Holiday rentals with a pool in Kerrville

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.

FamilyValueOutdoor spaces

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.

LocationFamilyAmenities

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.

ValueFamilyNearby

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!

LocationFamilyAmenities

4.99 out of 5 average rating, 677 reviews

A wooden cabin with a screened porch sits amidst a spacious outdoor area. Colorful lounge chairs and a stone fire pit surround the cabin, while an inflatable pool and a shaded seating area with umbrellas are visible. Lush greenery provides a natural backdrop.

Cabin in Harper

Hill Country Cabin

Hill Country Cabin 5 fenced acres pets welcome. When bringing a pet not well behaved please let me know in advance all good. Relax in the Hot Tub or cool off in the 8 foot filtered galvanized pool. Enjoy the fire pit sun sets and star gazing. There's a deck or screened porch where you can enjoy your morning and watch nature waking. There is a fridge, gas griddle, charcoal grill, electric griddle, microwave, portable oven 2 burner hot plate. Along with everything you'll need to cook with.

ValueLocationAccuracy

4.94 out of 5 average rating, 156 reviews

A cozy living area features a large stone fireplace, wooden floors, and a mix of rustic décor. A comfortable couch is positioned beside a dining table, while a spiral staircase leads to the loft area. Natural light is provided by the windows adorned with decorative glass.

Cabin in Fredericksburg

The 1851 Cabin at Wolf Creek Guest Ranch

The Wolf Creek Guest Ranch is the perfect place to experience an original log cabin on a private working horse ranch. The cabin was originally built in Arkansas in 1851, carefully taken down and rebuilt into a very comfortable rental. Guests will find this beautiful cabin equipped with air conditioning, heat, a soaking tub, and a huge stone fireplace to enjoy on those winter nights after a day of wine tours, shopping, restaurants and outdoor activities that Fredericksburg has to offer.

ValueFamilyGetting around

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!

FamilyValueAir conditioning

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

ValueFamilyView

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

Our one bedroom cottage in the majestic hills of Kerrville is the perfect place for a short getaway or a working vacation (fiber internet on property). Enjoy the amazing sunsets from your porch, take a dip in the pool, and pass the afternoon in our outdoor area with pergola, lounge chairs, and grills. In the country, just 8 minutes from Kerrville, Louise Hays River Park (kayaking, paddle boarding), H.E.B. grocery store, and great dining and entertainment options. NO PETS ALLOWED

LocationFamilyDecor

4.97 out of 5 average rating, 164 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.

FamilyValueOutdoor spaces

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, 317 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.

LocationFamilyKitchen

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.

ValueFamilyOutdoor spaces

Popular amenities for Kerrville rentals with a pool

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

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

ValueFamilyView

4.97 out of 5 average rating, 191 reviews

The Farmhouse: Modern Retreat in Fredericksburg

ValueFamilyCheckout

A modern open-concept living area features a cozy seating arrangement with two white armchairs and a large round coffee table. A stylish kitchen is visible in the background, equipped with sleek appliances and bar seating. Natural light illuminates the space through large windows.

4.92 out of 5 average rating, 101 reviews

Chastain Haus: Pool and Hot tub with all king beds

LocationFamilyCleanliness

A charming cottage, painted in soft yellow, features dark green shutters and an inviting porch. Rocking chairs are positioned on the covered entry, surrounded by lush greenery. A white picket fence encloses the front yard, enhancing the home's welcoming exterior.

4.96 out of 5 average rating, 176 reviews

3B/2B Pool & Hot Tub- 1 BLK to Main!

LocationFamilyQuiet

4.98 out of 5 average rating, 369 reviews

Tejas Hills Guest Haus #2 | Hill Country + Pool

LocationValueNearby

A split-image showcases a cozy living area with a large television mounted on a dark feature wall and a warm seating arrangement. The outdoor space features a heated swim spa and comfortable patio seating surrounded by a well-maintained yard and landscaped stones.

4.92 out of 5 average rating, 117 reviews

Close to Main, Heated Pool, Firepit, 220EV outlet!

LocationFamilyBarbecue

A glam suite features a vibrant pink lipstick-themed wall decorated with repeated lip prints. Three vanity spaces are positioned against the wall, illuminated by lighted mirrors. Soft pink stools are placed in front of the vanities, creating a cheerful and inviting area for preparation and pampering.

4.88 out of 5 average rating, 112 reviews

Pink Glam House

FamilyValueComfort

4.97 out of 5 average rating, 220 reviews

Upscale|Swimspa-pool|sauna|hot tub|2 blk to Main

FamilyLocationHospitality

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

FamilyValueBathroom

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

LocationFamilyComfort

A serene outdoor area is illuminated under a moonlit sky. The natural stone structure features large windows and is surrounded by a tranquil pool reflecting the night’s glow, adorned with neatly arranged potted plants along the edge.

5.0 out of 5 average rating, 16 reviews

Stablewood, TX, 1 Bedroom SN #1

LocationFamilyIndoor spaces

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

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 Flag 2A

NearbyViewSleep quality

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

LocationFamilyView

An entrance features natural stone arches and wooden doors, leading to a paved pathway. Rocking chairs provide seating on one side, while the surrounding greenery and distant views enhance the inviting atmosphere.

4.63 out of 5 average rating, 19 reviews

Stablewood Springs Resort

FamilyLocationNearby

Aerial view of the resort's expansive outdoor pool area is seen, featuring a large central pool with a surrounding deck. Multiple lounge chairs are arranged, and a separate hot tub can be observed. The resort's main building and landscaped grounds are visible in the background.

Modern Charm Condo For Kiddos Camp Drop Off!

ValueHospitalityAmenities

Other holiday 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.

4.95 out of 5 average rating, 333 reviews

Stunning Fredericksburg Ranch House with POOL

FamilyValuePool

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.

4.91 out of 5 average rating, 142 reviews

3Bed/2Bath Pool Hottub Right off Main Street

LocationValueAccuracy

Guesthouse in Fredericksburg

A private outdoor area features a hot tub and a swimming pool with glistening water, surrounded by a spacious patio. Natural light accentuates the wood-paneled wall and the glass doors leading to the interior, creating a serene atmosphere within a fenced backyard.

4.98 out of 5 average rating, 225 reviews

The Guest House on Elm

ValueFamilyView

4.97 out of 5 average rating, 216 reviews

Guesthouse in Boerne

Hill Country Outdoor Retreat | Bluebonnet Oasis

ValueLocationIndoor spaces

4.99 out of 5 average rating, 89 reviews

Cottage in Kerrville

Cosy Cottage-large yard w/lovely creek, fire pit

ValueFamilyView

5.0 out of 5 average rating, 8 reviews

Home in Bandera

T Mountain Ranch | Hilltop Luxury

FamilyLocationHot tub

Farm stay in Center Point

A spacious single-story house is situated on a well-manicured lawn, surrounded by natural landscaping. The home features a stone accent exterior and a covered porch. Blue skies with fluffy clouds create a serene backdrop, complementing the lush greenery of the property.

5.0 out of 5 average rating, 29 reviews

Spanish Oak Ranch

FamilyLocationAccuracy