Holiday rentals with a pool in Kerrville

4.96 out of 5 average rating, 259 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.

4.97 out of 5 average rating, 99 reviews

Close to Main- In Ground Pool, Hot Tub, Game Room

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 out of 5 average rating, 241 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.

4.97 out of 5 average rating, 117 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!

4.94 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.

4.98 out of 5 average rating, 666 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.

4.98 out of 5 average rating, 258 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.

Guest house 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!

4.98 out of 5 average rating, 122 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

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, 140 reviews

3Bed/2Bath Pool Hottub Right off Main Street

This exquisite townhouse is right off Main St, within WALKING distance to the heart of Fredericksburg including shops, restaurants and wineries! Enjoy your own PRIVATE courtyard with a PRIVATE splash pool, gas grill, outdoor TV, and hot tub!! Come relax in the luxurious interiors with a fireplace and stylish decor. We are pet friendly! A small pet fee of $50 per pet. This newly built Fredericksburg Farm Modern Sunday Haus has keyless entry for easy contactless check in.

Treehouse in Fredericksburg

4.88 out of 5 average rating, 161 reviews

Mesquite Treehouse @ A-Frame Ranch

Escape to a modern A-frame treehouse just outside Fredericksburg. Nestled on 17 acres, The Mesquite Cabin offers Hill Country views, stargazing, and deer sightings, yet you’re minutes from Main St. Swim in the container pool, gather at the fire pit, or simply unwind on your private balcony. Inside, enjoy a king bed, rainfall shower, luxe linens, and modern amenities. The perfect blend of nature and comfort awaits.

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 out of 5 average rating, 304 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.

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.