Nick Halverson, Founder, Owner and CEO, Osa Property Management

I’m Nicholas Halverson, and I am the founder and owner of Osa Property Management.

We’re a full-service vacation rental property management company in Costa Rica. We were officially founded around 2017, although I’ve been managing properties in Costa Rica since 2009. I just kind of put a name to it then.

We operate from a geographic standpoint in the Central Pacific down to the Panama border, and we’re starting to move inland a little bit. We’ve stayed away from the northern Guanacaste area for now, just because it’s outside our current footprint. Anytime we grow, there’s a strategy behind it, unless there’s a compelling reason to jump across regions.

On the rental side, we handle all the accounts on the platforms — Airbnb and Vrbo. We were one of the first property management companies that Marriott chose to work with in Costa Rica through the Marriott Homes & Villas program, going on about five years ago. We handle all guest communications and all taxes — we handle everything from that standpoint. Our owners really don’t have to worry about anything, including recommendations and things like that. We’ve had owners who haven’t been to their property in six years, which is kind of the extreme case of where we truly handle everything.

We schedule and work with pool cleaners, landscapers and everything else, making sure they’re not interrupting guests. We don’t actually perform those services ourselves, but we outsource them. We handle all bill pay and make sure all of them are paid, and all taxes are covered. From an owner standpoint, we keep them tax compliant with corporation requirements and registration that has to take place every year. We’ve started to offer that service through a lawyer we work with, who will soon be in-house.

From a guest standpoint, we offer seven-day-a-week guest relations for anything not broken in the house, and we have a separate team that handles concierge services — whether that’s a dinner reservation for four at a restaurant or private transportation from A to B. We have teams working seven days a week.

On top of that, we have a full team of cleaners and maintenance employees — all our own people. That has allowed us to grow in the right way because there’s accountability within our own team. Getting cleaners there and making sure they clean properly are critical success factors. We have SOPs in place so that when a house is cleaned, there’s a checklist that those cleaners must complete to make sure the property is properly handled. That checklist is actually shared with the owner if they want to see it, so everything is transparent — they know the property was cleaned, and they have access to the before-and-after photos. This gives them peace of mind, and sometimes it also protects against a negative feedback. If we get a four out of five on a cleaning score on Airbnb, we can show the owner the comparison against the 30 previous cleanings. Sometimes guests just don’t want to give you a five.

Personally, I have over 20 years in Costa Rica — buying, selling and managing real estate. I’ve been a permanent resident for over 10 years. I recently married a Costa Rican woman who is actually our general manager — she’s employee No. 1. She and I have built this company from the ground up. I built the first website, was doing the accounting, and was handling all the guest communications. She was cleaning the houses and making sure maintenance was there. We’ve truly touched every element of a property management business in Costa Rica.

Because of that experience, I understand the challenges of owning real estate in Costa Rica. I can see through the eyes of an expat — I understand the pain points, such as if a project was done. I sent money; was the work completed? Because I had the same problems before I had my own crew. I would send money down and show up three weeks later to find nothing had started. So for us, when we say an air conditioner is broken and we’ll get it fixed by four o’clock today, it gets fixed — and we provide that transparency to the owner, confirming it was indeed taken care of.

We have been focused on taking care of the owner and the guests at the highest possible quality level. In fact, we used to do landscaping. I had employees doing landscaping and cleaning pools. It proved to me that we weren’t good at it, and it can be very expensive if you don’t do it right.

Those experiences of trying to do everything and learning what we’re really good at and what we’re not so good at have allowed us to focus. We don’t waste time chasing ideas that don’t fit. In the last two to three years, we’ve really focused on quality properties. Over the weekend, I turned down three properties when someone sent me a note asking if we wanted to manage them. Six or seven years ago, I might have said yes. When you’re trying to grow, you pick up any property. We’re not doing that anymore. We could be double or three times the size if we were not discerning about the properties we choose.

In addition to that, we’ve become much more discerning about owners as well. When we’re speaking with potential owners in the marketplace who are interested in having us manage their home, they might have a beautiful home, but instinct tells us it may not be a good fit for us — whether that’s due to personality, experience or a lack of financial readiness. It sounds funny, but someone who has spent a million dollars on a house and then gets nervous about a $32 invoice for a project is something we try to identify and weed out early on.

There’s a kind of mating process that takes between three to six weeks. During that process, sometimes we’ll just say that we are not a good fit. It’s not personal — well, it kind of is, but because of that, our retention rate is really high, and we have less conflict once we start managing a house, because we try to set those expectations up front.

