Vacation rentals with a pool in Gillespie County

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.

Value · Location · Kitchen

Upscale|Swimspa-pool|sauna|hot tub|2 blk to Main

Harmony is a gorgeous upscale home located two blocks from Main Street. The home has been custom designed to host families, couples, and friend getaways. Enjoy the open layout, spacious bedrooms and fantastic dining and kitchen areas this gorgeous has to offer. Step outside to your private backyard relaxation oasis featuring a swimspa pool, sauna, hot tub, spacious deck, sipping wine around the fire pit, or enjoying a hot cup of coffee on the front porch! Book your Hill Country getaway today!

Value · Family · Sleep quality

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

Family · Location · Biking

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.

Family · Location · Hospitality

Luxury Historic Estate-Pool & Hot Tub-13 guests

History meets Luxury at Sweet Escape! * Restored Historic 4 bedroom/3 bath for up to 13 guests on a 2/3 acre Estate IN TOWN. * 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!

Value · Family · Hospitality

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

Location · Value · Pool

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.

Family · Location · Cleanliness

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.

Location · Family · Decor

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.

Family · Location · Backyard

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

Location · Value · Air conditioning

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.

Location · Value · Outdoor spaces

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.

Value · Location · Checkout