I used to work for a vacation rental management company.  I have seen the good, the bad and the ugly.  Screen your guests thoroughly! Provide a thorough guide for guests to avoid constant calls (cover everything from nearby restraunts to where the breaker box is located). A good rule of thumb when looking at properties is that no more than 4 guests should be sharing one bath.  Avoid full size beds, adults tend to prefer queen size beds or larger.  When decorating think of it like staging, less is more.  White sheets are great, they can be cleaned easily.  Install a schlage lock or something similiar it will allow you to set a new access code for each guest.  Feel free to reach out for more info, I could go on and on for days!

For many years, we owned an oceanfront property about a 5 hour drive from our home.  

While the management company was competant (and we found out over the years, they are mostly the same), we did find that had we not had someone local to check on things on occasion, our expenses would have been much higher because we would have been relying on the property management company to do even the smallest of things.  (Oh, need a light bulbs?  $25 for a service call, please). 

For the most part, we had great tenants, probably because they were mostly repeat renters.  But there are always those people who think because they are paying $$$, they don't have to respect your property. Think suntan lotion on your furniture, as an example, or those tenants who help themselves to batteries out of the tv remotes and smoke detectors and all the light bulbs.  Yes, you cannot make this stuff up.  

The cleaning crew is there to clean quickly and turn over the house;  we had someone local do a "walk through" on turnover days to insure there was nothing the next week's tenants could complain about...missing lightbulbs,  missing tv remotes. dirty filters, stains on bed coverings, that sort of thing.  It's those seemingly small items that can run your expenses up pretty quickly because when the property management company has to replace batteries and lightbulbs, they charge you a marked up price for the items as well as a minimum service fee.  

As for general maintenance, again, we had a local list of folks who could get to the house quickly and at a fraction of the cost of the property management company;  we had the company call us directly if there was anything wrong (A/C, etc) and we dispatched someone.  Again, it kept our expenses way down and allowed us to be cash flow neutral. 

And because we were only 5 hours away, we could get down there in the event of something major, especially after hurricanes and nor'easters, again, saving a lot of money on hiring everything out.

The pros?  It can be a good investment (we were lucky, bought in a low market, sold in a high market, doubled our money and were cash flow neutral during the period we owned the house).  

The cons?  You sometimes are made aware of human behavior you wouldn't expect and even in our minimal dealings with tenants (it was unavoidable sometimes when they could not figure out how to work the tv or the gas grill that you had to talk to them directly), it was on occasion frustrating.  

I believe tax laws are such that you cannot use it on a regular basis unless you "close it for maintenance."  So, in the off season, we were there often working on it (oceanfront properties take a beating and require a lot of maintenance) and knew to keep all receipts.  ;-)

From our experience and what we learned from others, we would only have a relatively small place vs one of the larger "mini mansions" simply because those places really take a beating since multiple families would pack in them week after week.   While we heard plenty of horror stories, we were very blessed to have had an overall great experience. 

Would I even think of doing it without a property management company? Oh, heck no, it's not worth the time and aggravation.  Just negotiate a good rate (yes, they are negotiable but don't tell them I said so LOL) and let them handle the majority of the issues.  

I do not

Not currently; however, some great answers here.

I don't... I don't vacation in the truest sense of the word. I don't rent for myself or for income. 

We do in Florida and we have the best results with VRBO. Airbnb has an inferior site and we finally just cancelled out on it. 

I do not because I made my vacation rental my full time residence a couple years ago. I always ask my clients, "What are you trying to accomplish with a vacation rental?" If it's appreciation, beware that resort areas tend to have wider and quicker swings in value when the economy falters. If you vacation in the same area frequently, then a vacation rental can provide you several benefits: 1) You know that you love where you are vacationing and there are no surprises in the accomodations. (2) You can utilize your owner's closet which means you can travel lighter, and you will already have most of your neccessities which means you don't have to rush to a store as soon as you arrive. (3) You let others provide you practically free vacations. You can make enough rent to pay insurance, property taxes, hoa fees, utilities, and some! 

Nathan Gesner - not yet!

Though I may not own in future either.

Too old to enjoy for a long period of time, I guess.

Nathan,

Looks like Erika Albert has a great answer. A

My partner Melissa owns two: Maui & Costa Rica, want to chat with her?

I have 2 clients that turned condos I sold them into short-term rentals and VRBOs, no Air B&B though.

I have two, one in Colorado and one in AZ. Colorado with Air BnB. Az with Homeaway , which owns Air BnB. We just purchase the AZ Home. But will be putting it in both, We are targeting Canada Folks. The Colorado cabin is killing it, 650 sq foot cabin average  1800 a month. three months over 2200 We started in Sept. Love it, easy. Combo door lock and a cleaner and send the the house info and they just put the money in my account... Great write off and Fun to manage. It will be supporting my retirement.. Whoo hoo. 

Ack! I swear I wrote a whole decent sized answer on here this morning and apparently it didn't post....-Kasey

No.  I have a friend with a couple of them and he says it's almost a full time job keeping them rented.

My vacation rental is the Ritz Carlton ... needless to say, I do not own it. 

I do not....but I rent on the beach at Cape Cod MA..... we're going the week of the 4th....

This is a decent question...Lets find out Nathan

No.

I don't.  The only advice I have is to be prepared to deal with the worst in the public.  Or, get a professional property manager.

We used to own a few but we moved to where they were LOL

My advice depends on why you want the rental - for income + vacation/vacation only/retirement + vacation?

Have a good management company you can rely on if you are not local.

I sold mine, because i could not go on vcation being too busy taking care of Saturday move in and move outs every week of summer. Giving it to someone else to manage proved they rent to anyone and did not care about the property itself like i did

We do not.

Not any longer. Erika Albert provided some great answers.

I do not, but I do own a cabin

I don't personally own it but, family does. Pros - we can use it when we want to be at the beach!  Cons - Renters don't care as much about the place as we do!

      Use a site like VRBO.  

We have owned a condo with our best friends for 23 years. We have never regretted it and never had a fight about it. We made rules at the beginning and stick by them. None of us feels lke the other couple takes advantage of the other one. We have let our families and extended families use it. That is one of the rules too.

I did for a number of years.. I do have pros cons I would be happy to share my personal experiences with you.. feel free to EMAIL me directly arrange a time to talk.

Merry Christmas 

I do not, as I like to go different places on each vacation.

No; never have and never will. Too many diverse spots I intend on visiting in my elusive spare time.

I have a licensed B&B on my property. cottage and it works pretty well. 

I do not have, but a lot of friends use airbnb for backup solid income these days. 

My rental properties have always been residential but I've never owned a vacation rental.

My most effective rentals are those within a half mile of the office.

But rentals of hunting land and cabins do help to pay the taxes.

No.

Sorry Nathan, do not have one, Yellowstone does not have any for sale.