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, 278 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!

A cowboy pool made of galvanized steel sits in a private outdoor area, surrounded by wooden fencing. Inflatable pool toys are placed in the water. Nearby, seating arrangements include a wicker chair with a striped cushion and a colorful potted plant adds a touch of greenery.

4.97 out of 5 average rating, 144 reviews

Claret House, Hot Tub, Cowboy Pool, Fire pit!

Claret House is a modern 1 bedroom home with an eclectic, artistic flair! This spacious yet cozy home has everything you need to relax and reconnect, even a small office if you need to do some work while you're away! Enjoy the hot tub or cowboy pool and soak any stress away! If you want to stay in and leave the hectic world behind, you can make a delicious meal in the fully equipped, large kitchen. And at the end of the day, rest well in the luxurious king-size bed! Managed by Heavenly Hosts

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 sleeping area features a spacious bed adorned with a textured blanket. Large glass doors open to a private deck surrounded by lush greenery. Comfortable seating is placed nearby, allowing for relaxation and enjoyment of the serene forest view.

Treehouse in Fredericksburg

4.89 out of 5 average rating, 195 reviews

Enchanted Tree House! Pool - Tub - Off Main St.

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, 285 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 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, 147 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 can't wait to host you!!

A freeform swimming pool is featured, complemented by a grotto waterfall cascading over natural stone. Adjacent to the pool, a hot tub provides a relaxing space, surrounded by greenery, creating an inviting outdoor setting.

4.98 out of 5 average rating, 157 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, 215 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 ☀️

Townhouse in Fredericksburg

A private splash pool is surrounded by a spacious outdoor area featuring a seating arrangement and an umbrella for shade. The townhouse exterior showcases a striking red brick facade and multiple balconies, contributing to the inviting atmosphere of the courtyard.

4.92 out of 5 average rating, 131 reviews

Gardens of Baron's Creek Unit A Main Street 1Blk

Right off Main St. you'll have the exquisite townhouse all to yourself! Within walking distance to the center of downtown with shopping, wine tasting, and restaurants. Enjoy your own PRIVATE courtyard with a PRIVATE splash pool (not heated) private hot tub & gas grill! Relax in the luxurious interiors with two fireplaces and stylish appointments. We are pet friendly! A small pet fee of $50 per pet is billed separately.

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, 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.

A private, tranquil pool area is surrounded by natural stone steps leading down to the water. Sun loungers are arranged around the pool, with umbrellas providing shade. A covered outdoor living space with a kitchen area is visible nearby, alongside trees offering greenery.

4.96 out of 5 average rating, 157 reviews

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

Cozy comfortable cottage one block from Main Street! Walking distance to popular restaurants, bars, shops and museums. Very convenient to wineries- perfect place for friend and family gatherings. Large backyard includes covered living space with fireplace and grill, private pool with hot tub, fire pit sitting area, and plenty of space for lawn games. You will feel right at home at the Henning Haus!