What we realized was that while we were growing, we were spending time and energy on less-than-ideal owners and homes. We said, What if we got rid of those bad fits? Doing so has actually allowed us to improve our processes in-house. Every month, our foundation is even stronger. We’re still growing, but our foundation is getting better and more robust. We’re getting ready to make some internal staffing changes because of that, as we onboard more technologies and solutions.

If you’re always chasing every home, you’re going to end up collapsing at some point. We think we have it figured out. We’re comfortable in what we’re doing, but we can always improve. I encourage our employees that if you’ve got a better idea, let us know, and let’s try it. If you’re going to propose something, let’s really vet it.

We also learned hard lessons. For example, we spent about five months on a technology transition and got two weeks before launch date before figuring out that we weren’t being told the truth by the vendor. The easy thing would have been to just keep going, but we pulled back. All five of us on that team felt misled, and that’s not a good partner for us. There’s a time when you have to admit a bad decision and move on.

One of our key differentiators is that we are a legally and fully compliant operating property management company in just about every market we operate in. That should be fundamental, but it isn’t for many of our competitors. A lot of people — especially expats who come down and decide to open a company — do it entirely online. In Costa Rica, you cannot have a service like ours exclusively online. You have to have a physical office. All employees must receive medical benefits and Christmas bonuses by law. It’s very expensive because we have 40 employees. There are also some cultural dynamics at play where an expat owner might gravitate toward a competitor who speaks their language, but we are insistent that everything we do is a hundred percent tax-compliant.

We are fully compliant with SUGEF, which is Costa Rica’s anti-money laundering requirement for all property management companies. We’ve been insistent on that from day one. There are serious compliance costs related to it, and our owners rarely ask about it, but it’s something I’ve insisted on. I sleep well at night knowing we’re doing everything we can to stay compliant.

Related to that, we have accounting in-house. All of the money coming in and all of our transactions with the banks we operate with are handled internally. Our accountants have exclusive access to those platforms. We’re compliant with the tax authorities and money laundering regulations — and most of our competitors aren’t. We receive calls every year from property owners who’ve had a property manager steal $10,000 from them. When I ask who they were working with, they’ll name a company I know isn’t operating legally. The response is usually, “Yeah, but they were cheaper.”

We also have bank accounts in both the United States and Costa Rica, with multiple banks within Costa Rica — credit cards with one, payroll with another. That spreads our risk and helps us ensure we’re getting the best service. Our cleaning maintenance and administrative teams are all in-house, which gives us the ability to set SOPs and processes to make sure all of our owners and guests are receiving the best quality service.

We’ve also been able to grow because of dynamic pricing. We work with a revenue management company on an exclusive basis — he works with clients around the world, but I negotiated a contract where he works exclusively with us in Costa Rica. He has about a decade of experience in analytics within the short-term rental and hospitality space.

We’ve also been recognized by Airbnb — not just as a super host, but we were invited as a top 150 property management company to their Host Summit in Mexico City in October 2025. That’s the top 150 property management companies across the Caribbean, Mexico and Central America. We are the only one in our region — there were four total in all of Costa Rica, three in Guanacaste in the North, and us covering from Jaco all the way South. Marriott has also highlighted us on their LinkedIn profiles for Homes & Villas by Marriott Bonvoy, and we’ve been featured on a webinar with Marriott.

I personally have over 20 years of experience in this space and in the markets we operate in, so I can relate to expat owners. I remember how different this was in 2005, and I’ll be celebrating 21 years in Costa Rica this March. I’ve experienced the ups and downs and the changes in the short-term rental market. It’s very different now than it was before COVID.

Related to our commitment to always improving, we invest heavily in continuing education. Several of our employees are taking college classes and technical classes. Two of our maintenance guys are currently working toward becoming certified electricians, and I’m paying for their time, transportation, classes and materials. It’s important for us to provide the best service and to provide the lifestyle that I think our workers deserve. If you work hard and want more, we’ll help make that happen.

For our own professional development, we’ve attended the Vacation Rental Management Association (VRMA) international conference for the last five years, and I’ve been a speaker at two of them. We’ve also attended conferences for short-term rentals. We’re always going to see where the industry is headed and learning from companies that are much bigger than us. My mentor manages around 800 very high-end homes in Vail and Beaver Creek, Colorado. I’m always benchmarking against bigger, more successful companies to make sure we’re doing everything we can as we grow. It’s that hunger to constantly learn, and those are the people we hire.

