Vacation rentals with a pool in Comfort

4.96 out of 5 average rating, 260 reviews

A cozy sleeping area features a spacious bed with a light-colored quilt, accented by decorative pillows and a woven throw. Sunflower artwork brightens the wall above, while a small bedside lamp provides soft lighting. An air conditioning unit is positioned for comfort.

Tiny home in Comfort

Comfort Casita on a horse farm in the Hill Country

A cute cottage with a POOL on a working horse farm in the Texas Hill Country. Beautiful quiet setting close to Boerne, Fredericksburg shopping, dining and Wine Country, and San Antonio. River kayaking is close by and Comfort is an Antique shopping Mecca. The horses are friendly and complete the beautiful view out your front door. We are not a riding facility but love to share our beautiful farm with visitors looking for a peaceful holiday, convenient to lots of activities. Limit two guests.

A private in-ground pool is surrounded by a concrete deck featuring a shaded outdoor dining area. Several lounge chairs are arranged nearby, with splashes of water cascading from the pool's jets.

4.95 out of 5 average rating, 105 reviews

Close to Main- Pool, Hot Tub, Family Friendly

Located just off Main Street, Bell Street Bungalow is the perfect destination for a girls getaway, couple's retreat, or family weekend in Texas Wine Country. The home has 2 bedrooms, a bathroom, and game room in the main house in addition to a 1 bed/1 bath cottage in the backyard; both included in your stay. Enjoy the hill country outdoors by the private in-ground pool, hot tub, fire pit, and grill area. The home is a mile from the best downtown destinations and a short drive to many wineries.

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.

5.0 out of 5 average rating, 243 reviews

Welcome to Grandview Wildlife Ranch - A scenic hilltop hideaway on 57 private acres. GWR is your peaceful getaway in the Texas Hill Country. This private ranch setting is ideal for couples looking to unwind with expansive views, charming rustic interior and thoughtful amenities. The ranch is quiet and cozy and offers a retreat like no other. Soak in our luxurious hot tub, cool off in the cowboy pool, dark sky area for star gazing, hiking and explore the property in our Kawasaki Mule rental.

4.98 out of 5 average rating, 121 reviews

A spacious living area features a stylish design with two blue chairs and a light-patterned rug. Natural light fills the room through multiple windows. A modern fireplace with a decorative mantle adds warmth, while a dining area with orange chairs is visible in the background.

Cottage in Kerrville

Garrett House | Hill Country retreat Kerrville - p

The Garrett House is a Dwell Well vacation rental property located in the heart of Downtown Kerrville, TX. The Garrett house has many amenities like a well-appointed kitchen, POOL, HOT TUB, OUTDOOR SHOWER, FIRE PIT, and Herb Garden. This home is walking distance to many great restaurants, coffee, bars, theater, river trail and more. This property is ideal for entertaining and family vacations. This charming remodeled 100-year-old home is the perfect spot for your Texas Hill Country getaway!

4.98 out of 5 average rating, 268 reviews

A cozy bedroom features a queen size bed with a blue patterned quilt, complemented by matching pillows. A small bedside table holds a lamp, and a decorative mirror adorns the wall. A patterned rug covers the floor and a comfortable chair is positioned near the window.

Guesthouse in Kerrville

Adorable 3 room guest house w/ pool and amenities

Relax at this peaceful place. Pool, gated homestead in a comfortable hill country setting. Seven minutes from Interstate 10… 50 minutes to San Antonio 30 minutes to Fredericksburg. We have a twin size air mattress if needed. Enjoy the Texas Hill Country wineries, music, rivers, parks and shopping. Quaint decor, queen size bed, bath and kitchen on eleven acres. Owners are often around to assist and help. This is Not Self check in, we will be here to garage dog and open the gate. Ty!

The outdoor patio features a cowboy pool surrounded by greenery and a shade umbrella. Two hanging chairs provide seating, and a cozy blanket is draped over one. Strings of lights illuminate the space, enhancing the inviting atmosphere under the evening sky.

4.87 out of 5 average rating, 164 reviews

Hot Tub, Cowboy Pool, Pet Friendly, Country Views!

