Holiday rentals with a pool in Gillespie County

4.94 out of 5 average rating, 144 reviews

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.

Treehouse in Fredericksburg

4.95 out of 5 average rating, 110 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

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.

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

4.88 out of 5 average rating, 129 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

Townhouse in Fredericksburg

4.89 out of 5 average rating, 104 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.

Place to stay in Fredericksburg

4.99 out of 5 average rating, 433 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.

5 out of 5 average rating, 200 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

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.

4.94 out of 5 average rating, 263 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!

Farm stay in Fredericksburg

4.95 out of 5 average rating, 289 reviews

Stunning Fredericksburg Ranch House with POOL

Guests love staying here at Rose Ranch because of the proximity to many wineries, Alstadt Brewery, the amazing views, peacefulness of the ranch, the hot tub drinking your favorite beverage and the night skies for star gazing, wild animals roaming by, our sweet donkeys and horses, and the big beautiful front porch to dream and sip coffee in the morning!

Holiday rentals for every style

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Kick off your hiking boots at these rustic lodgings

Popular amenities for Gillespie County rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.91 out of 5 average rating, 128 reviews

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

CourtneyRating, 5 stars1 month 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!

4.97 out of 5 average rating, 62 reviews

Chastain Haus: Pool and Hot tub with all king beds

KatieRating, 5 stars1 month ago

Fantastic place and fabulous host. We’ll definitely be back!

5 out of 5 average rating, 27 reviews

3BR Scenic Setting w/ New Pool, 5 Mins to Main St!

KellyRating, 5 stars1 month ago

Great place to stay! Plenty of room and we felt right at home. Great hosts, very responsive, and great recommendations.

5 out of 5 average rating, 16 reviews

ThistleOaks Hillside Escape with Pool & Wildlife

AndreaRating, 5 stars3 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!

5 out of 5 average rating, 20 reviews

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

JoseRating, 5 stars6 days ago

This place was absolutely top-notch! From the moment we arrived, it felt like home—clean, beautifully organized, and welcoming. The pool was spotless and perfect for relaxing after a long day. One of the highlights was the Green Egg grill on the premises, we had a great time barbecuing and enjoying the outdoor space. Check-in and check-out were seamless, which made everything stress-free. Overall, this stay truly enhanced our trip. Highly recommend and would definitely come back!

4.93 out of 5 average rating, 27 reviews

Sale 3+ Nights! Pool | Firepit | Pets | Games

MalloryRating, 5 stars1 week ago

My family and I loved staying here, and would definitely stay again! From the privacy fenced backyard (perfect for our dog), to the pool which my kids swim in every day, to the perfect location to Main St. and Enchanted Rock, to the cleanliness and fast response time of Lauren and Matt, it was a 10 out of 10 stay. We can't wait to come back!

4.93 out of 5 average rating, 68 reviews

Heated Pool | Hot Tub | 3 min to Main

ZeeRating, 5 stars2 months ago

We had a great friend's reunion! The house was very clean and full of amenities. We loved used the fire pit and pool/hot tub every night. The backyard was peaceful and clean. We had coffee at both the outdoor and indoor tables. Wonderful experience.