Holiday rentals with a pool in Kerrville

4.96 out of 5 average rating, 262 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.

ValueFamilyHospitality

4.99 out of 5 average rating, 100 reviews

The Ranch House

The Ranch House is the perfect getaway for your family & friend gatherings & able to sleep up to 12 people with 4 bedrooms & 2 bathrooms. The open living room, dining room, & full kitchen offer plenty of space to visit, cook, & enjoy each other's company. The full front & back porches are lovely for hanging out. The back porch is screened in with a ping pong table. The large patio between the back porch & pool is the ideal place to BBQ, play cornhole, relax on the hammocks, & take in the views.

FamilyLocationAccuracy

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, 245 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.

LocationFamilyCondition

4.98 out of 5 average rating, 122 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!

LocationValueTV

4.99 out of 5 average rating, 681 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.

LocationValuePool

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!

FamilyValueHot tub

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, 103 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

LocationFamilyAir 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

ValueLocationLaundry

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

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Cottage in Fredericksburg

WALK to Main Street/Restaurants/Shops Pool/Hot Tub

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!

ValueFamilyParking

4.99 out of 5 average rating, 147 reviews

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, 323 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.

FamilyValueAccess

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, 119 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.

ValueFamilyGetting around

Popular amenities for Kerrville rentals with a pool

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.98 out of 5 average rating, 372 reviews

Tejas Hills Guest Haus #2 | Hill Country + Pool

LocationFamilyTV

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

FamilyLocationCleanliness

A collage of The Birdhouse showcases the inviting outdoor space featuring a wooden deck with a cowboy pool and a hot tub. Inside, a modern kitchen with wooden shelving and a spacious sleeping area with a patterned duvet cover and natural light highlights the home's comfort.

4.96 out of 5 average rating, 345 reviews

The Birdhouse - Hot Tub, Pool & Fire Pit!

ValueLocationBathroom

A refreshing pool surrounded by a stone deck features lounge chairs and vibrant greenery. Large oak trees provide shade, while a wooden fence adds privacy. Colorful planters with flowers enhance the outdoor space, creating an inviting atmosphere for relaxation.

4.92 out of 5 average rating, 149 reviews

Pool, Hot tub, Sleeps 10, Fire pit, Near Main St

ValueLocationHospitality

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, 178 reviews

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

LocationFamilyComfort

4.97 out of 5 average rating, 221 reviews

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

LocationFamilyOutdoor spaces

4.97 out of 5 average rating, 191 reviews

The Farmhouse: Modern Retreat in Fredericksburg

ValueLocationCheck-in

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, 319 reviews

Near Main ~ Swimming Pool & Stunning Outdoor Area

ValueLocationPool

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

ValueFamilyComfort

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

LocationFamilyView

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

FamilyLocationIndoor 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 Bandera 2A

NearbySleep qualityView

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.

4.71 out of 5 average rating, 92 reviews

WorldMark Hunt - Two Bedroom

LocationFamilyAmenities

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

FamilyLocationCondition

A bright living area is highlighted by a high ceiling with wooden beams. A comfortable leather sofa faces a wooden coffee table, while a patterned area rug adds warmth. Large glass doors invite natural light and provide views, complemented by a stylish light fixture overhead.

Condo in Ingram

1BR Condo in Stablewood Springs

Other holiday rentals with a pool

4.99 out of 5 average rating, 89 reviews

Cottage in Kerrville

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

ValueFamilyRiver

5.0 out of 5 average rating, 8 reviews

Home in Bandera

T Mountain Ranch | Hilltop Luxury

LocationFamilyHospitality

5.0 out of 5 average rating, 10 reviews

A spacious deck is furnished with two wicker chairs facing a view of surrounding trees and the landscape. A small wooden table holds a potted plant, creating a serene outdoor area for relaxation and enjoying the natural scenery.

Home in Ingram

Lodge II | Lake Views | Hot Tub | Pool + River Acc

FamilyAmenitiesAccuracy

5.0 out of 5 average rating, 19 reviews

The outdoor area features a tranquil pool surrounded by a natural stone patio. Comfortable seating arrangements are visible, with lush greenery and distant hills providing a serene backdrop under a clear blue sky.

Home in Bandera

Views! Pool, Hot Tub, Fishing Pond, Sleeps 17!

LocationValueIndoor spaces

5.0 out of 5 average rating, 6 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

FamilyLocationComfort

4.86 out of 5 average rating, 14 reviews

A serene pool area is visible, featuring clear blue water surrounded by natural stone landscaping. An umbrella provides shade over a lounge chair, while a fence encloses the space. Lush green trees and soft grass are seen in the background, enhancing the peaceful outdoor setting.

Home in Kerrville

Wine Country Oasis (POOL/SPA)

ValueFamilyTV

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.

Spanish Oak Ranch

LocationFamilyParks

5.0 out of 5 average rating, 30 reviews