Vacation rentals with a pool in Gillespie County

The exterior of a renovated farmhouse showcases a combination of classic and modern design elements. Large windows frame the entrance, while a teal door provides a pop of color. A well-maintained lawn surrounds the home, contributing to its inviting appearance.

4.95 out of 5 average rating, 272 reviews

Josies Farmhaus Stock Pool Hot Tub Wildlife

Josie's Farmhaus is a unique 1920's Farmhouse newly renovated for modern comfort and entertainment. Sleeping 10, this home is the perfect place for your group to call home while visiting Fredericksburg! Our 4-bed, 2-bath vacation rental is only a 1/2 mile south of Main St. and provides all the modern necessities to enjoy your stay! Visit our recommended wineries & enjoy all of the restaurants & shopping Fredericksburg has to offer. Come evening, wind down in the hot tub on our beautiful deck!

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.

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, 274 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

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, 128 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

Superhost

The A-frame cabin is nestled among native post oak trees, featuring a spacious deck with string lights. A firepit is positioned on the deck, alongside a stock tank pool. Large windows reflect the interior lighting, creating a warm atmosphere in the wooded surroundings.

Cabin in Fredericksburg

4.92 out of 5 average rating, 416 reviews

Modern A-Frame Cabin in Nature, Minutes from Main

The Comal Cabin at A-Frame Ranch is a modern A-frame cabin 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- relax on the deck while gazing at the stars and then watch the deer go by in the morning!

A modern building is presented with a spacious covered porch supported by sturdy columns. Dark railing surrounds the porch, where a set of chairs is visible. The structure is surrounded by natural landscaping, featuring trees and a gravel pathway leading to the entrance.

4.96 out of 5 average rating, 75 reviews

Oak Casita in The Glades

Welcome to Oak Haus in The Glades on winery corridor. Take it easy at this unique and tranquil getaway. Enjoy wine at the fire pit or coffee on the porch, where deer might scamper by. Spend your time relaxing, playing games or swimming in the heated cowboy pool (which is a 10 foot stock tank) in the common leisure corral. Visit the 12 wineries, brewery or two distilleries that are within one and a half miles of Oak Haus. Fredericksburg is just a short drive away.

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, 431 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, 197 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 ☀️

4.95 out of 5 average rating, 118 reviews

A modern kitchen features white cabinetry and granite countertops, complemented by stainless steel appliances. Pendant lights illuminate the space, while a ceiling fan adds ventilation. A dining area with black chairs is visible in the foreground, enhancing the functional layout of the room.

Loft in Fredericksburg

Moscato Cottage

Located in the heart of Texas Hill Country! The Moscato Cottage is an elegant 3,000 square foot private loft that includes 3 bedrooms and 2 bathrooms. Beautiful granite countertops, stainless steel appliances, hardwood floors, private patio and outdoor firepit, and brand new amenities... It is sure to blow you away! The Moscato Cottage is a loft located above the office at the Vineyards of Fredericksburg RV Resort.

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.

A contemporary living room features a wooden ceiling and concrete flooring. Comfortable armchairs face a wall-mounted television, while a cozy sofa is positioned nearby. Neutral decor and a decorative plant enhance the space. A modern fireplace adds character without being operational.

4.92 out of 5 average rating, 103 reviews

Schubert Haus - 2 BLKS to Main St, Hot Tub & Pool

Welcome to Schubert Haus! - Perfect for families, groups, and wine enthusiasts, our newly renovated home, located just two blocks from Main Street in Fredericksburg, offers three spacious bedrooms, two stylish bathrooms, and a beautiful backyard with a hot tub and cowboy pool. This is your ideal retreat for a memorable vacation. Book now for a perfect stay!

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Popular amenities for Gillespie County rentals with a pool

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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, 127 reviews

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

CourtneyRating, 5 stars3 weeks 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 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.

4.83 out of 5 average rating, 12 reviews

Luckenbach/ POOL/Hot Tub/ Sleeps 7

SandyRating, 5 stars5 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.

5 out of 5 average rating, 15 reviews

ThistleOaks Hillside Escape with Pool & Wildlife

AndreaRating, 5 stars2 weeks ago

This home was stunning! The house was HUGE. Our large group fit very comfortably. The pool was great and the lot itself was beautiful and very relaxing. We enjoyed being in nature and seeing the wildlife, but it was also very close to town. Pictures do not do it justice! We had everything we needed to cook and felt right at home. We will definitely try staying again!

The outdoor area is highlighted by a spacious in-ground pool, accompanied by a integrated hot tub. Lounge chairs are arranged nearby, and vibrant landscaping adds color. The covered porch features a stylish dining area, while an expansive lawn offers ample space for outdoor activities.

5 out of 5 average rating, 18 reviews

Sunshine Haus-5/3, Slps 14, LARGE HOT TUB & Pool

DanielleRating, 5 stars2 weeks ago

We had a great time! Plenty of space and the beds were comfortable. We loved the pool.

A spacious outdoor area features a resort-style swimming pool and spa, surrounded by neatly trimmed grass. A gazebo with seating is visible nearby, along with stone pathways that lead towards the pool area.

4.93 out of 5 average rating, 142 reviews

*NEW* MODERN HAUS Pool Courtyrd & Firepit Off Main

ElyseRating, 5 stars2 weeks ago

This is the 3rd time our group has rented this house, and we'd do it again and again. Not only is the house big enough for a group, it's absolutely stunning. It's decorated beautifully, the beds are comfortable, the yard is pristine. It's spread out enough that you can have people in the pool, people playing cornhole on the lawn, people reading on the patio, and people napping, all peacefully separated. But you can also all congregate to grill out for dinner. It's a dream. This year, the A/C went out on Sunday of a holiday weekend, and Rachel's team was somehow able to get someone over within an hour of us reaching out (on a SUNDAY on a HOLIDAY) to get it fixed ASAP. Such impressive customer service. We're always grateful for Rachel's hospitality and we cannot recommend staying here enough!

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 stars5 days 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!

An aerial view showcases a sprawling ranch-style home set on a green landscape. A large private swimming pool is flanked by lounge chairs, and the outdoor space includes a well-lit patio area. The serene countryside provides a peaceful backdrop at dusk.

4.9 out of 5 average rating, 73 reviews

Relaxing 5-acre Retreat | Guest House | Game Room

ElbenRating, 5 stars3 weeks ago

Beautiful and comfortable home with beautiful surroundings. The kids enjoyed the pool! (Note that one end is very deep). The kitchen was well stocked with equipment, and rooms were well furnished.

A modern rectangular heated pool is surrounded by a spacious patio and lounge seating. A shaded area features an outdoor dining arrangement, while large trees provide natural greenery. The pool reflects soft sunlight, creating a tranquil atmosphere ideal for relaxation.