Airbnb Management
Full-service Airbnb management for your short-term rental. Nationwide.
Wailea, Hawaii
Wailea, Hawaii, offers a diverse range of Airbnb accommodations that cater to various preferences and budgets. Guests can choose from luxurious oceanfront villas that provide stunning views of the Pacific and direct beach access, perfect for those seeking a high-end, private retreat. There are also upscale condos and apartments within resort communities, offering amenities like pools, golf courses, and spas, ideal for travelers looking for a blend of comfort and convenience. For a more intimate experience, visitors can opt for charming cottages or ohanas, which are smaller guesthouses that often feature lush garden settings and a more local feel. Additionally, there are budget-friendly options such as shared rooms or studios that still allow guests to enjoy the beauty of Wailea without breaking the bank. Each type of accommodation provides a unique way to experience the natural beauty and luxury of this Hawaiian paradise.
In Wailea, Hawaii, short-term vacation rentals, including Airbnbs, are subject to specific regulations and taxes. Maui County, which encompasses Wailea, 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 there are limits on the number of short-term rental homes allowed in certain areas to preserve neighborhood character. Additionally, property owners must pay the Transient Accommodations Tax (TAT) and the General Excise Tax (GET) on rental income. The TAT is a state tax applied to gross rental proceeds, while the GET is a tax on business activities in Hawaii. Compliance with these regulations and taxes is essential for operating a legal short-term rental in Wailea.
Managing an Airbnb in Wailea, Hawaii, involves several key tasks to ensure a successful operation. Hosts need to focus on maintaining the property to high standards, given the area's reputation for luxury and its appeal to tourists seeking a premium experience. This includes regular cleaning, timely maintenance, and ensuring all amenities are in excellent condition. Effective communication with guests is crucial, from the initial booking inquiry to post-stay follow-ups, to enhance guest satisfaction and encourage positive reviews. Additionally, managing bookings efficiently to maximize occupancy rates, setting competitive pricing based on seasonal demand, and adhering to local regulations and tax requirements are essential. Given Wailea's popularity, hosts should also consider implementing marketing strategies to stand out in a competitive market, such as professional photography and detailed, enticing property descriptions.
Wailea, Hawaii, is a luxurious resort community on the island of Maui, known for its stunning beaches, upscale amenities, and world-class golf courses. When choosing an Airbnb in Wailea, consider staying near Wailea Beach for easy access to its pristine sands and crystal-clear waters, perfect for sunbathing and snorkeling. The Wailea-Makena area offers a range of accommodations, from oceanfront condos to private villas, providing breathtaking views and a serene atmosphere. Staying near The Shops at Wailea is ideal for those who enjoy shopping and dining, with a variety of high-end boutiques and restaurants nearby. Additionally, the proximity to the Wailea Golf Club makes it a great choice for golf enthusiasts. Overall, Wailea offers a blend of relaxation and luxury, making it an excellent choice for a memorable Hawaiian getaway.
Wailea, Hawaii, is an attractive market for investing in an Airbnb 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 premium vacation experience ensures a steady demand for short-term rentals. Wailea's year-round warm climate and picturesque landscapes make it a popular choice for tourists, contributing to high occupancy rates and potentially lucrative rental income. Additionally, the limited availability of accommodations in this exclusive region can drive up nightly rates, offering investors the opportunity for significant returns. However, potential investors should be mindful of local regulations and the impact of tourism on the community to ensure a sustainable and compliant investment.
Wailea, Hawaii, is a popular destination for tourists seeking luxury and relaxation, which is reflected in the average Airbnb revenue for properties in the area. Hosts in Wailea typically benefit from high occupancy rates and premium pricing, especially during peak travel seasons such as winter and summer holidays. The average revenue for Airbnb listings in Wailea can vary significantly depending on factors such as property size, location, amenities, and the time of year. However, due to the area's appeal and the high demand for vacation rentals, many hosts in Wailea report strong earnings, often surpassing the average revenues seen in less tourist-centric locations. This makes Wailea an attractive market for Airbnb hosts looking to capitalize on the area's allure and the steady influx of visitors.
Wailea, Hawaii, is a popular destination for tourists, which significantly influences the occupancy rates and seasonality of Airbnbs in the area. The occupancy rate tends to be high throughout the year, with peak seasons typically occurring during the winter months, from December to March, when visitors seek to escape colder climates. Additionally, the summer months, particularly June through August, also see increased occupancy due to family vacations and favorable weather conditions. However, there may be a slight dip in occupancy during the shoulder seasons, such as late spring and early fall, when tourist activity is generally lower. Overall, Wailea's appeal as a luxury beach destination helps maintain relatively high occupancy rates year-round.
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.