Patience can pay.

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In 2011 I took a vacation to Hawaii for the first time. The trip was something I promised my grandmother, who passed 5 months earlier I would do. I rented a condo from a woman who happened to be a real estate agent. After chatting for a bit, I asked if there were any good deals around. She asked a few questions and said she would get back to me. I knew nothing about real estate. I still lived in an apartment at 31. We found something I thought could work after running some numbers. Made an offer that was countered, and I thought it was still to much, especially considering the economic conditions at the time. I walked away, a few days later a unit came on the market in the same condo complex for 25k less. I made an offer and it was accepted the same afternoon. Today I still own it, and my agent manages it for me. It's been a great investment and good learning experience. It hasn't been perfect or easy, but worth it. Anyone else own vacation rentals? How do you advertise? Have have you learned? What would you do different now?

[Garry C.]

Hey Tom,

I'm also in Colorado, Littleton, and I do vacation rentals. Well, rental. Hoping to turn that into rentalS soon. My story sounds similar to yours, except that I did mine in the cold climate, the Winter Park, CO area. Obviously I'm busy in the winter, due to ski season, but also in the summer, as WP is the 'Mountain Bike Capitol of the World', according to some.

I advertise on VRBO.com, and I have my own web site (http://sasquatch.rentals) and social media pages too. At first I tried many of the different rental sites, AirBNB, etc. But I found that I got a different class of people from those sites. VRBO users always treat my property well, which is not the case with many people from other sites. After one season I dropped from all the other listing sites and stuck with VRBO only. Although I am now back on AirBNB just because of the popularity of the site. We'll see if I stick with it or not, time will tell.
The biggest lesson I learned in that arena is that if someone starts off conversations by asking for a discounted rate, I don't want to rent to them even at my full rate. I usually tell these folks that we're booked, but thanks for considering us. Three times I've rented to folks that asked for discounts in the first or second correspondence, and they were the only three that did any damage to the property.

If your agent manages it for you, that's great. I asked my agent for a housekeeping referral and she hooked me up with a great person that cleans between stays whenever I need it. I also have a cleaning company that I use as a backup. That's the extend of my outside management. I do the rest myself, the listing sites make it easy to setup templates for email, take payments, etc.

A few things I've learned, or wish I had done sooner...
erentallock.com - There are others, but that's the one I use. Never have to deal with a key locked inside the unit again. That happened twice in one month and that was enough. Not only is it a pain for me, but the guests enjoy their vacation less when they have an issue like that.

Setup an LLC and bank account sooner. Mixing my rental income directly with my personal finances made it hard to keep track of and easy to overspend.

Cultivate great reviews. Every time I refund a security deposit I ask for a 'great review' telling us what they liked, and/or a direct email to me if there is anything that needs improvement. I'm over thirty five star reviews now, and have only one that's 4 stars. This can really help to set you apart from the competition.

I think that's enough for now. But if you have any specific questions, please feel free to reach out. I've been doing this for about two years now, successfully, and while I might not call myself an expert, I've learned a lot.