Vacation rentals with a pool in Gillespie County

A private in-ground pool is surrounded by a concrete deck featuring a shaded outdoor dining area. Several lounge chairs are arranged nearby, with splashes of water cascading from the pool's jets.

4.95 out of 5 average rating, 105 reviews

Close to Main- Pool, Hot Tub, Family Friendly

Located just off Main Street, Bell Street Bungalow is the perfect destination for a girls getaway, couple's retreat, or family weekend in Texas Wine Country. The home has 2 bedrooms, a bathroom, and game room in the main house in addition to a 1 bed/1 bath cottage in the backyard; both included in your stay. Enjoy the hill country outdoors by the private in-ground pool, hot tub, fire pit, and grill area. The home is a mile from the best downtown destinations and a short drive to many wineries.

ValueLocationAccuracy

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, 233 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.

LocationValueKitchen

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, 318 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

FamilyLocationComfort

Superhost

The outdoor patio features a cowboy pool surrounded by greenery and a shade umbrella. Two hanging chairs provide seating, and a cozy blanket is draped over one. Strings of lights illuminate the space, enhancing the inviting atmosphere under the evening sky.

4.87 out of 5 average rating, 164 reviews

Hot Tub, Cowboy Pool, Pet Friendly, Country Views!

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

ValueFamilyDecor

An outdoor gathering area is surrounded by towering oak trees, featuring a circular fire pit made of stone. Several comfortable chairs are arranged around the fire pit, creating an inviting space for socializing. A rustic structure with a grill is visible in the background.

4.96 out of 5 average rating, 99 reviews

Large Groups-Pool/Spa/Game Room/Guest House

**Luxury Retreat: Modern Farmhouse with Casita & Resort-Style Amenities** Escape to this Luxury farmhouse with a charming casita (full 1 bedroom apartment above game room), nestled among oak trees just outside of town. Enjoy the game room with twin bunks and twin rollaway cots, heated pool, fire pit, and spa house with jacuzzi. Perfect for family or friends—your serene getaway awaits! Book now! 6 Min Drive -Main Street 15 Min Drive- Grape Creek Vineyards 33 Min Drive- Enchanted Rock

FamilyLocationAccess

4.94 out of 5 average rating, 156 reviews

Ranch in Fredericksburg

Grand Oaks Ranch · Pool·Spa · Game Barn · Animals

Built beginning in 1848 and over several generations, Grand Oaks Ranch is a historic limestone farmhouse sleeping 16 on 22 private Hill Country acre with a resort pool, hot tub, fire pit, and barn. Unwind poolside, sip wine at sunset, roast s'mores under the stars, or challenge your crew to a late-night ping pong battle in the barn. Friendly cows, goats, and horses roam the property. Minutes from Main Street and the wineries. Authentic Texas ranch life with every comfort you'd want.

LocationFamilyLayout

4.97 out of 5 average rating, 163 reviews

Fredericksburg 3BR•Pool•Hot Tub• Wine Trail• Pets

Your Fredericksburg basecamp for wine country, bachelorette weekends, and family trips. Acorn Haus is a 3-bedroom modern farmhouse with three king suites, sleeping 8 with a private heated pool and hot tub, minutes from historic Main Street and the 290 wine trail. Boho-chic interiors, full kitchen, fast WiFi, free parking, and dog-friendly. Walk to tasting rooms and dinner, then come home to the pool. Every couple gets a king - nobody draws the short straw. Easy Instant Book.

LocationFamilyOutdoor spaces

Townhouse in Fredericksburg

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.

4.91 out of 5 average rating, 142 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.

ValueFamilyAir conditioning

Superhost

A modern A-frame interior features a spacious living area with large windows offering views of surrounding greens. A dining table is set for four, while a light grey sofa invites relaxation. Natural wood accents enhance the atmosphere, complementing the design's rustic elegance.

Cabin in Fredericksburg

4.9 out of 5 average rating, 337 reviews

Hill Country A-Frame Cabin | Pool, Sauna & Nature

🌄 Modern A-Frame cabin on 17 scenic acres near Fredericksburg 🛏️ Sleeps up to 9 with 3 bedrooms + loft + sofa bed 🌿 Private patio with grill, fire pit & stock tank pool (heated option) 🧖 Access to shared cedar sauna on-site ☕ Fully equipped kitchen with local Hill Country coffee 🚗 Easy self check-in & on-site parking 💕 Family-friendly with loft hangout 🌌 Incredible stargazing in a Dark Sky Community 🦌 Peaceful Hill Country setting minutes from Main Street

FamilyLocationCheck-in

4.97 out of 5 average rating, 191 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

ValueLocationAir conditioning

Cottage in Fredericksburg

4.99 out of 5 average rating, 146 reviews

WALK to Main/Restaurants/Shops POOL/HOT TUB Sleep6

This will be your favorite! Experience the charm of Fredericksburg Cottage, nestled in the heart of Fredericksburg. This curated 3-bed, 2 bath Craftsman style bungalow offers the perfect blend of vintage charm & modern amenities for your next getaway. The Cottage is walking distance to many of the finest dining establishments and 0.06 miles from Main Street with all its offerings. Book now to secure your stay today!

LocationFamilyView

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.