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Maitland, FL
Generally Investor Friendly
Local STR Agent
Local STR Agent

Yes, short-term rentals are allowed in Maitland, Florida with proper permitting and compliance with city regulations. The City of Maitland permits short-term rentals (defined as rentals of less than 30 days) through a formal certificate application process, provided owners meet all requirements including owner-occupancy, insurance, safety standards, and community notification procedures.
Maitland hosts earn a median $45,526/year with $220 ADR and 72% occupancy.
Top performers pull in $85,746+ per year.
See the full Maitland market breakdownCommunity Development Department
Address: 1776 Independence Lane, Maitland, FL 32751
Phone: (407) 539-6248
Fax: (407) 539-6275
Website: www.itsmymaitland.com
Phone: (407) 539-6150
Code Enforcement
Phone: [Contact through main police number - not provided in source]
Address: [Contact through city website for specific department contact]
Contact through Orange County government channels
This guide reflects the current regulatory environment as of the provided source materials. Investors should verify current requirements with local authorities before proceeding with any STR investment in the Maitland area.
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Maitland is a small, leafy city in Orange County, Florida, with a population of approximately 17,000 to 19,000 residents. Tucked into the northern edge of the Orlando metropolitan area, it sits about six miles north of downtown Orlando and a little under twenty miles west of the larger suburban hub of Winter Park. Best known for its chain of scenic lakes, its historic art community, and its role as a calm residential base near Central Florida's major attractions, Maitland offers a quieter alternative to the busier tourist corridors to the south while still keeping the region's biggest draws within easy reach.
The Art & History Museums of Maitland is one of the city's most distinctive cultural landmarks. Founded in 1937 by artist and illustrator Jules Andre Smith as the Research Studio, the property is now operated as a museum complex and includes the architecturally striking Maitland Art Center, with its Mayan-inspired courtyards, a working chapel, and rotating exhibitions. Listed on the National Register of Historic Places, the museum is located within Maitland itself, just a short drive from most points in the city (Art & History Museums of Maitland).
A few minutes away, the Audubon Center for Birds of Prey offers a more naturalistic counterpoint to the area's art and suburban appeal. The facility, run by Audubon Florida, rehabilitates injured raptors including bald eagles, hawks, and owls, and features outdoor enclosures where visitors can view resident birds and learn about ongoing conservation work. It is one of the more unusual and education-focused stops in the Orlando suburbs and is well suited to travelers looking for something off the beaten theme-park path (Audubon Center for Birds of Prey).
Closer to the heart of the city, Lake Lily Park provides a relaxed public green space centered on its namesake lake, with paved walking paths, a playground, picnic areas, and a small community garden. It is a favorite local spot for a quiet morning stroll and offers a sense of Maitland's everyday residential rhythm. The park sits only a few minutes from downtown Maitland and pairs naturally with a stop at the nearby farmers market held on select weekends.
Of course, the biggest draw for many visitors is just down the road. From Maitland, the theme parks of the Walt Disney World Resort are roughly twenty-five to thirty minutes southwest, and Universal Orlando Resort is about twenty minutes south, placing the city within easy day-trip range of the most visited attractions in the United States (Walt Disney World).
Maitland's appeal as a short-term rental base comes from this balance: a peaceful, lake-lined community with its own cultural landmarks, walkable parks, and easy access to the surrounding Winter Park and Orlando area, all while remaining a comfortable retreat from the hustle of the theme-park districts to the south.
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