Family-friendly holiday rentals in Dripping Springs

NEW Chic, Luxury Home with Pool - Howard Ranch!

This unique + stylish modern farmhouse has you living in the lap of luxury! Breeze out of your designer bedroom (one of TWO primary suites!) into your gorgeous bathroom, then wander out to one of TWO decked out kitchens for coffee or tea, cook a few eggs from the chicken coop just on the other side of the driveway, then meander outside for a splash in the pool to stretch your legs or stroll the property on the walking trails! Close to wineries, wedding venues, and hill country beauty/adventures!

Kitchen · Family · Access

Modern Aframe Tucked in Nature **hot tub & view**

Perched high on a hill overlooking the gorgeous TX Hill Country sits the most stunning A-frame you ever did see. With a mix of mid-century style and artsy touches, this space is gorgeous. The cabin is tucked into a pocket of nature surrounded by 3 acres of oaks, elms, and junipers. The expansive front windows and raised deck provide and incredible sunset view across the hills and dark sky lighting sets the stage for breathtaking starry skies. The hot tub and outdoor shower is icing on the cake!

Indoor spaces · Kitchen · Value

Private Retreat 5 Acres 2 King/1Q +Firepit

Gorgeous Escape while convenient to All activities.. Wedding Venues, Breweries, Wineries & all that Dripping Springs has to offer. Hiking, mountain biking & climbing nearby for outdoor enthusiasts. 30 min to Austin. 2 Kings & 1 Queen. Great for peeping stars & Wildlife! Indoor Fireplace, outdoor Firepit. Long term rentals welcome. Centrally located to Wimberley, Fredericksburg, Johnson City, Pedernales Falls, Mercer Street & more. Leaving is the hardest part! *Burn bans may impact use of fire

Kitchen · Indoor spaces · Location

Honkey's Hideout @Ranch225-Meet Honkey the Donkey

Welcome to the home of the World Famous Honkey the Donkey! Our home is located on 25 acres, and is home to our pet miniature donkey, Honkey, as well as goats, dogs, barn kitties, and horse companions that all LOVE to meet new people! You can get your fill of all the local wineries, breweries, and scenery the hill country has to offer. If you are looking for a place to unwind, take in the beauty of the hill country, and still be within 45 minutes of downtown Austin, this is the place for you!

Family · Kitchen · Biking

Hill Country Oasis: Home Theater/Pickleball 1.5 ac

Hill Country Oasis - 1.5 acres Heart of The Hill Country. New Home Theatre/Pickle/Basketball Court! This unique property has 2 houses consisting of a main and guest house with the pool and hot tub sitting between both houses. Perfect for larger groups & multifamily units looking to have their own space. Landscape features a manicured outdoor living area, putting green and playscape. Plenty of space for the entire family to enjoy! Hill Country Oasis in the Heart of The Hill County!

Family · Kitchen · View

Dripping Springs Oasis • Hot Tub, Pool • Austin

Natural light abounds in this modern hill country home! Explore 30 acres of stunning oaks and seasonal wildflowers. Soak in your private Jacuzzi on the ridge, or take a cool plunge in the dip pool. The outdoor sofa is positioned for ultimate bird watching and book reading. Grill outside, cook inside, or venture out to one of the nearby wineries, distilleries or restaurants. But when the sun dips low, get ready for unmatched sunsets and the starriest Texas skies! Welcome to bliss, y’all.

Family · Kitchen · Check-in

10-acre Hill Country Retreat w/ Views, Pool, & Spa

Enjoy the peaceful ambiance of the Texas Hill Country. The house is on 10 acres and sits on a hill with breathtaking views, wildlife, and natural surroundings. Thoughtfully decorated with both rustic and modern elements. Enjoy the tranquility of the country and modern touches like a fully stocked kitchen, fast internet, and luxurious bedding. Close by are the famous Hamilton Pools and countless wineries / distilleries to explore. Perfect for families, couples, or a group of friends.

Family · Kitchen · Pool

Modern Hill Country Retreat

Enjoy a relaxing vacation in Dripping Springs! Our home is located about 11 minutes from downtown Dripping Springs and about 12 minutes from beautiful Hamilton Pool Preserve. We are a close distance to many wineries, breweries, and distilleries. The back yard has an amazing view of the hill country! Gatherings for events are an option but pre approval is required. There will be an additional fee charged based on the group size. Please let us know if you have any questions!

Family · Indoor spaces · Access

Luxury Hilltop Casita - Endless Views

Escape city life,indulge into nature on the secluded porch,take in the views and abundant wildlife! Our custom,European inspired home sits high on a hilltop offering miles of views and gorgeous sunsets.Centrally located 20 min from Austin, 20 min from Wimberley & near many wedding venues.Relax in the hammocks, drink coffee on the patio or do yoga on the porch.Breathe in the fresh air & enjoy.Our goal is to create a memorable experience for you and to share our slice of heaven .

Family · Indoor spaces · Value

Day Drippin' Farm-stay | Rainwater| New Build

Situated on one acre of fenced yard, our cozy retreat offers the perfect blend of Texas country charm and modern amenities. Built in 2023, our home features chemical-free rainwater collection, a whole-home propane back-up generator, and top-of-the-line appliances for your convenience. Check-in with your personal code on the keyless entry in the covered carport. We are a family owned business which means we oversee every turnover, and go the extra mile to welcome you.

Indoor spaces · Family · River

Three Hearts Casita

Retreat to a luxe rustic casita on acreage in Dripping Springs surrounded by beautiful stone sculpture. Located next door to a winery and minutes from more tasting rooms and Dripping Springs Distilling. Inside, textured stucco with limestone insets, natural hardwood floors, and curated finishes make this cozy space feel inviting. Perfect to gather, unwind, and stargaze after a day of sipping and exploring the Texas Hill Country.

Indoor spaces · Kitchen · Walkability

3 Sisters Hill Country Cottage

Come stay at the 3 Sisters Cottage and enjoy a relaxing time in the Texas Hill Country. Incredible views from the back porch where you can hear cicadas singing in the summer, deer roaming on the property, and rolling hills covered by beautiful Oak trees. Less than 15 minutes from Downtown Drippin', 15 minutes from Hamilton Pool Preserve, 10 minutes from Treaty Oak Distillery, and 20 minutes to Driftwood Vineyards and more!

Family · Indoor spaces · Outdoor spaces