Holiday rentals in Randolph AFB

The Plumeria Retreat on the Lake

This recently built 2-bedroom, 2-bath San Antonio vacation rental is the perfect home base for a relaxing retreat with family or friends! This home features FREE Level-2 EV (CCS) charging, 3 Smart TVs & a fully equipped kitchen. Sip your coffee from the deck & enjoy the lake and plumeria garden views. Hike local trails before heading out for shopping/sightseeing. *** Ask us about booking our optional retreat space** Please note: This property is on the 2nd floor & requires stairs to access.

Exclusive Loft

Discover the charm of this beautiful loft, boasting a modern design adorned with quality furniture. Enjoy a unique blend of privacy and seclusion, thanks to its exclusive connection to the main house—accessible only through a private exterior door. Perfectly sized for solo adventurers or cozy couples, this space comes equipped with a Smart TV (Netflix included), a mini-fridge and a microwave for your convenience. Plus, stay connected effortlessly with ultra-fast internet powered by Google Fiber.

PaPa’s Casita at SoJo Ranch

ADULTS ONLY Relax in style at our poolside casita, nestled on a micro-ranch near Randolph Air Force Base. Perfect for pilots in training, travel nurses, or short-term stays. Enjoy convenient access to the base or local activities while unwinding in your own private oasis. Complete with all the comforts of home, including a cozy queen bed, a single convertible bed, a full bathroom and a kitchenette, open access to the pool. Your stay at the casita promises relaxation, peace and some Texas fun!

The Randolph - Comfortable & chic 3bd/2br home

Welcome to the Randolph House in Converse, TX! Our home has been thoughtfully designed to provide a welcoming retreat for small families, groups of friends, military personnel, contractors, & traveling medical professionals looking to unwind & relax away from work. With its convenient location from the vibrant city of San Antonio, aka Military City, USA, you'll have easy access to the top attractions the area has to offer. Come experience comfort & your home away from home at the Randolph House!

Romantic Couples Cabin with Private Hot Tub

•Where love settles in and time slows down. •Grantham House is a romantic couples cabin designed for connection, comfort, and unforgettable moments. A guest favorite with outstanding reviews. Awarded Airbnb’s top 1% of homes. •Nestled in the Texas Hill Country, this private retreat offers beautiful views, a warm hot tub, and a cozy space made for two. •Whether you are celebrating something special or simply escaping the everyday, this is a place to relax, reconnect, and enjoy time together.

The Glory Nest w/pool and pickleball court

The Glory Nest was built in 2024, boasts of a 180 acre nature park as her front yard and is part of Olliewoods Oasis - a mix and match of colorful and eclectic sleeping options. The property is 2.5 acres and is adjacent to the park. It also offers a pool, 30x30 covered pavilion, covered pickleball court, volleyball, outdoor hot water shower and toilet/shower house (Groovy Go Go). Board games/movies/yard games provided along with pickleball paddles to try the fastest growing sport in America!

Cibolo Creek Country Cottage on over 2 acres

It's a two bedroom one bath house with a back deck and front porch on over two beautiful acres. Bordered by farmland, and across the road is Crescent Bend Nature Park. The park is a great place for bird watching, walking, jogging, bike riding and fishing. We are only minutes away from Randolph AFB and historic Main St. Cibolo with unique dining and weekend entertainment options. The cottage is a 20 minute drive to downtown San Antonio, New Braunfels or Fort Sam Houston. Owners live next door.

Texy-Mexy Bungalow

Welcome to our charming Texy-Mexy Bungalow, where the spirit of the Lone Star State meets the vibrant flavors of Mexico! Step into this cozy one-level retreat and immerse yourself in the warm and inviting ambiance inspired by the rich cultural fusion of Texas and Mexico. Located no more than 15 minutes from all major sites, you'll be able to explore the city easily! The bungalow is perfect for military families waiting on their homes or for those who just love San Antonio! Bienvenido!

ArtLens Casa-Billiards-Campfire-TVs-bbq-Swings-WD

4-Bedroom-Family Friendly-10 guests 👶Pack-and-play, Highchair Enjoy entertainment 🎼Bluetooth in Ceiling Surround sound 🎱Pool table 🎲Board games 🔥Fire pit 👉Play set 👉Outdoor barbecue 👉Fully-equipped kitchen 👕Washer Dryer 🚗10 min👉Randolph 🚗30 min👉Six Flags🎡 🚗45 min👉Seaworld 🚗30 min👉Downtown San Antonio 🚗25 min👉New Braunfels/Schlitterbahn/Tubing 🚗30 min👉🛫 SAX 5⭐“Everything was great!” Add my listing to your wish list by clicking ❤ in the upper-right corner.

Stylish, Charming Home In The Heart of San Antonio

Featured in Condé Nast Traveler. Enjoy a newly remodeled and tastefully designed home in a charming, elegant neighborhood in the heart of San Antonio. Our home is located in the Alamo Heights neighborhood, known as one of the best places to live in San Antonio & surrounding areas. Relax in our warm and welcoming home which is in close proximity to downtown, the airport, and major go-to spots and top restaurants in the city. We hope you have a wonderful stay in our beautiful home!

Free Range Inn

The Free Range Inn is a perfect place for a cozy getaway! The suite is attached to our home, but your space is completely private (it has its own entrance, and a locked door separating the suite from the rest of the house). Your space includes a kitchenette, full bathroom, a queen sized bed, a workspace, internet, a dining area, complimentary coffee and tea, Roku TV, and complimentary paraben-free and sulfate-free shampoo, conditioner, & body wash. We hope you enjoy your stay!

Southern Charm - Homemade Banana Bread @ Check In!

You'll feel at home in our cozy, updated house located in a quiet neighborhood just minutes away from the following major highways: IH-35, IH-10, LOOP 1604, and Interstate 410. There are 5 Wal-Marts and 3 HEB grocery stores within a 5 mile radius. There are also quite a few city parks nearby, including one with a lake within a short walking distance. This home is also kid and baby friendly! We love catering to families, and making kiddos feel just as welcome!