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The highest-performing listings in Longwood.
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Generally Investor friendly
Longwood permits STRs explicitly under Seminole County Ordinance 2020-14, providing clear legal framework with manageable registration at state/county levels. While requiring multiple licenses, safety equipment, and operational restrictions (occupancy limits, parking standards, noise rules), the compliance burden is moderate and achievable. Active code enforcement exists but the process is transparent and established, making STR investment viable for prepared operators.
Local STR Agent
STR specialist · Longwood, FL
Longwood is a small, tree-shaded city in Seminole County, Florida, situated in the northern reaches of the Orlando–Kissimmee–Sanford metropolitan area. With a population of approximately 15,000, it carries a quieter, more residential character than the bustling tourist corridors to the south, anchored by a leafy historic downtown and a strong sense of local community. The city is best known as a comfortable base for travelers who want to explore Central Florida's natural springs, lakes, and wildlife while still being within easy reach of Orlando's theme parks and urban offerings. Longwood sits roughly fifteen miles north of downtown Orlando along Interstate 4, making it a practical hub for visitors who prefer a calmer home base over a hotel near the attractions.
One of the most popular natural escapes in the area is Wekiva Springs State Park, located in adjacent Orange and Seminole counties about fifteen to twenty minutes west of Longwood. The park centers on a crystal-clear natural spring that feeds into the Wekiva River and offers swimming, snorkeling, canoeing, and wildlife watching in a setting that feels far removed from the state's commercial heart. Manatees, black bears, and a wide variety of wading birds are regularly spotted in and around the spring run.
Just a few minutes east of Longwood lies the Central Florida Zoo & Botanical Gardens in neighboring Sanford, which houses a diverse collection of animals, an aerial adventure course, and a butterfly garden. The zoo is compact enough to visit in a half-day but rich enough to entertain families with children, and its botanical grounds add a peaceful complement to the animal exhibits.
Sanford itself, immediately adjacent to Longwood, is worth a visit for its brick-paved downtown along Lake Monroe. The historic district is filled with locally owned restaurants, breweries, antique shops, and a waterfront promenade where visitors can stroll and watch boats come and go. The drive from Longwood to the center of Sanford typically takes less than fifteen minutes.
Slightly south of Longwood, Lake Jesup offers one of the largest freshwater lakes in the region and is famous for its dense population of alligators, which can be observed from boardwalks and guided airboat tours. It also functions as a popular spot for kayaking, birding, and sunset watching.
Longwood appeals to short-term-rental investors and visitors alike because it offers a rare combination of small-town calm, easy access to Central Florida's natural attractions, and a quick drive down I-4 to Orlando. Travelers who choose to stay here can spend a day at the springs, an evening dining in historic Sanford, and still make a morning theme-park reservation without ever feeling like they are in the middle of a tourist district.