Vacation rentals with a pool in Gillespie County

A studio sleeping area is presented with a spacious bed featuring a white duvet and decorative pillows. Natural light filters through sheer blinds on three windows, illuminating the warm wooden floor. Two bedside lamps with textured bases are positioned on either side of the bed.

4.83 out of 5 average rating, 450 reviews

The Downtown Studio 3, Hot tub, Cowboy Pool!

Need to get away for a few days and enjoy some time in our quaint little town? Wine tasting maybe? Book this recently remodeled studio, just 2 blocks from the heart of it all and wake up, enjoy a cup of coffee from the Keurig coffee maker and go exploring! Afterwards come back and relax in your own private hot tub. Did we mention the location? This studio is in our beloved historic district just steps to all the festivals and festivities Fredericksburg is known for. Managed by Heavenly Hosts

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, 148 reviews

*NEW* MODERN HAUS Pool Courtyrd & Firepit Off Main

The HAUS on Washington is a completely renovated 7 bedroom, 5 bathroom sprawling compound near Main that is perfect for girls' trips, couples getaways, and family gatherings! This house boasts a luxury, modern feel with spacious indoor and outdoor living areas with resort style pool & spa. House sleeps 14 in 7 beautiful bedrooms with all king and queen beds. Additionally, with 4 living rooms, big dining room, and a vintage sunroom, you will love relaxing here! We look forward to hosting you!

4.92 out of 5 average rating, 116 reviews

Ranch in Fredericksburg

Rustic Soul, Modern Comfort | Relax on the Ranch

Step back in time, with the modern comforts you love, at Grand Oaks Ranch, an 1848 homestead turned spacious 5-bedroom, 3-bath retreat on 22 peaceful acres. Unwind by the pool, sip wine at sunset, roast s’mores in the fire pit, or take on your friends in a late-night ping pong battle. Just minutes from Main Street and wineries, this authentic ranch offers rustic charm, wide-open views & friendly cows, goats, and horses. Whether heading out or staying in, it’s the perfect Hill Country escape.

4.94 out of 5 average rating, 148 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 structure with a tent-like top is surrounded by trees. The design features large, glass walls and a wraparound deck with stairs leading up. A circular gravel area with a metal fire pit and lounge chairs enhances the outdoor space.

Yurt in Fredericksburg

4.89 out of 5 average rating, 142 reviews

Ultra Lux Landscape Tree House resort. Pool! Tub!

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, 286 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 serene pool area featuring a clear blue swimming pool with a spa section. Surrounding greenery and lounge chairs offer a peaceful retreat. A covered outdoor seating area can be seen in the background, accompanied by a red umbrella providing shade.

4.97 out of 5 average rating, 199 reviews

Luxe Historic Estate-Pool & Hot Tub-Walk to Main!

History meets Luxury at Sweet Escape! * Restored Historic 4 bedroom/3 bath for up to 13 guests on a 2/3 acre Estate. * Outdoor entertaining with grill, fire pit, corn hole, swimming pool and hot tub! (Heated pool option) * Gourmet kitchen * Indoor Pool table, record player, and games! * 1 block off W. Main Street (& 6 blocks to Marketplatz). I delight in helping you Elevate your trip! Tell me what type of group you are bringing and I will help you put together a memorable stay!

4.98 out of 5 average rating, 158 reviews

The Farmhouse: Modern Retreat in Fredericksburg

Welcome to The Farmhouse, a modernized 1930’s craftsman home on a family-owned homestead in Fredericksburg, Tx. - Private guesthouse with expansive outdoor entertainment area - Master bedroom with king bed, private bathroom, and Roku TV - Additional bedrooms with king beds and shared bathroom - Full kitchen and dining for 10 - Freeform swimming pool with grotto waterfall - Outdoor kitchen with gas grill and dining space - Complimentary Wifi access

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, 218 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 ☀️

Treehouse in Fredericksburg

4.95 out of 5 average rating, 131 reviews

Pecan Treehouse @ A-Frame Ranch

Escape to a modern A-frame treehouse just outside Fredericksburg. Nestled on 17 acres, the Pecan 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, dual rainfall shower, luxe linens, and modern amenities. The perfect blend of nature and comfort awaits.

4.94 out of 5 average rating, 290 reviews

The Birdhouse - Hot Tub, Pool & Fire Pit!

The Birdhouse is a newly renovated house located less than half a mile from Main St. Our home features 2 bedrooms, 1 bath, a make-up area, a private backyard with a patio, a fire pit, a brand new hot tub and a cowboy pool! The home has one king and two queen beds and a very comfortable couch. It also features a TV, high speed WiFi, a washer / dryer and a full kitchen with brand new appliances!

A serene outdoor setting features a sparkling pool framed by elegant lounge chairs with striped cushions. Views of rolling hills and trees stretch into the distance under a bright blue sky with scattered clouds. A covered patio with dining space is visible in the background.