
Vacation rentals with a pool in Gillespie County
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Top-rated rentals with a pool in Gillespie County
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*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!

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.

Winter Cheers with Wine, Heated Pool, Firepit!
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!

Ultra Modern & Enchanted! Tub + Pool + Location!
Imagine being immersed in a small enchanted forest only 100ās 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.

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

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

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.

Pecan Casita in The Glades
Welcome to Pecan Casita in The Glades on winery corridor. Take it easy at this unique and tranquil getaway. Enjoy wine around 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 2 distilleries that are within one and a half miles of Pecan Casita. Fredericksburg is a short drive away.

Beautiful Home, Pool, Hot Tub & Pet Friendly
Bachelorette Party? š„ Wine Tasting? š· Family Vacation? š” "Acorn Haus" in Fredericksburg awaits you! This 3BR gem boasts IG-worthy decor, king beds, expansive backyard, outdoor dining š½ļø, a 6-person hot tub š, new pool šāāļø elevating your stay to unparalleled luxury! Just minutes from Main Street, you're close to top restaurants š“, wineries, and attractions. Perfect for creating unforgettable moments. š Dive into the heart of Fredericksburg with us! š«

The Farmhouse: Modern Retreat in Fredericksburg
Welcome to The Farmhouse, a modernized 1930ās 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

Tejas Hills Guest Haus #2 | Hill Country + Pool
POOL RETREAT | NEAR MAIN STREET | HILL COUNTRY ESCAPE Relax at Tejas Hills Guest Haus #2 ā a cozy 2BR/1BA Hill Country retreat with a private pool and spacious backyard. Conveniently located near Fredericksburgās Main Street, local shops, and restaurants. Minutes from Wine Road 290 wineries, breweries, and Enchanted Rock. The perfect spot to unwind, sip local wine, and soak up the Hill Country sunshine with family, friends, or that special someone.

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 āļø
Popular amenities for Gillespie County rentals with a pool
House rentals with a pool

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

Close to Main- family friendly with pool & hot tub

Taylor Haus - Hot Tub & Comfort!

4BR: Hot tub, Pool, Fireplaces, Grill, Family Fun!

Relaxing 5-acre Retreat | Guest House | Game Room

Pool | Oasis Backyard | 3 min to Main

Barrel Sauna & Hot Tub, 8 blocks to Main St.

LuxeHaus with Pool and Spa
Other vacation rentals with a pool

The Ranch House - Camp Hideaway Fredericksburg

Napa Valley Station | Pool & Rooftop Patio

Texas Wine Hill Country Private 12 Acre Experience

Tickled Pink GLAM House close to Main

Pickleball, Bocceball, Firepit, Pool, Pets, Hottub

Pickleball, Pool, HotTub, Movie Projector- By Main

Fritzie at Town Creek - 1.5 Blks off Main

The Wine House Luxury Pool & Hot Tub, EV Charger!
Destinations to explore
- Pet-friendly rentalsĀ Gillespie County
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- Rentals with a fire pitĀ Gillespie County
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- Rentals with poolsĀ Texas
- Rentals with poolsĀ United States
- Guadalupe River State Park
- Texas Wine Collective
- Longhorn Cavern State Park
- Hidden Falls Adventure Park
- Pedernales Falls State Park
- Inks Lake State Park
- Hamilton Pool Preserve
- Tapatio Springs Hill Country Golf Course
- Escondido Golf & Lake Club
- Blanco State Park
- National Museum of the Pacific War
- Becker Vineyards
- Fall Creek Vineyards, Tow
- Hilmy Cellars - Vineyards, Winery & Tasting Room
- Kuhlman Cellars
- Signor Vineyards
- Pedernales Cellars
- Ron Yates Wines
- William Chris Vineyards
- Spicewood Vineyards
- Bending Branch Winery
- Inwood Estates Vineyards Winery & Bistro
- Grape Creek Vineyards
- Slate Mill Wine Collective




