Holiday rentals with a pool in Gillespie County

*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!

Rustic Soul, Modern Comfort | Relax on the Ranch

Step back in time, with the modern comforts you love, at Grand Oaks Ranch, an 1848 homestead turned spacious 5-bedroom, 3-bath retreat on 22 peaceful acres. Unwind by the pool, sip wine at sunset, roast s’mores in the fire pit, or take on your friends in a late-night ping pong battle. Just minutes from Main Street and wineries, this authentic ranch offers rustic charm, wide-open views & friendly cows, goats, and horses. Whether heading out or staying in, it’s the perfect Hill Country escape.

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.

Luxe Historic Estate-Pool & Hot Tub-Walk to Main!

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!

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! 💫

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

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.

3B/2B Pool & Hot Tub- 1 BLK to Main!

Cozy comfortable cottage one block from Main Street! Walking distance to popular restaurants, bars, shops and museums. Very convenient to wineries- perfect place for friend and family gatherings. Large backyard includes covered living space with fireplace and grill, private pool with hot tub, fire pit sitting area, and plenty of space for lawn games. You will feel right at home at the Henning Haus!

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!