We’ve also learned that when someone comes on board with us, we don’t just tell them what to do. We have our processes, but if you have an idea you think we should be implementing, you have the freedom to propose it.

We’re also deeply committed to the community. Abigail Vargas, my general manager and wife, sits on several community boards related to tourism. This past December, Osa Property Management was awarded Company of the Year by CATUOSA, which is a tourism association tied into the ICT tourism board, encompassing hotels, tour operators and us. We’re also part of AmCham, the American Chamber of Commerce. Being connected to those local communities is critically important to us, and most of our competitors don’t do that. They simply ignore the local market. Since every one of our employees lives and works in basically the community they grew up in, we need to make sure we’re giving back as well.

We recently opened in Golfito, which is near the Panama border. We were actually approached by the Golfito Tourism Board through Abigail, who sits on a tourism association with them, and they said they needed more professional services as Golfito is expanding and elevating. They offered us free office space if we’d come employ people and work in their market, and we agreed.

We will be opening an office in San Isidro, Pérez Zeledón, in the next 90 days. We’ve already got the location picked out and have a couple of homeowners we’re currently in conversations with who will hopefully sign on. That will extend our coverage from Jaco, Tárcoles and to the north, all the way down through Uvita, Matapalo, Manuel Antonio, Dominical, Ojochal, San Buenos and Golfito, and then inland to San Isidro. There’s a Highway 243 from Dominical to San Isidro — about a 40-minute drive — that will push us inland, where there are some beautiful homes with mountain views and even some ocean views.

We also recently opened in Jaco in 2025. Jaco has thousands of condos, and we saw that as a real opportunity. Condos are a lot easier to manage than large homes. We currently manage several condos there.

We will also be announcing a partnership with a development as the exclusive vacation rental partner for a project called VS San Buenos, which will be launching by June. We’re going to be the exclusive vacation rental provider for any homeowner in that development, which ensures consistency of service, security and the best quality we can provide.

I did want to address something about our EcoSense program, since it came up. We have seven-day-a-week guest services for things like clogged toilets or Wi-Fi issues — that’s one team. We have another team for concierge — dinner reservations, horseback riding and so on. Then EcoSense is actually tied to our air conditioning units. If a door is open, the AC units will shut off. That’s part of our sustainability plan — trying to eliminate waste wherever we can. Guests will otherwise turn on the AC, leave for 12 hours, come back, and the AC has been running the whole time. That’s not only wasteful from an energy standpoint, it also wears down the AC unit.

We extend our sustainability commitment all the way down to the soaps, shampoos and cleaning products we provide. They are all environmentally safe and pet-friendly. We work closely with a manufacturer out of San José who provides us quarterly training and is available any time we have a question to make sure we’re using the right amount and type of product for each situation. We’ve also removed bleach from our homes entirely, so guests don’t even have access to bleach. That’s kind of the extreme end of what we do.

One other thing we’re doing that nobody else is doing is that I was the first person in Costa Rica to complete what’s called the Breezeway Safety Exercise. Breezeway, a property safety company, has inspected our properties twice, and their head of safety has trained our employees. I was the first person in Costa Rica to be certified as a short-term rental safety inspector. We have non-negotiables with our owners. Fire extinguishers, smoke detectors and carbon monoxide detectors are required. We’ll help facilitate getting those in place, but we make sure they’re there. It’s another way we’ve stood out.

Another way we differentiate is through our standard operating procedures around linens. We standardize our towels, sheets and blankets across all properties to ensure guests get a consistently great quality experience, whether they’re renting a large home or a one-bedroom condo.

For your audience who currently owns a property in Costa Rica as a second, third or fourth home, we would love to offer you a no-obligation, no-cost proposal and revenue projections. If you’re looking to purchase in Costa Rica, although we don’t handle real estate sales, we can provide an analysis of what a home would be able to rent for and what the expected revenue generation would be. Every home we manage has a full onboarding strategy behind it. In reality, it’s about a three-year plan, and we break that down for homeowners to show what to expect in year one, two and three. We guide you through that process so you can just come down, use your house, and enjoy it. That’s the whole idea of owning in Costa Rica — not to work. Let us do the work. Come down and enjoy your property anytime you want.

I just want to make sure I mentioned our owner transparency tools. Our owners have 24/7 access to their reservation calendar, accounting, and operational, maintenance or repair records. That’s how we’ve built trust with our owners. They can check in anytime with the information we’re sharing with them. They don’t have to send us an email and ask for last month’s report. It’s already in their owner portal in the cloud. That’s providing the kind of trust that only comes when information is always available and current.