Find Your Key West STR Realtor
Key West is America's southernmost island paradise, offering a unique blend of history, culture, and tropical beauty. Connect with realtors who specialize in Florida Keys vacation rental investments.
Get Matched with a Key West Expert
Why Invest in Key West STRs?
Key West offers some of the highest STR returns in Florida
5M+ Annual Visitors
Key West draws millions of visitors annually for its unique culture, sunset celebrations, and tropical island experience.
Premium Island Rates
Limited inventory and high demand create some of the highest nightly rates in Florida, especially for historic properties.
Scarcity-Driven Value
Limited buildable land on the island and strict development regulations create natural supply constraints and appreciation.
Year-Round Tropical Climate
Warm weather year-round means consistent rental demand without significant seasonal drops typical of northern destinations.
What a Key West STR Expert Brings
Local knowledge that makes the difference
- Historic Property Expertise - Understand Key West's historic district rules, renovation requirements, and transient license regulations
- Revenue Projections - Accurate income estimates based on actual Key West market data and seasonal patterns
- Location Analysis - Know which neighborhoods from Old Town to New Town command premium rates and attract ideal guests
- Local Vendor Network - Connections to island-based property managers, cleaners, and maintenance pros who understand tropical properties
- Regulatory Guidance - Navigate Key West's transient rental license system, HARC approvals, and Monroe County requirements
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Get Matched FreeFrequently Asked Questions
Common questions about STR investing in Key West
How does Key West's transient rental license system work?
Key West has a limited transient rental license pool that was capped in the 1990s. New licenses are extremely rare and valuable - licenses can transfer with property sales or may occasionally become available through the city. Properties must be in specific zoning districts to qualify. This scarcity makes licensed properties premium investments. Our agents can help identify properties with existing licenses.
What ROI can I expect from Key West vacation rentals?
Key West offers some of Florida's highest STR returns due to limited supply and premium demand. Properties average $385/night with 74% occupancy, generating $104,000+ in annual gross revenue. Historic properties in Old Town and waterfront locations command even higher rates. While entry prices are substantial ($800K-$2M+), the scarcity-driven market provides strong appreciation alongside rental income.
What are the best areas to invest in Key West STRs?
Old Town Key West commands the highest nightly rates with its historic charm, walkability to Duval Street, and proximity to attractions. Properties near Mallory Square and the Historic Seaport perform exceptionally well. New Town offers more affordable entry points but with lower nightly rates. Pool homes and properties with off-street parking are especially valuable given the island's constraints.
What special considerations apply to Key West historic properties?
Many Key West properties fall under Historic Architectural Review Commission (HARC) oversight. Exterior modifications require HARC approval, which can impact renovation timelines and costs. However, historic properties command premium rates from guests seeking authentic Key West experiences. Hurricane preparedness, flood insurance, and proper maintenance of older structures are essential considerations.
How does Key West seasonality affect rental income?
Key West's tropical climate creates more consistent year-round demand than mainland Florida. Peak season runs from December through April, with Fantasy Fest (October) and Pride (June) creating additional high-demand periods. Summer sees slightly lower rates but good occupancy. Unlike beach destinations that are highly seasonal, Key West's unique culture and events maintain strong occupancy throughout the year.
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