Airbnb Management
Full-service Airbnb management for your short-term rental. Nationwide.
Wailea, Maui, Hawaii
In Wailea, Maui, Hawaii, guests can choose from a variety of Airbnb accommodations that cater to diverse preferences and budgets. The area is renowned for its luxury resorts and stunning beaches, and this is reflected in the Airbnb offerings. Visitors can find upscale oceanfront villas and condos that provide breathtaking views of the Pacific Ocean, often featuring amenities such as private pools, hot tubs, and direct beach access. For those seeking a more intimate experience, there are charming cottages and bungalows nestled in lush tropical gardens, offering a serene retreat. Additionally, there are modern apartments and studios that provide a more budget-friendly option while still being conveniently located near Wailea's shopping centers, golf courses, and dining establishments. Whether travelers are looking for opulence or a cozy hideaway, Wailea's Airbnb options offer something for everyone.
In Wailea, Maui, Hawaii, short-term rentals, including Airbnbs, are subject to specific regulations to manage their impact on the community and housing market. These rentals must be located in areas zoned for hotel use or in designated short-term rental districts. Property owners are required to obtain a short-term rental home permit, which involves notifying neighbors and adhering to occupancy limits and noise regulations. Additionally, there is a Transient Accommodations Tax (TAT) and a General Excise Tax (GET) that hosts must collect from guests and remit to the state. The TAT is currently set at 10.25%, while the GET is 4%, with an additional county surcharge that may apply. Compliance with these regulations and taxes is crucial for operating legally in Wailea.
Managing an Airbnb in Wailea, Maui, Hawaii, involves several key responsibilities to ensure a successful operation. Hosts must focus on maintaining the property to high standards, given the area's reputation for luxury and natural beauty. This includes regular cleaning, landscaping, and timely repairs to preserve the appeal of the property. Effective guest communication is crucial, from prompt responses to inquiries and booking confirmations to providing detailed check-in instructions and local recommendations. Additionally, compliance with local regulations and tax requirements is essential, as Maui has specific short-term rental laws. Marketing the property effectively through high-quality photos and engaging descriptions can help attract guests, while dynamic pricing strategies can optimize occupancy and revenue, especially during peak tourist seasons.
Wailea, located on the southwestern coast of Maui, Hawaii, is a premier destination for those seeking a luxurious and tranquil getaway. Known for its stunning beaches, upscale resorts, and world-class golf courses, Wailea offers a perfect blend of relaxation and adventure. Staying in an Airbnb here provides access to pristine beaches like Wailea Beach and Makena Beach, where you can enjoy sunbathing, snorkeling, and breathtaking sunsets. The area is also home to the Shops at Wailea, offering high-end shopping and dining experiences. With its lush landscapes and proximity to natural attractions like the Ahihi-Kinau Natural Area Reserve, Wailea is an ideal spot for travelers looking to experience the beauty and serenity of Maui.
Wailea, located on the picturesque island of Maui in Hawaii, is a prime market for investing in Airbnb properties due to its reputation as a luxury destination with stunning beaches, world-class golf courses, and high-end resorts. The area's appeal to affluent travelers seeking a serene and upscale vacation experience makes it an attractive spot for short-term rentals. Wailea's consistent influx of tourists, drawn by its natural beauty and cultural attractions, ensures a steady demand for accommodations. Additionally, the region's relatively high average daily rates and occupancy levels contribute to potentially lucrative returns for Airbnb investors. However, it's crucial to stay informed about local regulations and community sentiments regarding short-term rentals to ensure compliance and sustainability in this competitive market.
Wailea, located on the island of Maui in Hawaii, is known for its luxury resorts, stunning beaches, and high-end amenities, making it a popular destination for tourists seeking a premium vacation experience. The average Airbnb revenue in Wailea tends to be higher compared to other regions, primarily due to its upscale market and the high demand for vacation rentals in this picturesque locale. Properties in Wailea often command premium prices, with many offering ocean views, proximity to golf courses, and access to exclusive beach areas. Consequently, hosts in Wailea can expect substantial earnings, particularly during peak tourist seasons, when the influx of visitors seeking luxury accommodations is at its highest. However, it's important to note that revenue can fluctuate based on factors such as seasonality, property type, and specific location within Wailea.
Wailea, located on the island of Maui in Hawaii, typically experiences high occupancy rates for Airbnb properties, driven by its reputation as a luxury destination with stunning beaches and upscale amenities. The occupancy rate tends to peak during the winter months, from December to March, when tourists flock to escape colder climates, and again in the summer months, particularly June through August, when families take advantage of school vacations. Shoulder seasons, such as late spring and early fall, may see a slight dip in occupancy, but Wailea's consistent appeal as a year-round tropical paradise helps maintain relatively stable demand throughout the year. Special events, holidays, and the region's natural beauty further contribute to its attractiveness, ensuring that Airbnb properties in Wailea remain a popular choice for travelers seeking a premium Hawaiian experience.
Why Choose Checkmate Rentals?
![]() | Other Property Managers | |
---|---|---|
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.