Vacation rentals with a pool in Gillespie County

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Top-rated rentals with a pool in Gillespie County

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

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.

Home in Fredericksburg

4.91 out of 5 average rating, 130 reviews

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

Beautiful Country Oasis Haus close to all the fun and has everything to make your stay in Fredericksburg the very best! Plenty of room for the entire group. Sleeps 10 comfortably! Outdoor space with pool with waterfall, giant hot tub, fire pit area, huge deck with picnic tables, game area and giant oak trees. Inside is a beautiful rustic theme with a big kitchen, master bathroom suite, cozy fireplace, TVs in all bedrooms, luxury linens and soft beds. Pet friendly! PLUS 7 cruiser bikes included.

Guest favorite

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

4.94 out of 5 average rating, 146 reviews

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

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.

Treehouse in Fredericksburg

4.94 out of 5 average rating, 119 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, 226 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.

Top guest favorite

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.

Home in Fredericksburg

4.99 out of 5 average rating, 279 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

Guest favorite

A clear view of the private heated pool surrounded by lounge chairs, colorful floaties, and towels. The clean pool reflects blue skies and is complemented by lush greenery in the background, alongside a split-level home featuring large windows that invite natural light.

Home in Fredericksburg

4.96 out of 5 average rating, 137 reviews

My Happy Place! One block off Main St!

Beautiful mid-century modern home with private heated pool (open Mar-Nov) one block from Main St in charming Fredericksburg, TX. This home is built modeling a Frank Lloyd Wright design with elements of the Hill Country incorporated into the structure. This 3 bedroom split level house has an open kitchen, living/dining area, large fenced yard with patio & gas grill and is an ideal vacation rental for families & friends. You're sure to make many happy memories here! STR Permit #8056000997

Guest favorite

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.

Home in Fredericksburg

4.93 out of 5 average rating, 146 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!!

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.

Home in Fredericksburg

4.88 out of 5 average rating, 133 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

Guest favorite

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.

Townhouse in Fredericksburg

4.9 out of 5 average rating, 109 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.

Top guest favorite

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.

Home in Fredericksburg

4.98 out of 5 average rating, 154 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

Top guest favorite

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.

Home in Fredericksburg

5 out of 5 average rating, 204 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 ☀️

Guest favorite

Home in Fredericksburg

4.94 out of 5 average rating, 273 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!