Vacation rentals with a pool in Gillespie County

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!

4.94 out of 5 average rating, 148 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.

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, 228 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 covered outdoor living space features a combination of comfortable seating and a coffee table, surrounded by natural wooden walls. Ceiling fans are present to provide airflow. Soft lighting from string lights creates a welcoming ambiance, enhancing the area’s connection to the surrounding garden.

4.99 out of 5 average rating, 288 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, 136 reviews

Hot Tub, Cowboy Pool, Pet Friendly, Fire Pit!

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

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

Luxury Historic Estate-Pool & Hot Tub, 2/3 acre

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!

4.97 out of 5 average rating, 105 reviews

Beautiful Home, Pool, Hot Tub & Pet Friendly

Bachelorette Party? 🥂 Wine Tasting? 🍷 Family Vacation? 🏡 "Acorn Haus" in Fredericksburg awaits you! This 3BR gem boasts IG-worthy decor, king beds, expansive backyard, outdoor dining 🍽️, a 6-person hot tub 🛁, new pool 🏊‍♂️ elevating your stay to unparalleled luxury! Just minutes from Main Street, you're close to top restaurants 🍴, wineries, and attractions. Perfect for creating unforgettable moments. 🎊 Dive into the heart of Fredericksburg with us! 💫

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, 223 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, 132 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

4.95 out of 5 average rating, 133 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 collage of The Birdhouse showcases the inviting outdoor space featuring a wooden deck with a cowboy pool and a hot tub. Inside, a modern kitchen with wooden shelving and a spacious sleeping area with a patterned duvet cover and natural light highlights the home's comfort.