Vacation rentals with a pool in Gillespie County

4.94 out of 5 average rating, 144 reviews

A refreshing swimming pool is set within a spacious stone patio, surrounded by lush greenery and vibrant flower pots. Lounge chairs are positioned nearby, offering an inviting space to relax. A scenic view of the expansive Hill Country landscape is visible under a backdrop of partly cloudy skies.

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.

Treehouse in Fredericksburg

An A-frame cabin is elevated on wooden stilts, featuring a striking triangular roof. Large windows allow natural light to illuminate the interior, while a spiral staircase leads to an upper deck. Surrounding native post oak trees add to the rustic charm of the structure.

4.95 out of 5 average rating, 113 reviews

Pecan Treehouse @ A-Frame Ranch

The Pecan Cabin at A-Frame Ranch is a modern A-frame treehouse set on 17 beautiful acres right on the edge of charming Fredericksburg, TX. This is a place to truly unwind and feel like you’re out in the country, while being less than a 10 minute drive to Main Street. The area has so much to offer, from dance halls and wineries, to gourmet restaurants and hiking. Or stay in the entire weekend- sit back on your private balcony while gazing at the stars or watch the deer go by in the morning!

Superhost

A modern treehouse structure is perched among the trees, featuring distinctive angular architecture and wooden siding. Windows are positioned to provide views of the surrounding forest. A pathway leads from the ground to a wooden deck that connects to the treehouse.

Treehouse in Fredericksburg

4.89 out of 5 average rating, 223 reviews

Luxury Tree House X Magical Romantic Forest! Pool!

Imagine being immersed in a small enchanted forest only 100’s of feet off of Main street. Nestled into live oak trees that gently sway in the breeze, under dark skies with bright stars, and curated to both inspire joy and create presence. Welcome to our little magical treehouse and landscape resort in Fredericksburg. The amazing stays in our secluded forest are only minutes to all of the beautiful shops, cafes, restaurants, bars, and Vineyards. A magical stay that we hope you will love.

A light-colored exterior of the house is shown, with a wooden deck featuring several lounge chairs adorned with colorful cushions. A private swimming pool reflects the sunlight, creating a serene outdoor space complemented by landscaped greenery.

4.99 out of 5 average rating, 275 reviews

Near Main ~ Swimming Pool & Stunning Outdoor Area

The Travis House is a gorgeous 1960's ranch style home that has been totally transformed and updated into a beautiful bright and airy home! With a BRAND NEW PRIVATE SWIMMING POOL AND HOT TUB and located just 3 blocks from Main Street on the west end of town, you will not find a more perfect location for your large group! The Travis House is made up of 4 bedrooms, 2 baths and 2 living areas, & a makeup area to get ready! Only one mile to Hondo's Crossroads & Altdorfs. Permit #8056001175

A spacious outdoor area features a uniquely shaped pool, complete with a cascading spa and surrounding stonework. The main house, with a modern metal roof, showcases large windows that invite natural light. A windmill stands nearby, adding to the rustic landscape.

5 out of 5 average rating, 17 reviews

Adobe Creek Ranch - Pool, Hot Tub & Fire Pit

Gather your group and escape to Adobe Creek Ranch, a Texas Hill Country haven near Fredericksburg! Nestled on 25 private acres, this retreat offers the best of ranch life with all the luxuries of a boutique rental. With the Main House, Cowgirl Cabin, and Barn House, it comfortably sleeps up to 14 guests. Dive into the private pool, soak in the hot tub, sit by the fire pit, walk private paths, and take in breathtaking vistas. Adobe Creek Ranch is ready to make your stay unforgettable.

Superhost

An outdoor patio area is presented, featuring a hot tub, cowboy pool, and a cozy fire pit surrounded by comfortable seating. Soft lighting enhances the space, bordered by lush greenery, with the entrance to the house visible in the background.

4.88 out of 5 average rating, 129 reviews

Container Haus, Hot Tub, Cowboy Pool, Pet Friendly

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

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.

4.9 out of 5 average rating, 105 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.

Place to stay in Fredericksburg

An exterior view of the uniquely designed silo features a circular structure with a turquoise door, surrounded by lush green grass. A paved walkway leads to a fire pit area with black chairs and a heated cowboy pool, enclosed by a wooden fence.

4.99 out of 5 average rating, 433 reviews

The Silo: Modern design, private, *heated pool*

Less than 3 miles from Main Street, The Silo rests on 40 acres in the wide open space of the Hill Country providing a unique get-away. Enjoy a breath-taking sunset as you stroll down the private granite road frequented by native wildlife and blackbucks, before heading to downtown Fredericskburg for fine dining, local wines, and one-of-a-kind shopping. We want your stay to be wonderful and are happy to share local recommendations for an authentic experience.

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, 200 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. Follow us @revivalridge on IG ☀️

4.93 out of 5 average rating, 108 reviews

Ranch in Fredericksburg

Pool/Spa, Fire Pit, Game Barn, Friendly Animals!

Step back in time with modern comforts at Grand Oaks Ranch—an 1848 homestead turned spacious 5-bedroom, 3-bath retreat on 22 peaceful acres. Just minutes from Fredericksburg’s Main Street and wineries, this authentic ranch offers rustic charm, wide-open views, and friendly resident cows, goats, horses and more. Whether you’re exploring the area or staying in, it’s the perfect Hill Country escape.

Farm stay in Fredericksburg

A circular pool is pictured in the foreground, featuring clear blue water. Beyond the pool, expansive grassy fields are visible, dotted with a few trees. The clear blue sky provides a bright backdrop, enhancing the tranquil outdoor setting.