The Container Haus is contemporary and industrial design with many unique features, recessed lighting, modern designs and countertops throughout, high quality leather furniture and lots of windows and light complete this cozy and inviting abode. You can expect to experience a great deal of fun with our outdoor patio that includes a hot tub and cowboy pool. Enjoy being in the country with country views, but also enjoy being close to downtown just minutes away. Managed by Heavenly Hosts

4.97 out of 5 average rating, 163 reviews

Fredericksburg 3BR•Pool•Hot Tub• Wine Trail• Pets

Your Fredericksburg basecamp for wine country, bachelorette weekends, and family trips. Acorn Haus is a 3-bedroom modern farmhouse with three king suites, sleeping 8 with a private heated pool and hot tub, minutes from historic Main Street and the 290 wine trail. Boho-chic interiors, full kitchen, fast WiFi, free parking, and dog-friendly. Walk to tasting rooms and dinner, then come home to the pool. Every couple gets a king - nobody draws the short straw. Easy Instant Book.

4.9 out of 5 average rating, 337 reviews

A modern A-frame interior features a spacious living area with large windows offering views of surrounding greens. A dining table is set for four, while a light grey sofa invites relaxation. Natural wood accents enhance the atmosphere, complementing the design's rustic elegance.

Cabin in Fredericksburg

Hill Country A-Frame Cabin | Pool, Sauna & Nature

🌄 Modern A-Frame cabin on 17 scenic acres near Fredericksburg 🛏️ Sleeps up to 9 with 3 bedrooms + loft + sofa bed 🌿 Private patio with grill, fire pit & stock tank pool (heated option) 🧖 Access to shared cedar sauna on-site ☕ Fully equipped kitchen with local Hill Country coffee 🚗 Easy self check-in & on-site parking 💕 Family-friendly with loft hangout 🌌 Incredible stargazing in a Dark Sky Community 🦌 Peaceful Hill Country setting minutes from Main Street

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.

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

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.

An outdoor deck features a glimpse of a plunge pool surrounded by natural scenery. Two lounging chairs are positioned next to a small dining table. The sky displays soft pastel hues during sunset, enhancing the tranquil setting of the area.

5.0 out of 5 average rating, 315 reviews

Luxury+Privacy+Pool+Near Town

Escape the hustle to this Guest House located on 15 private acres just a 5 minute drive to town in an exclusive gated subdivision. You'll love the tranquil setting and privacy all while being a short drive to Main Street. We hope this will be a restful and restorative place for couples to enjoy quality time together in a romantic setting or for someone to enjoy a quiet retreat alone in a peaceful setting.

Popular amenities for Comfort rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.95 out of 5 average rating, 131 reviews

A serene pool area features shimmering turquoise water, complemented by streamlined steps leading to an adjacent hot tub. The expansive view offers rolling hills and open skies, framed by trees and a secure fence. Two white chairs are positioned nearby for relaxation.

Home in Bandera

Beautiful Lake View Home in Bandera

A central courtyard features a swimming pool outlined by a brick border. Surrounding the pool are modern lounge chairs and potted plants. Iconic cobalt blue doors are visible, leading to the interior space, while the area is shaded by mature trees.

4.97 out of 5 average rating, 180 reviews

SEVEN O ONE | Mid-Century Icon with Pool

4.9 out of 5 average rating, 146 reviews

Home in Kerrville

Hilltop BnB, Pool game-room view,Axis, near river!

4.97 out of 5 average rating, 200 reviews

Home in San Antonio

Casa Bella Hideaway Retreat with Pool

4.99 out of 5 average rating, 188 reviews

Home in Spring Branch

Relax and Enjoy the Views of the Hill Country

A covered outdoor living space features a combination of comfortable seating and a coffee table, surrounded by natural wooden walls. Ceiling fans are present to provide airflow. Soft lighting from string lights creates a welcoming ambiance, enhancing the area’s connection to the surrounding garden.

4.99 out of 5 average rating, 318 reviews

Near Main ~ Swimming Pool & Stunning Outdoor Area

4.94 out of 5 average rating, 103 reviews

Home in San Antonio

The Treehouse At La Cantera | 5 Min to Six Flags

4.98 out of 5 average rating, 369 reviews

Tejas Hills Guest Haus #2 | Hill Country + Pool

Condo rentals with a pool

A family-friendly pool area features a white waterslide entering a clear blue pool. Lush green landscaping with shrubs and tall cypress trees surrounds the pool, and a stone structure is visible in the background against a bright blue sky.

4.77 out of 5 average rating, 158 reviews

Hunt, TX 3 Bedroom Condo-Sleeps 10-Pools w/ Slides

A clear blue pool features a gentle water slide that cascades into the inviting water. Surrounding the pool are decorative stones and landscaped greenery, with tall conifer trees adding height and a sense of tranquility to the area.

