Family-friendly holiday rentals in Kendall County

Relax and Enjoy the Views of the Hill Country

Set on a cliff above the Guadalupe River this private guesthouse with sweeping vistas is your Hill Country getaway. This home was designed for guests rest, relaxation and fun. Conveniently located near shopping, dining and outdoor activities although you may never want to leave the peace and quiet. Set on a cliff above the Guadalupe River this private guesthouse with sweeping vistas is your Hill Country getaway. This home was designed for guests rest, relaxation and fun. Conveniently located near shopping, dining and outdoor activities although you may never want to leave the peace and quiet. Take in the incredible views of the river, ranch and Hill Country from the custom pool and spa. One of a kind Texas views in a truly unique home make this an unforgettable Hill Country destination. See this house in the just released book "Spectacular Weekend Getaways of Texas" by Jolie Berry of Signature Boutique Books. Cliff Haven on the Guadalupe. In the middle of nowhere and near everything sums up this home. Very close to local shopping and dining. This guest house is located on 2.5 acres over 65 feet away from the main house in a safe and quiet community in Spring Branch Texas. Use it as your launching pad to visit the Hill Country, New Braunfels and San Antonio or just stay and unwind. This home was designed and appointed for the absolute best stay. Relax in the pool, enjoy the spa, grill a steak and enjoy drinks next to the fire. - Private Pool and Spa - Private Courtyard with Stone Fire Pit and Outdoor Seating - Outdoor Grill - Fully Equipped Kitchen - "Texas Living Room" Air Conditioned Finished Garage with Full View Glass Door, Pool Table, Sofa, Dining Table and Chairs, 60" TV, Mini Fridge, Ice Maker and Full Bath - High Quality Bedding and Pillows W.O.R.D. Permit #L1442 Guests have complete access to the entire home. The pool and spa is also for the exclusive use of the guests. The house is a separate very private guest house of the main home 65 feet away from main home. I value my guests privacy but I'm always available to answer questions or fill you in on all the cool things to do around here. This home is in a very quiet neighborhood. It has a very country type feel with deer and other wildlife readily seen. Home is available by car only and there is no public transportation or Uber available. This home is located about 35 minutes from downtown San Antonio. There are many parks and river access areas near the house. It's a great place to bike and run with awesome hills and flats. Great local restaurants and bars nearby and within a short drive.

Romantic Retreat | Hot Tub, Sauna + Outdoor Shower

One of the most loved romantic cabins on Airbnb, designed for couples who want to slow down, reconnect, and experience something different. Soak under the stars in your private hot tub, sip wine by the fire pit, and wake to deer just outside your window. This peaceful Hill Country retreat blends luxury, nature, and intentional design for an unforgettable stay. ✨ Elevate your stay with curated add-ons like our Sip + Soak experience, stargazing kit, or celebration setups, available after booking.

Dog Trot Guest Suites on the RW Ranch

Welcome to the hilltop on our 135 acre ranch. We are located in the heart of the Texas Hill Country with close proximity to everything! Our Dog Trot Guest Suites consists of 2 suites each with a queen bed, an additional sleeping area (daybed or trunnel) and private bath. Our 180 deg views are spectacular and the stars at night are big and bright! We are a short distance from Old Tunnel State Park, James Kiehl River Park, Sister Creek Winery, foodie restaurants and caves. Hope to see you soon!

Buffalo Haus - Downtown charm 2-bedroom bungalow

A charming home on a quiet street only six blocks from Main Street's shopping and restaurants. You can rest comfortably in a king or queen size bed and wake to enjoy the stocked coffee bar. If this is a working vacation, you will love the workspace and high speed wifi. While we're minutes away from River Road and its many dining options, you may decide to stay in and use the full kitchen. Either way you'll love relaxing on the large patio under the party lights. Dog friendly home.

Feed Deer Daily |Peaceful Hill Country Cozy Cabin

Nestled under towering oaks just 7 minutes from Boerne, the Cozy Oak Cottage offers a peaceful Hill Country escape where nature and comfort meet. Sip coffee as deer wander by, spot our friendly free-range chickens exploring the grounds, and enjoy the beautiful wild birds that visit the birdbath. A stylish, cozy interior, fast WiFi, and warm, thoughtful touches create a stay where guests feel genuinely cared for from the moment they arrive. Tap ❤️ and book your serene retreat today.

Haven House - Home near Guadalupe River St Park

Beautiful and comfortable, this gorgeous getaway is in the heart of Texas hill country, one mile south of Guadalupe St Park and next to the beautiful Park 31 wedding venue. We are minutes from small towns and a big city that offers unique and multicultural experiences, shopping, dining, and recreation. Guadalupe River Park is easily accessible and offers water recreation, camping, and day hikes. As a working horse ranch, you will enjoy the close interactions with our animals!

*SALE THIS WKND!* The Trailer: Gallery & Art House

1/2 MILE WALK TO HILL COUNTRY MILE! Created to benefit the best local artists of Boerne and SA, The Trailer: Gallery & Art House (currently ft. Jorge Godinez of SATX) stands alone as a 1-of-a-kind immersive art experience. Put on your walking shoes and cross the street to stroll along the creek straight down to the antique shops, boutiques, 5-star restaurants, local breweries, etc., that the vibrant Historical District of Downtown Boerne has to offer.

Hill Country Carriage House

We have everything you need for a romantic getaway, business travel or fun family time. We live in a wonderful neighborhood where deer and chickens roam free. We are about a 5 minute drive to/from Main Street and in the very heart of the Texas Hill Country. Southern hospitality, hiking trails, wineries, brew haus, music venues and everything the great HC offers is here. Come be our guest! Read entire site for info! We look forward to meeting you.

Secluded Hill Country Cabin | Hot Tub + Stargazing

Cowboys & Dreamers is a secluded luxury retreat tucked into the rolling hills of Kendalia — designed for slow mornings, dark skies, and unforgettable Texas Hill Country sunsets. Whether you’re planning a romantic getaway, wellness retreat, anniversary trip, weekend escape, or simply searching for a peaceful luxury cabin in the Texas Hill Country, Cowboys & Dreamers offers a stay that feels restorative, grounding, private, and unforgettable.

Blanco River Home - River view with new updates!

With a spacious back porch and sprawling yard with large pecan trees facing the beautiful Blanco River, this home provides a relaxing oasis for a week-end getaway or longer stay. Walk to the historic Blanco town square, stroll or picnic in the park or explore the scenic Hill Country. Enjoy the recent refresh which includes floor to ceiling windows in the living area, vinyl plank flooring throughout and updates to both bathrooms

Luxe Yurt, heater, w/ hot tub, sunset&hill country

Escape the hustle and melt your cares away in the hot tub at this unique luxury yurt in Boerne! A nature lover’s retreat, butterflies abound and two mini splits keep you perfectly cool or cozy. Just 2 miles to downtown Boerne, 14 to San Antonio, and 36 to Fredericksburg—it’s the perfect spot to reconnect with nature. Enjoy fresh eggs from our hens, homemade bread, and our signature goat milk soap during your stay.

Gray Hund Acres- Dog Friendly & 17 private acres

Rest and relax in the Texas Hill Country at Gray Hund Acres. You’ll enjoy your stay at this unique and beautiful timber frame, rock farmhouse which sits on 17 acres. This home can accommodate 6 guests. Enjoy the breeze and sunset with a drink in hand, on 1 of the 3 porch/patios. The Blanco River and downtown are just a short 10-minute drive. You’ll love the views and peace and quiet at Gray Hund Acres.