Holiday rentals with a pool in Gillespie County

4.96 out of 5 average rating, 199 reviews

2 blk to Main.All season pool,sauna,hot tub

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!

A split-image showcases a cozy living area with a large television mounted on a dark feature wall and a warm seating arrangement. The outdoor space features a heated swim spa and comfortable patio seating surrounded by a well-maintained yard and landscaped stones.

4.96 out of 5 average rating, 105 reviews

Close to Main, Heated Pool, Firepit, 220EV outlet!

This 3 bedroom (6 beds)-2 bath home is the perfect spot for your family gatherings, friends trips, or the romantic getaway! Are you looking to unwind? You have options! Check out the growing cuisine of Fredericksburg, award-winning Texas wines, or choose to relax in our newly installed swim spa . What is a swim spa? Your choice whether you want a cooling swimming pool or a heated, jetted pool. This is the place for your next vacation! *No longer a hot tub but still heated swim spa!

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, 231 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.

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, 299 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, 144 reviews

Hot tub, Cowboy Pool, Pet Friendly, Close to Town

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

Superhost

A vintage Airstream is parked on a gravel surface, reflecting sunlight. In the foreground, a cowboy pool is visible, with a person relaxing inside. The backdrop features an open field under a clear blue sky, creating a spacious and serene outdoor environment.

Tiny home in Fredericksburg

4.76 out of 5 average rating, 103 reviews

Airstream Glamping Near Town!

Are you looking for a fun, unique and instaworthy place to stay while in Fredericksburg? If so this is the place for you. Newley Renovated Vintage Airstream parked on our 7 acre compound just a quick 7 minuet drive to the Heart of Main Street. The interior has been completely redone with style and comfort. The perfect retreat for couples or friends who are looking for a non-traditional stay. Unwind after a long day of shopping and sight seeing in the cowboy pool while star gazing.

A modern building is presented with a spacious covered porch supported by sturdy columns. Dark railing surrounds the porch, where a set of chairs is visible. The structure is surrounded by natural landscaping, featuring trees and a gravel pathway leading to the entrance.

4.97 out of 5 average rating, 101 reviews

Oak Casita in The Glades

Welcome to Oak Haus in The Glades on winery corridor. Take it easy at this unique and tranquil getaway. Enjoy wine at the fire pit or coffee on the porch, where deer might scamper by. Spend your time relaxing, playing games or swimming in the heated cowboy pool (which is a 10 foot stock tank) in the common leisure corral. Visit the 12 wineries, brewery or two distilleries that are within one and a half miles of Oak Haus. Fredericksburg is just a short drive away.

4.98 out of 5 average rating, 169 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

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.

5 out of 5 average rating, 258 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 ☀️

Treehouse in Fredericksburg

4.89 out of 5 average rating, 134 reviews

Mesquite Treehouse @ A-Frame Ranch

Escape to a modern A-frame treehouse just outside Fredericksburg. Nestled on 17 acres, The Mesquite 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, rainfall shower, luxe linens, and modern amenities. The perfect blend of nature and comfort awaits.

A charming cottage, painted in soft yellow, features dark green shutters and an inviting porch. Rocking chairs are positioned on the covered entry, surrounded by lush greenery. A white picket fence encloses the front yard, enhancing the home's welcoming exterior.

4.96 out of 5 average rating, 165 reviews

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!