Has anyone bought a place in Orlando and wants to share their experience?

ChrisParker

DIS Veteran
Joined
Jun 17, 2011
We are investigating buying a place in Orlando to own as a short term rental until we can retire in 15 years and live there for six months less a day. (Which is about how long we had snow here this year...)

Has anyone here done that? I'm wondering if anyone has any advice about what to do or avoid. We're set up with Eric from Moving to the Magic and we've been looking at some MLS listings...

Thanks in advance! 🇨🇦:earsgirl:
 
Following as I've been wondering myself as a Canadian how hard it is to own the US, especially in the Orlando area.
 


My dentist owns in that area. He says the key to making it work is to have a good company that you trust to take care of your property. Then, make sure the people you hire are actually doing what they're supposed to do. Finding those reputable people is probably the hard part.
 
My dentist owns in that area. He says the key to making it work is to have a good company that you trust to take care of your property. Then, make sure the people you hire are actually doing what they're supposed to do. Finding those reputable people is probably the hard part.

Our friends have owned there for 17 years. They spend 6 weeks in spring and six weeks in the fall to enjoy but also do renovations for next years rentals. They also said a good management company who actually does the work they are supposed to do is key
 
Following as well. We were there in March and were blown away by how affordable places are there compared to the Toronto area.

Curious to see if short term renting is feasible with so many hotels already in the area. Like are people able to get occupancy 20% of the year? 50-90%?
 


I've been considering it for a while and I'm still considering it but getting more hesitant.

You can certainly get good occupancy but I have to wonder at the price; there's just so much competition for short term rentals. I also wonder about resale as there are so many new communities being built and they typically have nicer amenities than the older ones.

As far as buying, financing is a pain. It's a lot easier if you can buy cash (e.g. using HELOC from Canada). You can finance, particularly through Canadian Banks that have US operations (e.g. TD, BMO, etc) but it's still not easy. There's a tax implication of receiving rental income from US property but I believe as long at you do everything right (e.g. file "closer ties to Canada" form, it's mitigated. And there can be estate tax implication (although that's really only a factor for people who are very rich). Ownership structure is also something you should consider.

One key point is that I think it's important to consider why you are buying. If you are buying for future retirement, you might not want to buy in the same area that you would if you are buying for investment and short term rental. (E.g. I do think you can do okay with short term rental around Kissimmee. I think pretty much anywhere else in Florida, you're property will be vacant much of the year. But personally, if we retire to Florida, I probably don't want to retire to Kissimmee). Similarly you're motivation might be different. If you are buying for investment / short term rental, you likely want it to be cash positive. If you are buying for personal use, you might not care if you are losing money on it every year.
 
Following as well. We were there in March and were blown away by how affordable places are there compared to the Toronto area.

...

I certainly can't disagree that it's more affordable than Toronto but that doesn't mean it's a good investment. You can probably say that 99% of cities in the world are more affordable than Toronto. Other than Vancouver, every city in Canada is more affordable than Toronto and it's certainly a lot easier to invest within Canada.
 
One key point is that I think it's important to consider why you are buying. If you are buying for future retirement, you might not want to buy in the same area that you would if you are buying for investment and short term rental.

That's a very valid point. At first, I thought it would be nice to have an extra income with a rental until we are ready to retire (still over 10 years away). Now it seems like more than a headache than it's worth. Our focus now is finding an affordable place that is comfortable for us to live in a few months of the year. When prepping a property for rental, there's so much else to consider. Like the of rooms needed to accommodate a family, furnishings, proximity to the parks, etc. All of which won't that important to us when we retire. We just want the warm weather. ;)

There are certainly cheap ways to live down there a in Orlando or further away. A decent trailer home with enough room for 2 people looks to be about 60-90K USD, while a really nice 4 bdr rental property with amenities is 250-450K!
 
Our friends have owned there for 17 years. They spend 6 weeks in spring and six weeks in the fall to enjoy but also do renovations for next years rentals. They also said a good management company who actually does the work they are supposed to do is key

I just wanted to say, if someone turns him in he can be in big trouble. A Canadian can work on their own property in the US if they are the only occupants, but if they run it as a rental they are supposed to hire out any work done to US residents. Hopefully they never piss off any of their neighbours (don't want a disgruntled neighbour turning them in).
 
