Holiday 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.

FamilyLocationIndoor spaces

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

• Private couples getaway in the Texas Hill Country - Awarded Airbnb’s coveted top 5% of homes and “Guest Favorite”. • The beautiful view, plunge pool, and private hiking trails are what guests love the most about this secluded tiny home. The "Tiny" is perched on a hilltop (elevation 1800 feet!) overlooking some of the prettiest landscape in all of Texas and is a great choice for a romantic getaway or a quiet escape from the city. • Unique amenities: Private hiking trails & Plunge Pool for 2!

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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.

ValueLocationCheck-in

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, 244 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.

LocationValueIndoor spaces

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!

LocationFamilySleep quality

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!

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An outdoor gathering area is surrounded by towering oak trees, featuring a circular fire pit made of stone. Several comfortable chairs are arranged around the fire pit, creating an inviting space for socializing. A rustic structure with a grill is visible in the background.

4.96 out of 5 average rating, 101 reviews

Large Groups-Pool/Spa/Game Room/Guest House

**Luxury Retreat: Modern Farmhouse with Casita & Resort-Style Amenities** Escape to this Luxury farmhouse with a charming casita (full 1 bedroom apartment above game room), nestled among oak trees just outside of town. Enjoy the game room with twin bunks and twin rollaway cots, heated pool, fire pit, and spa house with jacuzzi. Perfect for family or friends—your serene getaway awaits! Book now! 6 Min Drive -Main Street 15 Min Drive- Grape Creek Vineyards 33 Min Drive- Enchanted Rock

LocationFamilyPool

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.

4.85 out of 5 average rating, 165 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

ValueLocationAccuracy

4.94 out of 5 average rating, 157 reviews

Farm in Fredericksburg

Grand Oaks Ranch · Pool·Spa · Game Barn · Animals

Built beginning in 1848 and over several generations, Grand Oaks Ranch is a historic limestone farmhouse sleeping 16 on 22 private Hill Country acre with a resort pool, hot tub, fire pit, and barn. Unwind poolside, sip wine at sunset, roast s'mores under the stars, or challenge your crew to a late-night ping pong battle in the barn. Friendly cows, goats, and horses roam the property. Minutes from Main Street and the wineries. Authentic Texas ranch life with every comfort you'd want.

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Cottage in Fredericksburg

4.99 out of 5 average rating, 147 reviews

Your Favorite! WALK to Main Pool/Hot Tub Sleep 6

This will be your favorite! Experience the charm of Fredericksburg Cottage, nestled in the heart of Fredericksburg. This curated 3-bed, 2 bath Craftsman style bungalow offers the perfect blend of vintage charm & modern amenities for your next getaway. The Cottage is walking distance to many of the finest dining establishments and 0.06 miles from Main Street with all its offerings. Book now to secure your stay today!

FamilyValueHiking

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, 320 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.

LocationValueCleanliness

A serene pool area features a clear blue swimming pool with a connected hot tub, surrounded by a natural landscape of trees. Two lounge chairs are positioned nearby, offering a space to relax and enjoy the views.

4.92 out of 5 average rating, 117 reviews

Private Home for 8 Stunning Pool

Welcome to Hendrix’s Hideout! This new build home offers a light and minimal design so that throughout your stay you can focus on taking in the beautiful Hill Country Views we are nestled in. Begin your day with a swim or end it by lounging pool side or maybe a round of corn hole. Either way we guarantee your favorite thing to do will be watching the sunset turn into a evening of star gazing.

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Popular amenities for Comfort rentals with a pool

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.96 out of 5 average rating, 165 reviews

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

FamilyValueTV

4.97 out of 5 average rating, 124 reviews

Home in Bulverde

Hill Country LUX | Pool & Horses

FamilyValueComfort

4.97 out of 5 average rating, 201 reviews

Home in San Antonio

Casa Bella Hideaway Retreat with Pool

LocationFamilyCondition

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

ValueLocationOutdoor spaces

4.94 out of 5 average rating, 107 reviews

Home in San Antonio

The Treehouse At La Cantera | 5 Min to Six Flags

ValueFamilyWi-Fi

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

FamilyLocationAccuracy

4.97 out of 5 average rating, 144 reviews

The kitchen features a spacious island with seating for four, surrounded by modern cabinetry. Stainless steel appliances, including a refrigerator and microwave, are visible. Soft lighting illuminates the countertops, which are equipped with various cooking essentials, creating an inviting atmosphere for meal preparation.

Home in San Antonio

Heated Pool Luxury Oasis 5 bed/2 master suites

FamilyValueTV

4.93 out of 5 average rating, 366 reviews

Das Bach Haus - Heated Pool, Hot Tub & Game Room

LocationFamilyBackyard

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

ValueLocationLayout

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

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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

LocationHospitality

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

ViewSleep qualityNearby

An expansive outdoor pool with a stone border is highlighted in the image. Lounge chairs are arranged around the pool area, providing a space for relaxation. Gentle landscaping and stonework add to the serene atmosphere of the resort, framed by trees and buildings in the background.

*Worldmark Hunt- Stablewood Springs Resort 1BD

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

Hospitality

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, 91 reviews

WorldMark Hunt - Two Bedroom

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Other holiday rentals with a pool

4.97 out of 5 average rating, 217 reviews

Guesthouse in Boerne

Hill Country Outdoor Retreat | Bluebonnet Oasis

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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.

4.96 out of 5 average rating, 165 reviews

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

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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.

4.95 out of 5 average rating, 333 reviews

Stunning Fredericksburg Ranch House with POOL

ValueFamilyIndoor spaces

5.0 out of 5 average rating, 5 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

LocationFamilyBathroom

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

ValueFamilyPool

4.95 out of 5 average rating, 56 reviews

A spacious dining area features a long wooden table surrounded by black chairs. Colorful glass vases of varying shapes and sizes are arranged on the table, drawing attention. Natural light floods through large windows, complemented by geometric wall art that accents the room's modern design.

Home in Comfort

Relaxation+Pool & Hot Tub+Views

FamilyLocationComfort

4.88 out of 5 average rating, 16 reviews

A natural stone pathway leads to a spacious outdoor area surrounded by lush green grass and shaded by mature trees. The screened-in porch and patio areas are visible, featuring dining sets and an outdoor grill, all set against a backdrop of the Texas Hill Country sky.

Farm in Comfort

Guest House @Riven Rock Ranch in Comfort TX

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