Rent Your Vacation Home or Condo in Wailea, Hawaii

Positive vacation rental trends in Wailea, Hawaii when you considering renting out your Wailea home as a short-term rental. To reap the benefits of owning a vacation home, it’s important to consider your goals and needs. Not everyone wants to be a full-time homeowner and, like homeownership in general, there are pros and cons to renting out your home. But if you’re looking for something fun to do on your next trip, short-term rentals can be a great option. For example, if you’re planning an upcoming trip with friends or family who are looking for a cottage in Wailea, or want to rent out your condo while you’re away, look into vacation rentals in Wailea. You might find that the process is more straightforward and less expensive than purchasing a property, especially if you don’t need to make any major renovations. Plus, if you have kids who love the beach or want someplace to play board games during rainy days, you may also find that renting out your Wailea condo is an affordable option.

When partnering with RedAwning for your property management needs, we can make sure your Wailea rental is set up correctly and ready to generate the most amount of revenue possible per stay.

Current Vacation Rental Trends in Wailea

During the month of November, Kihei, for example, is projected to generate over $331/night for a 2 bedroom vacation rental, on average! There were 5,533 vacation active rental properties in Wailea.  5,486 are renting the entire place, and 47 are shared rooms.  On average, during the month of November 2023, each vacation rental property in Kihei is booked 81% of the time, and most hosts are projected to generate $5,652 or more during the month of November! Is your home in Wailea and areas including , Wailea, or another neighborhood in Wailea, Hawaii? See how much you could earn with your Wailea vacation rental.

$331.00 Per Night*


81% Occupied*


$5,652.00 Per Month*

* Based on the median average of all vacation rentals in the Wailea area.
Get a free estimate for your home or condo.

Featured Wailea Vacation Rental Generating Record Profits With RedAwning

Wailea Beach Villa B102 Starting at $3,363 to $7,241 per night!

Voted #3 Resort in Hawaii by Conde Nast Reader’s Choice Awards 2019! Welcome to the prestigious oceanfront Wailea Beach Villa B102. This 3 bedroom/3.5 bath is desirably located just steps from the adult infinity edge pool and stunning Wailea Beach. With breathtaking ocean views and close proximity to the beach, this beautifully designed beachfront villa is exactly what dream vacations are made of! Enticing,... Read More

This Wailea vacation home is presented on every travel website, where travelers are looking to book accommodations (Airbnb, VRBO, Expedia, Google Travel, and hundreds more). And, with RedAwning's dynamic pricing, daily rates are adjusted based on seasonality and demand in Wailea.

Successful short-term vacation rentals in Wailea, Hawaii

For decades, Wailea has been a popular vacation destination for those looking to relax and enjoy the white sand beaches, picturesque views, and world-class dining. With all this in mind, it’s no surprise that short-term rental properties are quite popular in Wailea. It’s important to keep in mind that short-term rental properties are not allowed in all Wailea neighborhoods. In order to ensure your property is well-situated for guests, it’s a good idea to talk to your local Wailea real estate agent before listing an available property as a short-term rental.

By renting out a vacation home in Wailea, you can earn an extra income while enjoying Hawaii’s idyllic surroundings. If you’re looking for ways to make money on the side, it’s easy to turn your home into a rental property. And unlike a standard rental, there are no broker fees or application fees. Plus, when you invest in real estate, you can earn tax write-offs and other perks. There are several benefits to renting out a vacation home in Wailea: You get to enjoy the seclusion of your tropical paradise. You get to save money by avoiding expensive hotel bills. You get to spend more time with family and friends because you don’t have to commute back and forth from your main residence. However, it’s important to remember that short-term rentals can be a controversial topic in Hawaii and could affect your chances of buying property in Wailea in the future.

RedAwning takes the guess-work out of Wailea property management, and we work with you to ensure your Wailea short-term rental is set up perfectly to attract guests and maximize your rental revenue, from day-one.

See how much your Wailea vacation rental could earn:

Revenue Projections for Vacation Rentals in Kihei/Wailea, Hawaii during December, 2023

Based on a 2 bedroom, which is the most common Wailea vacation rental home size, we've come up with an estimated rental amount you could charge per night and how much demand there is for each day in December. Higher bars below can command higher prices, if your Wailea vacation rental is available during these days.

Average Daily Price & Percent Occupied Next Month In Wailea

Note: These averages are based on a 2 bedroom home in Kihei. If you'd like to find out how much revenue your home could make by providing the number of bedrooms and specifics about your vacation rental, please try our  free vacation rental calculator and/or speak with one of our vacation rental experts about your vacation home, condo or unique vacation rental experience.

Interested in learning how you can maximize your vacation rental revenue in Wailea, Hawaii?

If you are a speculative home buyer or have another home in Hawaii, check out our other Hawaii Vacation Rental Management reports in HanaleiHauulaHonoluluKahukuKailua KonaKamuelaKaneoheKapaaKapoleiKiheiKilaueaKoloaLahainaLaieLihuePaiaPrincevilleWaianaeWaikoloaMauiKeaauAnaholaPahoaVolcanoHaenaHiloWailukuKaanapaliNapiliHanaKailuaKapaluaPepeekeoKahuluiWainihaKahanaPapaaloaKonaWaialuaKohala CoastKulaKeauhouMountain ViewHonokowaiHaleiwaPapaikouAniniKehena,  and Ele'Ele, Hawaii or view all of our vacation rental market reports

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