Airbnb Management
Full-service Airbnb management for your short-term rental. Nationwide.
Wailea-Makena, Hawaii
In Wailea-Makena, 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 more budget-friendly options, including shared spaces and private rooms in local homes, allowing guests to experience the island's hospitality firsthand. Whether travelers are looking for a lavish getaway or a cozy hideaway, Wailea-Makena's Airbnb options provide a range of choices to suit different tastes and needs.
In Wailea-Makena, Hawaii, short-term vacation rentals, including Airbnbs, are subject to specific regulations and taxes. The County of Maui, which encompasses Wailea-Makena, requires that short-term rental properties obtain a permit if they are rented for periods of less than 180 days. These permits are subject to zoning restrictions and caps on the number of permits issued in certain areas to manage the impact on residential neighborhoods. Additionally, operators must comply with safety and health standards and provide contact information for a local representative. In terms of taxes, Airbnb hosts in Wailea-Makena are required to collect and remit the Transient Accommodations Tax (TAT) and the General Excise Tax (GET) on their rental income. These taxes are crucial for compliance and contribute to the local economy by supporting infrastructure and public services.
Managing an Airbnb in Wailea-Makena, Hawaii, involves several key responsibilities to ensure a successful and smooth operation. Hosts need to focus on maintaining the property to high standards, given the area's reputation for luxury and natural beauty. This includes regular cleaning, landscaping, and addressing any maintenance issues promptly. Effective communication with guests is crucial, from the initial booking inquiry to post-stay follow-ups, ensuring a personalized and welcoming experience. Additionally, managing bookings to optimize occupancy rates while adhering to local regulations and tax requirements is essential. Marketing the property through appealing listings and leveraging social media can help attract more guests. Finally, staying informed about local events and attractions can enhance guest experiences and encourage positive reviews.
Wailea-Makena, located on the southwestern coast of Maui, Hawaii, is a prime destination for those seeking a luxurious and tranquil getaway. This area is renowned for its stunning beaches, including Wailea Beach and Makena Beach, which offer pristine sands and crystal-clear waters perfect for swimming, snorkeling, and sunbathing. Staying in an Airbnb here provides access to world-class golf courses, upscale shopping at The Shops at Wailea, and exquisite dining options that highlight local Hawaiian cuisine. The region is also known for its breathtaking sunsets and proximity to natural attractions like the Ahihi-Kinau Natural Area Reserve, making it an ideal spot for nature lovers and adventure seekers. Whether you're looking for a romantic retreat or a family-friendly vacation, Wailea-Makena offers a serene and picturesque setting with a touch of luxury.
Wailea-Makena, Hawaii, is an exceptional market for investing in Airbnb properties due to its stunning natural beauty, luxury appeal, and strong tourism demand. This area is renowned for its pristine beaches, world-class golf courses, and upscale resorts, attracting a steady stream of affluent visitors seeking a high-end vacation experience. The region's tropical climate and picturesque landscapes make it a year-round destination, ensuring consistent occupancy rates. Additionally, Wailea-Makena's proximity to popular attractions like the Road to Hana and Haleakalā National Park enhances its appeal to tourists. Investors can capitalize on the area's premium rental rates and the growing trend of travelers seeking unique, home-like accommodations, making it a lucrative market for short-term rental investments.
Wailea-Makena, Hawaii, is a popular destination for Airbnb rentals, attracting visitors with its stunning beaches, luxury resorts, and vibrant local culture. The average Airbnb revenue in this area tends to be relatively high compared to other locations, primarily due to its appeal as a premium vacation spot. Hosts in Wailea-Makena can expect to earn substantial income, especially during peak tourist seasons, such as winter and summer months, when demand surges. The combination of high nightly rates and strong occupancy levels contributes to the robust revenue potential for Airbnb properties in this region. However, it's important to note that revenue can vary significantly based on factors such as property size, amenities, location, and the overall market dynamics at any given time.
Wailea-Makena, Hawaii, experiences a relatively high occupancy rate for Airbnbs, driven by its appeal as a luxury destination with stunning beaches and upscale amenities. The occupancy tends to peak during the winter months, particularly from December to March, when tourists flock to escape colder climates and enjoy the warm, tropical weather. Additionally, summer months, especially June through August, also see increased occupancy due to family vacations and favorable weather conditions. However, there is a slight dip in occupancy during the shoulder seasons of spring and fall, when fewer tourists visit, leading to more competitive pricing and availability. Overall, the area's natural beauty and resort-like atmosphere contribute to a consistently strong demand for short-term rentals 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.