Performance indicators for the Upland short-term rental market based on reliable data.
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The highest-performing listings in Upland.
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Challenging to Investors
Upland's STR regulations are technically legal but constrained by significant investor limitations including mandatory primary residence status, un-hosted stay caps of 120 days annually, prohibition of ADU rentals, and multi-step permitting requiring business license, TOT certificate, AUP, and inspection. The city has structured processes but actively discourages ADU STR use and imposes operational rules like quarterly tax payments and detailed record-keeping that create meaningful compliance burdens for investors.
Local STR Agent
STR specialist · Upland, CA
Upland sits at the western edge of San Bernardino County in Southern California, in the Inland Empire region just east of Los Angeles County. With a population of approximately 77,000, the city rests at the foot of the San Gabriel Mountains and has long served as a quiet residential and commuter community within the greater Los Angeles orbit. About 35 to 40 miles east of downtown Los Angeles, Upland combines a small-town historic core with quick access to both the mountain wilderness of the Angeles National Forest and the urban conveniences of the broader Inland Empire. It is best known for its historic downtown along Foothill Boulevard, its foothill setting beneath Mt. Baldy, and its role as a convenient gateway to mountain recreation and regional attractions.
Just north of the city, the San Gabriel Mountains rise sharply, and the Angeles National Forest covers much of the rugged terrain beyond Upland's northern edge. Within an hour's drive, visitors can reach trailheads in the Mt. Baldy area, including the popular route to the summit of Mount San Antonio, the highest peak in the range at just over 10,000 feet. The forest offers hiking, camping, and winter recreation, making the mountains a major draw for outdoor enthusiasts who want to escape the urban basin without traveling far from the city.
A short drive west along the base of the foothills brings visitors to the neighboring city of Claremont, home to a cluster of prestigious liberal arts colleges collectively known as the Claremont Colleges. The city's walkable village district is lined with independent bookstores, cafes, and locally owned restaurants tucked beneath a canopy of mature trees, and it has long been a cultural hub for the region. Nearby, the California Botanic Garden (formerly Rancho Santa Ana Botanic Garden) showcases native California flora on more than 80 acres of landscaped grounds, drawing visitors interested in horticulture and conservation.
To the south and west, the city of Ontario is home to Ontario International Airport, one of the busiest airports in the Inland Empire, as well as the Ontario Convention Center and the Toyota Arena. Closer to home, Upland's own historic downtown stretches along Foothill Boulevard, the original Route 66 corridor through the region, and retains a number of early twentieth-century commercial buildings, antique shops, and locally owned restaurants. The Pacific Electric Inland Empire Trail, a converted rail-trail, runs through the city and connects to neighboring communities for walking, jogging, and cycling.
For short-term rental investors, Upland offers an appealing combination of affordability relative to coastal Southern California, a central location within the Inland Empire, and proximity to outdoor recreation, college-town amenities, and a major airport. Visitors can spend mornings hiking in the Angeles National Forest, afternoons browsing the bookshops of Claremont, and evenings dining along a historic stretch of Route 66, all within minutes of a single base.