Airbnb Management
Full-service Airbnb management for your short-term rental. Nationwide.
Madison, Wisconsin
In Madison, Wisconsin, guests can choose from a diverse array of Airbnb accommodations that cater to various preferences and budgets. Options range from cozy private rooms in charming historic homes to entire apartments or houses that offer more space and privacy. Many listings highlight the city's unique character, with some properties featuring classic Midwestern architecture or modern, eco-friendly designs. For those seeking a more rustic experience, there are also cabins and cottages available, often located near the picturesque lakes or lush parks that Madison is known for. Additionally, some hosts offer unique stays such as converted barns or artistic lofts, providing a distinctive and memorable experience for visitors. Whether travelers are looking for a convenient downtown location or a tranquil retreat in the suburbs, Madison's Airbnb offerings provide a wide variety of choices to suit different tastes and needs.
In Madison, Wisconsin, short-term rentals like Airbnb are subject to specific regulations to ensure compliance with local laws. Hosts are required to obtain a Tourist Rooming House (TRH) license if they rent out their property for fewer than 29 consecutive days. Additionally, hosts must adhere to zoning regulations, which may restrict short-term rentals in certain residential areas. Madison also mandates that hosts collect and remit room taxes, which include a 10% local room tax and a 5.5% state sales tax on the rental income. These regulations aim to balance the interests of property owners, guests, and the local community while ensuring safety and accountability in the short-term rental market.
Managing an Airbnb in Madison, Wisconsin, involves several key tasks to ensure a successful operation. Hosts need to focus on maintaining the property to meet guest expectations, which includes regular cleaning, restocking essentials, and addressing any maintenance issues promptly. Effective communication with guests is crucial, from providing clear check-in instructions to being responsive to inquiries and concerns. Pricing strategies should be adjusted seasonally, considering local events like the University of Wisconsin-Madison's academic calendar and sports events, which can affect demand. Additionally, compliance with local regulations and taxes is essential, as Madison has specific short-term rental rules that hosts must follow. Marketing the property through appealing listings and leveraging positive reviews can also enhance visibility and attract more bookings.
Madison, Wisconsin, offers several vibrant neighborhoods ideal for an Airbnb stay, each with its unique charm. Downtown Madison is a prime choice, providing easy access to the State Capitol, the University of Wisconsin-Madison campus, and the bustling State Street, known for its eclectic mix of shops, restaurants, and cultural venues. The Near East Side, including the Atwood and Willy Street areas, is another popular option, celebrated for its bohemian vibe, local eateries, and community events. For a more tranquil experience, the Monroe Street area offers a quaint, residential feel with boutique shopping and proximity to the scenic Lake Wingra and the University Arboretum. Each of these neighborhoods provides a distinct taste of Madison's vibrant culture and welcoming atmosphere.
Madison, Wisconsin, presents a promising Airbnb investment opportunity due to its vibrant cultural scene, strong educational presence, and steady influx of visitors. Home to the University of Wisconsin-Madison, the city attracts a constant stream of students, faculty, and visiting families, ensuring a consistent demand for short-term rentals. Additionally, Madison's thriving arts and music festivals, such as the Wisconsin Film Festival and the Great Taste of the Midwest, draw tourists year-round. Neighborhoods like Capitol, State-Langdon, and Monroe Street are particularly appealing for investors due to their proximity to key attractions, dining, and entertainment options. The city's commitment to sustainability and outdoor activities, with its numerous parks and lakes, further enhances its appeal as a destination, making it a lucrative market for Airbnb investments.
As of the latest data, the average Airbnb revenue in Madison, Wisconsin, reflects a dynamic short-term rental market influenced by various factors such as location, seasonality, and property type. Hosts in Madison typically see fluctuations in their earnings, with peak revenues often occurring during the summer months and major local events, such as University of Wisconsin-Madison's graduation ceremonies and Badgers football games, which attract a significant number of visitors. On average, hosts can expect monthly revenues ranging from $1,500 to $3,000, depending on the property's proximity to downtown, amenities offered, and overall guest experience. The city's vibrant cultural scene and picturesque surroundings continue to make it an attractive destination for travelers, thereby sustaining a healthy demand for Airbnb accommodations.
Madison, Wisconsin, experiences a fluctuating Airbnb occupancy rate influenced by its distinct seasonal patterns. The city sees higher occupancy rates during the warmer months, particularly from May to October, when visitors are drawn to outdoor activities, local festivals, and the University of Wisconsin-Madison events. This period coincides with the peak tourist season, leading to increased demand for short-term rentals. Conversely, the colder months, especially from November to March, typically witness a decline in occupancy rates as the harsh winter weather deters some travelers. However, events like winter sports and holiday gatherings can still attract visitors, providing occasional boosts in occupancy during this off-peak season. Overall, Madison's Airbnb market is characterized by its seasonality, with occupancy rates peaking in the summer and dipping in the winter.
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.