Airbnb Management
Full-service Airbnb management for your short-term rental. Nationwide.
Key West, Florida
In Key West, Florida, guests can choose from a diverse array of Airbnb accommodations that cater to various preferences and budgets. Options range from charming conch-style cottages and historic homes in Old Town, offering a taste of the island's rich history and vibrant architecture, to modern condos and luxury villas with stunning ocean views. For those seeking a more unique experience, there are houseboats and eco-friendly tiny homes that provide a closer connection to the natural beauty of the area. Many properties feature amenities such as private pools, lush tropical gardens, and easy access to the island's famous beaches and nightlife, ensuring a memorable stay in this tropical paradise.
In Key West, Florida, short-term rentals like Airbnb are subject to specific regulations to manage their impact on the community. The city requires hosts to obtain a business tax receipt and a special vacation rental license to operate legally. These licenses are typically limited to certain zoning districts, and there are restrictions on the number of times a property can be rented out per year, often capped at 25 times annually for less than 30 days each time. Additionally, hosts must comply with safety and noise regulations to ensure neighborhood harmony. Regarding taxes, Airbnb hosts in Key West are required to collect and remit a 5% tourist development tax and a 7.5% sales tax on their rental income. These taxes are crucial for funding local infrastructure and tourism-related services.
Managing an Airbnb in Key West, Florida, involves several key tasks to ensure a successful operation. First, property owners must focus on maintaining the property to meet the high expectations of guests, which includes regular cleaning, maintenance, and timely repairs, given the wear and tear from frequent visitors. Effective marketing is crucial, leveraging high-quality photos and detailed descriptions to highlight the unique features of the property and its proximity to popular attractions like Duval Street and the Ernest Hemingway Home. Pricing strategies should be dynamic, adjusting for peak tourist seasons and local events to maximize occupancy and revenue. Additionally, excellent customer service is essential, requiring prompt communication with guests before, during, and after their stay to address inquiries and resolve any issues. Compliance with local regulations and obtaining necessary permits is also critical to avoid fines and ensure smooth operations. Finally, gathering and responding to guest reviews can help improve the property's reputation and attract more bookings.
Key West, Florida, offers a variety of vibrant neighborhoods ideal for an Airbnb stay, each with its own unique charm. Old Town is a popular choice, known for its historic architecture, lively atmosphere, and proximity to attractions like Duval Street, where you can enjoy dining, shopping, and nightlife. The Truman Annex is another sought-after area, offering a quieter, more residential feel while still being close to the action, including the beautiful Fort Zachary Taylor State Park. For those seeking a more laid-back vibe, the Bahama Village neighborhood provides a rich cultural experience with its colorful streets and local eateries. Lastly, the Casa Marina area offers a more upscale experience, with easy access to beaches and luxury amenities. Each of these areas provides a distinct taste of Key West's unique island lifestyle.
Key West, Florida, is a highly attractive market for Airbnb investment due to its year-round tourism appeal, driven by its tropical climate, vibrant nightlife, and rich cultural history. The island city is renowned for its beautiful beaches, water sports, and historic sites like the Ernest Hemingway Home and Museum, drawing a diverse range of visitors. The high demand for short-term rentals is bolstered by limited hotel accommodations, allowing Airbnb hosts to capitalize on premium pricing, especially during peak seasons such as winter and spring. Additionally, Key West's walkability and unique charm make it a preferred destination for travelers seeking an authentic and immersive experience, further enhancing its potential as a lucrative Airbnb market. However, investors should be mindful of local regulations and the competitive landscape to ensure compliance and optimize their returns.
Key West, Florida, is a popular tourist destination known for its vibrant nightlife, historic sites, and beautiful beaches, which significantly influences the Airbnb market in the area. On average, Airbnb hosts in Key West can expect to earn a substantial income due to the high demand for short-term rentals, particularly during peak tourist seasons such as winter and spring. The average revenue for Airbnb properties in Key West varies depending on factors such as location, property size, and amenities offered, but hosts often see higher earnings compared to other regions due to the city's year-round appeal and premium rental rates. This consistent demand allows many hosts to maintain high occupancy rates, contributing to a lucrative market for short-term rental investments in Key West.
Key West, Florida, is a popular tourist destination with a high Airbnb occupancy rate, often exceeding 80% during peak seasons. The city's tropical climate and vibrant cultural scene attract visitors year-round, but occupancy rates typically peak during the winter months, from December to April, when tourists flock to escape colder climates. This period coincides with numerous local events and festivals, further boosting demand. Conversely, the summer months, particularly from June to September, see a slight dip in occupancy due to the hot, humid weather and the onset of hurricane season, although the rates remain relatively robust compared to other destinations. Overall, Key West's Airbnb market benefits from its perennial appeal, with only moderate fluctuations in occupancy throughout the year.
Why Choose Checkmate Rentals?
![]() | Other Property Managers | |
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Cost | Starting at 15% fee | 25-40% fee |
Guest Communications | Guest response within 10 minutes, 24 hours a day | Sporadic guest communications |
Host Communications | Designated host call in phone line | Bot response assistants |
Insurance | Full damage protection for every reservation | Unreliable insurance coverage |
Contract | No annual agreements | Contract lock-ins |
Checkmate Rentals

Attract Guests
List on top booking sites
Optimize listings for SEO
Feature show-stopping photos
Competitive, dynamic pricing
Mangage Operations
Tailored pricing algorithms
24/7 guest service
Reliable, professional cleaning
Restocking & inventory management
Maintenance coordination


Host Care
Unlimited owner stays
Flexible contract options
East to use host portal
Set it and forget it billing
Exclusive insurance discounts via our partner network
Get in touch with us.

Checkmate Rentals is a full-service property manager. That means the Airbnb listing, the home, the guest and the work is our responsibility.
Local Team Support
Know that you have a friendly, accessible team right up the road to handle any property needs.
Guest Screenings
Book only the most qualified guests 25 and over who’ll enjoy your home the right way.
Unlimited Owner Use
Block off your vacation days with ease, and enjoy your home as often as you want.
Reliable Property Maintenance
Keep your home running smoothly around the clock with a fast, reliable maintenance team.
Transparent Finances
Transparent Finances Booking payouts get paid directly to you for full financial transparency. We never handle your money.
Fast 24/7 Guest Communication
Make every guest feel cared for with industry best response times of 1-15 minutes day and night.
Marketing
Target, attract & book qualified guests with photography, email marketing, and optimized listings.
Revenue Management
Get the competitive edge with dynamic pricing and rates optimized daily by your pricing manager.

Ready to make the jump?
Let's get started! Schedule a call today to learn more about Checkmate Rentals.