4.91 out of 5 average rating, 11 reviews

Luxury 3 Bed Villa - Sleep 10 - Pools w Slides BBQ

The image features a modern stone building overlooking a tranquil pool at twilight. Soft lighting illuminates the structure, while a full moon casts a gentle glow over the water, enhancing the peaceful ambiance of the outdoors.

4.67 out of 5 average rating, 3 reviews

Stablewood, TX, Studio Presidential #1

A landscaped area features a large rock and a clay pot surrounded by green shrubs and agave plants. A colorful windmill fixture adds a touch of whimsy, with the backdrop of a two-story log building and trees under a partly cloudy sky.

Condo in Pipe Creek

Perennial VC Bandera 2A

The outdoor pool features a clear blue surface and is surrounded by a stone wall. A terrace with seating overlooks the water, while a rustic building is set in the background, complete with a tiled roof and lush green vines growing along the edge.

Worldmark Hunt- Stablewood Springs Resort 2BD

The entrance of Éilan Hotel & Spa is showcased, featuring a grand façade with Tuscan-inspired architecture. A series of elegant stairs lead to the main entrance, flanked by decorative lampposts and lush landscaping. A fountain can be seen in the foreground, enhancing the welcoming ambiance.

Condo in San Antonio

Éilan Hotel & Spa -San Antonio, TX- 1Bd Suite

The outdoor pool area features a serene swimming pool surrounded by palm trees and lounge chairs. Comfortable seating is arranged near the water, with a round table showcasing a decorative drink. The hotel’s elegant façade is visible in the background, reflecting a relaxed atmosphere.

Condo in San Antonio

Eilan Hotel and Spa

A large swimming pool is surrounded by a natural stone wall, reflecting the warm hues of the setting sun. Beyond the pool, a rustic building with a gabled roof can be seen, accented by greenery and outdoor seating areas.

4.7 out of 5 average rating, 90 reviews

WorldMark Hunt - Two Bedroom

Other vacation rentals with a pool

Farm stay in Fredericksburg

An aerial view of the ranch showcases a spacious outdoor area with a pool surrounded by a stone patio. A covered seating area and sunshade are visible nearby, along with well-maintained green lawns and the surrounding landscape of trees and open fields.

Stunning Fredericksburg Ranch House with POOL

4.95 out of 5 average rating, 332 reviews

4.98 out of 5 average rating, 124 reviews

A welcoming porch area features two comfortable chairs overlooking the scenic surroundings. The view includes a gravel path leading to a swimming pool, with greenery and trees creating a tranquil atmosphere. Natural light brightens the space, enhancing the relaxing outdoor setting.

Cottage in Kerrville

Madrona Hills #2 Pool, Hot tub and Gas fire pit

Farm stay in Fredericksburg

The modern barn retreat features a red exterior with large glass windows, showcasing an inviting design. A circular pool sits in the foreground, surrounded by green lounge chairs, inviting relaxation amid a spacious grass lawn.

Big Red Bunk Haus, 8 BR/ 4.5 BA, Sleeps 16

4.96 out of 5 average rating, 164 reviews

4.99 out of 5 average rating, 342 reviews

A serene outdoor setting features an inviting plunge pool with a rubber duck floating on the surface. Two Adirondack chairs are positioned nearby, illuminated by string lights overhead against a dusky sky. The landscape showcases trees and distant hills, creating a peaceful atmosphere.

Tiny home in Pipe Creek

Remote Tiny / Plunge Pool / Hiking / Breakfast

Townhouse in Fredericksburg

A private courtyard features a splash pool and a hot tub, with a vibrant orange umbrella providing shade. A gas grill is positioned nearby, while the surrounding walls create a quiet, enclosed space for relaxation.

3Bed/2Bath Pool Hottub Right off Main Street

4.91 out of 5 average rating, 142 reviews

5.0 out of 5 average rating, 4 reviews

An aerial view showcases a private plunge pool, surrounded by a wooden deck and lounge chairs. A circular fire pit sits in the center of a gravel area, flanked by seating arrangements. The iconic Airstream and multiple buildings are visible, with green grass surrounding the space.

Home in Comfort

House w/ Airstream | Cabin | Plunge Pool | Firepit

4.71 out of 5 average rating, 59 reviews

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

Hilltop Retreat