Prospecting Vacation and Second Home Owners For Real Estate Listings!

My wife and I owned two vacation properties up in the mountains for 12 years. We rented them as both vacation rentals and long term rentals. One of them was a long term rental for several years, the other was mainly a vacation rental.

We know what it’s like to deal with vacationers, tenants, house cleaners, contractors, handymen, and vacation rental companies. It’s not easy.

On top of all that you have to deal with maintenance, neighbors, property taxes, etc. etc.

It can be very challenging especially if your property does not age well.

With that said, in my opinion you need to hit on the hot buttons of the mental and financial costs of maintaining a vacation home or second home without sounding like a jerk.

I suggest you write a letter similar to the first letter on this vacant home prospecting letter page or model the one below.

Vacation Home Real Estate Prospecting Letter!

Dear (Name),

My name is (Name) and I am contacting you regarding your home at (name of address). I stopped by and took a quick photo of it:

Photo Of Home/Property

I understand the challenges and rewards as a vacation home owner. I am a real estate agent but I am also a recovering vacation rental property owner myself. For 12 years we rented our two homes in Truckee.

I know how stressful it can to book clients, negotiate, handle cancellations, maintain the property, arrange cleanings, pay the mortgage etc. It gets especially challenging during the busy season, right?

The reason I am contacting you is because I wanted to drop off or mail you a market analysis of your property at (name of address). There is no obligation or uncomfortable pressure.

The analysis will be tailored specifically to your property. It will show you what your property is potentially worth, and what other properties similar to yours have sold for over the last few years and there is more important information in this report that I am certain you will find helpful.

I’ve bought and sold my own retail businesses, luxury homes, and managed property successfully. So if  you are interested I can also provide my thoughts on how to boost the value of the property if that is also something you are interested in as well.

The market is in the favor of sellers right now and you never know how long that will last. Please call or email me anytime and let me know if you would like the free market analysis and I’ll have it prepared for you.

You can reach me at 555-555-5555 or

Thanks for your time,


Company Name.

Vacation Home or Second Home Real Estate Marketing Letter #2:

Dear Mr./Ms. (name),

Hello there! My name is (name) and I’m a realtor in (city/area).

I just wanted to touch base about your second or vacation home at (address). A lot of us buy these places with great intentions to get away frequently… and then real life happens. After a while, it can become clear that the second home just isn’t getting enough use to justify holding onto it.

If you’re considering making a change, I’d like to help you out by giving you a free, up-to-date market analysis with figures for other homes in the neighborhood. Having this extra information can help you as you think about your options and decide whether to keep, rent out, or even sell that second property.

Here are some tips for what to mull over as you make your decision:

• Are you getting enough use out of the property to justify paying the mortgage payments (if applicable), property taxes, and upkeep?

• How much could you expect in rent every month if you rent it out? Is this enough to cover the mortgage payments (if applicable), property taxes, and upkeep?

• Do you have experience as a landlord? Do you know someone who could be a reliable property manager if you don’t live nearby?

• How much could you expect to make if you sell the home? Will this help you with life goals such as retirement or upgrading your main residence?

Before you make a decision one way or the other, give me a call at (number) or get in touch by email at (email address) and let me know where I can send the free market analysis of your second or vacation home at (address).




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