living area features stylish furnishings, including a large sectional sofa with decorative pillows. Natural light floods the space through multiple windows, highlighting the sleek dining area and modern kitchen in the background. Unique light fixtures add character to the inviting atmosphere.

4.97 out of 5 average rating, 234 reviews

Nice Oasis in N Central San Antonio w/ Heated Pool

Relax at our fully remodeled home conveniently located off 1604 and 281. Just 20 minutes from The Pearl, Downtown, Six Flags, La Cantera & the airport. Spend your days exploring San Antonio and then lounge by the pool or play basketball. Either way we hope you create lifelong memories! This home is perfect for any and all travelers to spread out and enjoy all that San Antonio has to offer. Note: pool heater is OFF during warmer months and ON during cooler months. No additional charge for heater

ValueFamilyTV

An inviting backyard oasis features a sparkling pool with a built-in spa, surrounded by a stone patio. Several lounge chairs are positioned nearby, and decorative planters add greenery. A fence provides privacy, while the clear blue sky creates a bright and open atmosphere.

4.96 out of 5 average rating, 165 reviews

Elite Vacation Entertainment- 5 Stars (discounts)

A luxurious new five-star home in the Northside of San Antonio is now available.This property boasts 4 bedrooms and 2.5 bathrooms, including a master bedroom, a spacious open kitchen, a living room, a dining area, a theater room, a washer/dryer, and a lounge.The second story features three guest rooms and a full bathroom. The backyard is a true paradise, featuring a pool, spa,lounging bar with TV, relaxing cabana, and a grill for cooking. Additionally, there is a four-car parking lot driveway.

LocationValueAir conditioning

4.86 out of 5 average rating, 145 reviews

A spacious black leather sectional sofa defines the living area, accented by a plush throw blanket draped over one side. In the background, a modern kitchen is visible with dark cabinetry and stainless steel appliances, illuminated by soft natural light from nearby windows.

Home in Stone Oak

Gorgeous retreat w Hot Tub Lux Shower & Cabana

Experience upscale comfort in this fully renovated, luxurious 4BR/2BA home in beautiful Stone Oak. Relax in your private hot tub or unwind under the cabana. The $18K outdoor shower offers a spa-like experience with powerful body jets. Inside, the primary bath features a custom 6-jet shower for total rejuvenation. Enjoy immersive music with the Sonos sound system, cook in a modern kitchen, and soak up the sun at a sparkling nearby resort-style pool—ideal for fun or pure relaxation.

ValueFamilyHot tub

4.94 out of 5 average rating, 103 reviews

The Treehouse At La Cantera | 5 Min to Six Flags

Discover your perfect San Antonio escape! Enjoy our home with an above-ground pool set against Texas Hill Country views, yet only minutes from Six Flags, Fogo De Chao & Brazao, Top Golf, The Rim, and The Award Winning La Cantera Mall. Ideal for relaxation or adventure, this spot offers a unique blend of privacy in a treehouse setting with access to the best of North San Antonio in the tight-knit neighborhood of Legend Hills. Perfect for any family getaway!

FamilyValueIndoor spaces

4.95 out of 5 average rating, 194 reviews

Villa in San Antonio

Hill Country Views | Pool + Hot Tub | Sleeps 12

•Space to Gather, Views to Remember. •Scenic Vista is a spacious Hill Country retreat designed for families and groups who want room to spread out and enjoy time together. •Take in sweeping views, relax in the hot tub, cool off in the swimming pool, and enjoy a warm, comfortable home that sleeps up to 12 guests. •Perfect for family vacations, friend getaways, or celebrations, this property offers both privacy and space in a setting everyone will love.

LocationValueHospitality

4.94 out of 5 average rating, 128 reviews

A private heated pool is surrounded by a deck featuring a patio umbrella and comfortable seating. Scenic views of the hill country are visible in the background, with a clear blue sky overhead. The area offers space for relaxation and enjoyment.

Home in Canyon Lake

Cozy Cottage with heated pool and amazing views.

The Cozy Cottage is your ideal spot for relaxation and rejuvenation! It's nestled on a hilltop in a semi-secluded area of the Texas Hill Country. Escape to a warm, welcoming, and private, pet-friendly home offering all the comforts of cozy living. Located just minutes from restaurants, shopping, and Canyon Lake. Only 8 miles to the Guadalupe River and the Whitewater Amphitheater, and 19 miles to the charming town of Gruene. There's something for everyone!

ValueFamilyLong stay

4.97 out of 5 average rating, 123 reviews

Home in Bulverde

Hill Country LUX | Pool & Horses

Escape to a serene retreat on 8 picturesque acres, where peace and tranquility meet convenience. Despite the secluded feel, you’ll find popular spots like H-E-B, IHOP, Starbucks, Burger King, and Taco Bell just a 2-minute drive away. Enjoy easy access to local attractions, with the Guadalupe River just 15 minutes away, and New Braunfels and Canyon Lake only 25 minutes from the property. Plus, the San Antonio Airport is just a short 25-minute drive

ValueLocationShared spaces

4.96 out of 5 average rating, 192 reviews

Villa in Bulverde

Cibolo Chase private resort w/hot tub & pool

Discover a rare luxury escape where privacy, elegance, and natural beauty converge. Set on 11 secluded acres in the heart of the Texas Hill Country, The Villa at Cibolo Chase is an exclusive retreat designed for guests seeking refined comfort, open space, and complete tranquility. Just 25 minutes north of San Antonio along Highway 281, this hidden sanctuary feels worlds away while remaining close to the region’s finest destinations.

LocationFamilyBackyard

4.97 out of 5 average rating, 200 reviews

Casa Bella Hideaway Retreat with Pool

Forget your worries in this serene space. Our home is ready to give you a “retreat” experience outside of the city with a hill country flavor, and close enough to enjoy the restaurants and shopping centers in the city. Full of trees and wildlife. Enjoy the pool and many secret places to watch the sunset with cup of coffee or a glass of wine. If you are a golfer we are near to Canyon Springs Golf Club, Sonterra and PTC Golf Club.

ValueFamilyParking

4.97 out of 5 average rating, 216 reviews

Guesthouse in Boerne

Hill Country Outdoor Retreat | Bluebonnet Oasis

Modern country guest house just 4 miles from Downtown Boerne with easy access to San Antonio and the Hill Country. Built in 2020, it features 2 spacious bedrooms, a granite kitchen with a large island, and an open-concept layout. Relax with a 75” 4K TV or enjoy the front porch. Step outside to a large shared pool, shaded seating, and firepit—shared only with one other guesthouse. Perfect for a weekend getaway or extended stay.

ValueFamilyCheckout