We purchased a condo in Kissimmee (5 miles west of Animal Kingdom) 6 years back. Resort Management was later taken over by Wyndham Vacation Rentals, however we've never had our unit in the rental program anyhow. It's primarily used by our family for a few weeks a year, with the occasional rental to acquaintances. Depending on where and what you purchase, monthly HOA alone, can be very high. Between HOA, Management fees, insurance, electricity and Property Taxes, you can easily be paying over $10,000 USD annually in certain areas/Resorts. Also, because we do rent occasionally, we're required to have a business license (renewed annually), have to pay State, Municipal and Tourist Tax, and we have to file US income tax each year (times two, as my wife and I are co-owners).

We purchased at a time the CND dollar was at par with US, and housing prices were still ridiculously low, so despite the declining CND dollar over the years, and the increase in HOA and other expences, we're still managing okay. We always have the option of putting our unit in the program, should the dollar plummet further. Occupancy rate is about 74% for our resort, which is good, however I've spoken with other owners who advise that both the wear and tear on their units, and limited return on investment at times (many Resorts will drop prices as low as $70 per night, even if the going rate is $175, just to fill the place), can be frustrating. There's also consideration of Capital Gain tax if and when you sell. Paying Capital Gains in the US, generally means you don't pay twice (in Canada), however if like us, you purchased when the CND dollar was worth more than USD, then sell when it sits at 73 cents, the Canadian tax grab will want their share of the difference. Just a few things to think about. I now have an accountant in Canada and Florida, something I didn't really consider before the purchase. This would have been necessary anyhow, as when you eventually do sell, you have to submit a US tax return for each year you owned the property.

I will say that the purchase was easy however, less complicated than buying in Canada. No lawyer involved, my real estate contact (also my property manager), walked me through it. Other than a 3-day trip to look over some Resorts, everything was done by email/fax (offers, counter-offers, purchase). I just retired in November so I have more freedom to come and go, however with my wife still working and a kid in high school, I still won't be spending months at a time at Disney. But it's been a great ride so far. And we've been Annual Pass holders for a few years now. One of the perks. Cheers!
 
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We purchased a condo in Kissimmee (5 miles west of Animal Kingdom) 6 years back. Resort Management was later taken over by Wyndham Vacation Rentals, however we've never had our unit in the rental program anyhow. It's primarily used by our family for a few weeks a year, with the occasional rental to acquaintances. Depending on where and what you purchase, monthly HOA alone, can be very high. Between HOA, Management fees, insurance, electricity and Property Taxes, you can easily be paying over $10,000 USD annually in certain areas/Resorts. Also, because we do rent occasionally, we're required to have a business license (renewed annually), have to pay State, Municipal and Tourist Tax, and we have to file US income tax each year (times two, as my wife and I are co-owners).

We purchased at a time the CND dollar was at par with US, and housing prices were still ridiculously low, so despite the declining CND dollar over the years, and the increase in HOA and other expences, we're still managing okay. We always have the option of putting our unit in the program, should the dollar plummet further. Occupancy rate is about 74% for our resort, which is good, however I've spoken with other owners who advise that both the wear and tear on their units, and limited return on investment at times (many Resorts will drop prices as low as $70 per night, even if the going rate is $175, just to fill the place), can be frustrating. There's also consideration of Capital Gain tax if and when you sell. Paying Capital Gains in the US, generally means you don't pay twice (in Canada), however if like us, you purchased when the CND dollar was worth more than USD, then sell when it sits at 73 cents, the Canadian tax grab will want their share of the difference. Just a few things to think about. I now have an accountant in Canada and Florida, something I didn't really consider before the purchase. This would have been necessary anyhow, as when you eventually do sell, you have to submit a US tax return for each year you owned the property.

I will say that the purchase was easy however, less complicated than buying in Canada. No lawyer involved, my real estate contact (also my property manager), walked me through it. Other than a 3-day trip to look over some Resorts, everything was done by email/fax (offers, counter-offers, purchase). I just retired in November so I have more freedom to come and go, however with my wife still working and a kid in high school, I still won't be spending months at a time at Disney. But it's been a great ride so far. And we've been Annual Pass holders for a few years now. One of the perks. Cheers!
Can you get out of paying US income tax claiming Closer Ties to Canada?
 
You should also note that, if you own real property in the US, you will have to have your will probated in the US when you die. That will take longer and you'll pay double the probate fees (Canada and the US).
 
Can you get out of paying US income tax claiming Closer Ties to Canada?
You have an option of not having to do a US return, but you give up 30% off the top. Considering our current PM has bungled relations with the US (and everyone else), I would not count on any leniency!
 
I think you are confused about who is the one bungling relations. Hint: it originates in the US.
Actually, it all began with our leader's snub. Now he's looking for favours. Fortunately, fingers-crossed, we can re-build relations in October.
 
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