4.97 out of 5 average rating, 146 reviews

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

Experience the perfect relaxation & getaway in our modern retreat featuring 8 bedrooms and 4.5 bathrooms across 3,500 sq. ft. private estate. Conveniently located a stone's throw from local wineries, shopping destinations, museums, and nature trails, it’s the perfect place for families, a girls' getaway, reunions and even corporate team buildings. Everyone is welcome!

Farm stay in Fredericksburg

The outdoor pool features a spacious design with smooth stone edges and a hot tub integrated beside it. The vibrant blue water contrasts with the grassy surroundings, while a colorful sunset paints the sky in hues of orange and purple.

4.95 out of 5 average rating, 289 reviews

Stunning Fredericksburg Ranch House with POOL

Guests love staying here at Rose Ranch because of the proximity to many wineries, Alstadt Brewery, the amazing views, peacefulness of the ranch, the hot tub drinking your favorite beverage and the night skies for star gazing, wild animals roaming by, our sweet donkeys and horses, and the big beautiful front porch to dream and sip coffee in the morning!

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Apartments

Convenient locations with everyday essentials

Cottages

Quaint homes, peaceful surroundings

Popular amenities for Gillespie County rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

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.

4.91 out of 5 average rating, 128 reviews

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

CourtneyRating, 5 stars1 month ago

Perfect setup for our bachelorette! There were fresh cookies waiting upon our arrival which was was so sweet. Host was easy to communicate with and check out was a breeze. Great experience!

A spacious living room features a large sectional sofa in a soft blue hue, complemented by two accent chairs. Sunlight floods through multiple windows adorned with natural shades, highlighting the warm wood accents on the ceiling. A simple coffee table rests atop a textured area rug.

5 out of 5 average rating, 27 reviews

3BR Scenic Setting w/ New Pool, 5 Mins to Main St!

KellyRating, 5 stars1 month ago

Great place to stay! Plenty of room and we felt right at home. Great hosts, very responsive, and great recommendations.

A spacious outdoor area features a covered porch supported by wooden beams. Picnic tables and brightly colored chairs are arranged around a grill, creating an inviting space for gatherings. The surrounding landscape includes greenery in the distance, contributing to a relaxing environment.

4.85 out of 5 average rating, 13 reviews

Luckenbach/ POOL/Hot Tub/ Sleeps 7

SandyRating, 5 stars6 months ago

The house was beautiful and very spacious for our small family Christmas celebration. We had everything we needed. Dawn was very helpful and quick to respond. We are planning on going again in the summer.

The exterior features a modern design with three converted shipping containers, highlighting blue and wooden siding. An upper deck is accessible via outdoor stairs, and a spacious outdoor area is visible, framed by trees under a clear blue sky.

4.92 out of 5 average rating, 39 reviews

Texas Wine Hill Country Private 12 Acre Experience

KristinaRating, 5 stars2 weeks ago

Had a wonderful time here! Quiet, secluded, beautiful. I like to explore, so there was a lot to explore. Had 4 friends, and we all enjoyed our sleeping areas! A tip to know if you’re gonna cook, the stoves are not the most effective for massive meals. But we made do and it wasn’t a issue! (Definitely use the grill) Our host was fantastic and kept us updated throughout the trip including a later check out time, which we all enjoyed so much. Thank you for allowing us to stay and relax for the weekend!

A modern home with a sloped roof is set against a bright sky, featuring an inviting swimming pool surrounded by lounge chairs. An outdoor dining area is shaded by large umbrellas, with a hot tub nearby. Lush greenery surrounds the property.

4.97 out of 5 average rating, 88 reviews

Beautiful Home, Pool, Hot Tub & Pet Friendly!

SuzannaRating, 5 stars1 week ago

This stay completely exceeded my expectations! The property was even better than the pictures – clean, beautifully maintained, and filled with thoughtful touches that made it feel special. The highlight for me was definitely the pool and hot tub. Both were spotless, well-maintained, and created the perfect setting to relax and unwind. The host was outstanding – friendly, responsive, and made sure everything was perfect from check-in to check-out. The space was cozy, the bed was super comfortable, and everything I needed was right at my fingertips. If you’re looking for a peaceful and luxurious getaway with the added bonus of your own private pool and hot tub, this is the place. I would stay here again in a heartbeat! Thank you for such an unforgettable stay!

A heated pool with a submerged edge is surrounded by a wooden deck and lounge chairs. A landscaped yard features green grass and a patio area with dining furniture, along with a barbecue grill and palm tree providing a tropical touch.

4.93 out of 5 average rating, 68 reviews

Heated Pool | Hot Tub | 3 min to Main

ZeeRating, 5 stars2 months ago

We had a great friend's reunion! The house was very clean and full of amenities. We loved used the fire pit and pool/hot tub every night. The backyard was peaceful and clean. We had coffee at both the outdoor and indoor tables. Wonderful experience.

A large in-ground pool reflects the surrounding mature trees and patio area. A covered seating area is visible, along with a grassy lawn and lounge chairs. The backyard offers a tranquil space for relaxation and outdoor activities.

4.93 out of 5 average rating, 27 reviews

Fall Sale! Pool | Pets | Firepit | Games | Quiet

MalloryRating, 5 stars1 week ago

My family and I loved staying here, and would definitely stay again! From the privacy fenced backyard (perfect for our dog), to the pool which my kids swim in every day, to the perfect location to Main St. and Enchanted Rock, to the cleanliness and fast response time of Lauren and Matt, it was a 10 out of 10 stay. We can't wait to come back!