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Highland, CA
Challenging To Investors
Local STR Agent
Local STR Agent

Important context: Highland, CA is a city within San Bernardino County. Within city limits, short-term rental (STR) operations are governed by the City of Highland’s municipal code; however, no Highland-specific STR regulations were provided in the content reviewed. In contrast, San Bernardino County (SBC) administers a mature STR program for properties in unincorporated mountain and desert regions of the county. Where city-specific rules are unavailable, county-level and state-level requirements apply. All information below is drawn strictly from the provided sources.
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Highland hosts earn a median $25,973/year with $127 ADR and 61% occupancy.
Top performers pull in $44,694+ per year.
See the full Highland market breakdownThe following steps reflect the SBC process for unincorporated mountain/desert properties. For Highland city properties, confirm local requirements with the city before proceeding.
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Highland is a suburban city in San Bernardino County, California, tucked into the southwestern foothills of the San Bernardino Mountains and forming part of the broader Inland Empire metropolitan area. With a population of approximately 55,000 residents, the city has a quiet, residential character defined by wide suburban streets, modest ranch-style homes, and views of pine-clad mountains rising to the north. Highland functions primarily as a bedroom community for the surrounding region and as a convenient gateway for travelers heading up into the San Bernardino National Forest and its mountain resort towns. It sits roughly 60 miles east of downtown Los Angeles and just a few miles north of San Bernardino, the county seat, putting it within easy reach of both the urban amenities of the Inland Empire and the high-country recreation of Southern California.
Just up the mountain from Highland, the San Bernardino National Forest spreads across more than 800,000 acres of pine forest, canyons, and alpine terrain. Visitors can reach the forest's lower trailheads in about 20 to 30 minutes, and the area offers hiking, mountain biking, and winter snow play at spots like Snow Valley Mountain Resort. The forest also shelters two of Southern California's most popular mountain lakes, making it the principal reason many travelers base themselves in Highland.
Lake Arrowhead is one of those destinations, sitting at roughly 5,100 feet in elevation about 30 miles northeast of Highland. The lake and the surrounding village attract visitors year-round for boating, fishing, and a small-town alpine atmosphere, and it typically takes around 50 minutes to reach by car via Highway 330.
Big Bear Lake lies further east in the same mountain range, about 55 miles from Highland and roughly an hour and a half away by car. The four-season resort area is known for its seven-mile lake, winter skiing and snowboarding at Bear Mountain and Snow Summit, and a walkable village filled with restaurants, shops, and the Big Bear Alpine Zoo, a rehabilitation facility for injured local wildlife.
Down the hill, the city of San Bernardino sits only about five miles south and offers cultural stops like the historic California Theatre of the Performing Arts and the Original McDonald's Site and Museum, a small museum at the location of the first franchised McDonald's restaurant. San Bernardino's Route 66 heritage also gives the area a layer of mid-century nostalgia worth exploring on a day trip.
Highland makes a compelling base for short-term rental investors because it sits at the intersection of two very different Southern California experiences: the affordability and accessibility of the Inland Empire, and the doorstep access to the San Bernardino Mountains' lakes, forests, and ski resorts. Guests who stay here can spend the morning hiking in the national forest, the afternoon on the water at Lake Arrowhead or Big Bear, and the evening back down in the lowlands enjoying dinner in San Bernardino or Redlands, all without having to commit to a single destination.
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