Investing in a Gateway Market for Vacation Rentals

You may not be aware of the term “gateway markets,” but if you are considering beginning a new vacation rental business or expanding an existing one, you should learn more about it!

Cities around North America are witnessing a real estate boom. Commercial, retail, and vacation rental properties are being purchased left and right. Patterns have arisen among this buying boom, and they are centered in what the industry refers to as ‘gateway markets.’

What exactly is a Gateway Market?

To understand why gateway markets are so crucial for real estate investment, we must first grasp the criteria that support the concept of a gateway market. The definition of a gateway market varies depending on who you ask, but the common opinion is that the word refers to a market that is highly investable. Of course, there are more specific traits, but this is a broad definition.

Other qualities, according to Sonny Kalsi’s website, include:

  • These markets have a high level of liquidity, which implies that real estate may be quickly bought and sold. In other words, gateway markets are usually popular with investors.
  • Gateway markets are typically well-known cities, such as New York and Los Angeles.
  • These marketplaces frequently wield social, economic, and political power.

What Are the Benefits of Investing in a Gateway Market?

The qualities of gateway markets are precisely what make them so appealing to investors. These markets are appealing to anyone other than real estate investors. They often have very high population densities and are frequently quite crowded tourist destinations.

Popular marketplaces offer the possibility to generate a lot of money in the short-term rental market. Regrettably, they also come with an unusually high level of competition. But there are things you can do to increase your chances of getting as many bookings as possible.

High levels of liquidity characterize gateway markets, but what does this mean? According to Wikipedia, market liquidity is “a market feature in which a person or corporation can quickly purchase or sell an asset without triggering a significant shift in the asset’s price.”

According to, gateway market investing requires “an experienced investor to know which markets to target, what projects to create, and how to serve the community in a profitable and successful manner.” Before investing in a gateway city, speak with a local real estate agent or reach out to the area’s gateway city council to learn more about the real estate prices, neighborhood needs, and potential.”

What Are the Most Important Gateway Markets in the United States?

  • Massachusetts’s Boston

For real-estate investors, Boston is an excellent choice. There are no substantial limitations on short-term rentals in the city, however hosts who rent for less than 28 days must register. According to our Markets page, the average daily rate in Boston is $153, and the most typical Length of Stay durations are 30+ nights (31%), and 2 nights (21%). (26 percent ).

  • Illinois, Chicago

The average daily rate in Chicago is slightly lower than in Boston, at $102. The total number of postings in Chicago (at the time of writing) is 3,555, with 1,751 of those listings categorised as one-bedroom listings. Remember that we only look at ‘entire property’ listings.

Malibu (California)

Malibu is well-known for its beaches, sunshine, and picturesque coastline. While the majority of Los Angeles has severe Airbnb regulations, the Malibu City Council allows short-term rentals as long as hosts register their STR company.

  • Tennessee (Nashville)

Nashville is a well-known tourist destination that draws tens of thousands of people each year. The average daily rate in Nashville at the time of writing this feature is $234, with a market occupancy percentage of 55%. Friday and Saturday are the busiest days, and hosts in the neighborhood charge more for both nights. With a 49 percent majority, the average minimum night stay requirement is two nights.

  • Louisiana’s New Orleans

New Orleans, another historic city, may be more seasonal than Nashville, but it also has some amazing investment numbers. With an average daily fee of $185, the occupancy rate is 63 percent. A majority of listings (41%) require a two-night stay minimum, and prices rise on Thursday, Friday, and Saturday nights because these are the most popular.

What Are Canada’s Major Gateway Markets?

  • British Columbia, Whistler

Whistler is one of Canada’s most well-known tourist destinations. It features one of the largest ski resorts in North America and has long been a popular winter vacation for both Canadians and Americans. Whistler is an excellent investment opportunity. According to our Markets page, Whistler now has a 63 percent occupancy rate and an average daily rate of $403. Friday and Saturday nights are the most popular — and most expensive. Whisler’s minimum night stay restrictions are split fairly evenly between 2 and 3 nights.

  • Montréal (Québec)

Both of Canada’s largest cities, Toronto and Vancouver, have limits on Airbnb rentals. Montréal, however, does not. According to, 19 million passengers passed through Montréal-Trudeau Airport in 2018. Of course, the pandemic had a significant impact, but in general, Montréal has a consistent high number of visitors. In Montréal, we tracked 4,449 active vacation rental properties, with 2,363 of them being one-bedroom listings. The average daily fee is $104, with a 44 percent occupancy rate. The market’s minimum night stay requirements are divided into 1, 2, and 30+ nights, with 26%, 26%, and 25%, respectively.

  • Québec (Québec)

As observed in Montréal, there are no limits on short-term rentals in Québec City. It receives approximately 4,000,000 visitors each year, and the vacation rental sector profits from this regular influx of travelers. The average daily fee is $148, with a 44 percent occupancy rate. The majority of hosts in the area have chosen not to impose a minimum night stay requirement.

How Can DPGO Assist?

As the year progresses, we will continue to update our list of gateway cities. Things change quickly in the data game, which is why dynamic pricing from DPGO will keep you competitive 24 hours a day, 365 days a year. All we require is your Airbnb listing URL to study your local market, and once we’ve made our recommendations, you can examine them and select how you want your dynamic pricing system to work!

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