Performance indicators for the Annapolis short-term rental market based on reliable data.
Listings
Reliable / Active
Cap Rate
Middle-Earners Gross Yield
Revenue
Middle-Earners Revenue
Occupancy
Middle-Earners Occupancy
Home Value
Median Home Sale Price
Top Earners
Top-Earners Revenue
The highest-performing listings in Annapolis.
Loading top listings...
Challenging to Investors
Allowed but licensed and actively enforced; the proposed 10% block‑face concentration cap can restrict viable sites, and investors must navigate licensing, local lodging/sales taxes, and HOA approvals with evolving rules, adding compliance risk.
Local STR Agent
STR specialist · Annapolis, MO
Annapolis is a very small unincorporated community in Iron County, in the southeastern Ozark region of Missouri. With a population of just a few hundred residents, it carries the quiet, unhurried character typical of rural Ozark villages, and it is best understood as a gateway to the rugged natural scenery of the St. Francois Mountains rather than as a destination in its own right. The community sits roughly 90 miles south-southwest of St. Louis, making it a reasonable drive for travelers seeking an escape from the city without venturing too far from a major metropolitan area. Annapolis is also within about 25 miles of larger Ozark towns such as Ironton, the Iron County seat, and Fredericktown, which offer additional dining and services for visitors.
One of the closest and most rewarding natural attractions near Annapolis is Taum Sauk Mountain State Park, home to the highest point in Missouri at 1,772 feet. The park features the towering Mina Sauk Falls, the state's tallest waterfall, along with rugged hiking trails, backcountry camping, and dramatic views of the surrounding Ozark highlands. It lies only a short drive southwest of Annapolis, making it a natural day trip for guests interested in Missouri's most elevated terrain.
Just a few miles to the north of Annapolis, Elephant Rocks State Park offers a strikingly different landscape. The park is named for a series of massive, billion-year-old granite boulders stacked along a quarter-mile Braille Trail, the first in Missouri designed for visitors with visual impairments. The rounded red boulders attract rock climbers, photographers, and families who enjoy scrambling across the smooth, weather-rounded stone.
A slightly longer outing from Annapolis is Johnson Shut-Ins State Park, located about 30 miles west in Reynolds County. The park is known for its natural water slides and swimming holes formed where the Black River tumbles through a narrow gorge of volcanic rock, creating one of the most popular summer swimming destinations in the Ozarks. The surrounding terrain includes deep forests and easy hiking trails that showcase the geological character of the region.
Annapolis's appeal for short-term rental owners lies in this very combination: a genuinely quiet, off-the-beaten-path base that is within easy reach of some of Missouri's most distinctive outdoor destinations. Guests who choose to stay here can spend their days exploring state parks, swimming in the Black River, and hiking through the Mark Twain National Forest, which blankets much of Iron County, before returning to a peaceful rural setting that feels far removed from the pace of the city.