I wrote this article article a few years ago, but it has been updated for 2019.
This February I took off for what we called a bit of a sabbatical rather than a vacation. But either way, it was great.
We rented a condo on the beach and it was SO much cheaper than the hotel-hopping vacations that we took (before we figured out how to travel for free).
So if you have a few minutes I will explain what we did and probably what we will be doing when we are going on longer trips.
How to rent a house for vacation
In December we were discussing whether or not we would be able to get away this year as we didn’t have too much saved up for a trip. I decided to hop on my favorite vacation home rental site Homeaway.com and see what was out there. Since we needed to do it in February we wanted to be in Florida since it would be fairly warm there.
After searching for about 30 minutes I had found a handful of places that had good reviews, were on the beach, were open in February, and had pictures that looked pretty promising.
They now had to pass the wife-test. As a naive guy, I am finally starting to learn how important it is for a woman to be comfortable in her dwelling (even temporary dwellings). Thankfully, we were able to land on a few that we felt good about going with.
Why rent a house or condo instead of hotels?
I had a few reasons that I wanted a vacation home (or condo) rather than using a hotel.
- Feel more “at home” with a condo. Living out of a suitcase for 3-4 weeks in a hotel was not what we wanted.
- Better food. I like to cook and having a kitchen to eat meals in not only saved us a ton of money, but it was much healthier and more enjoyable than eating out 2-3x a day.
- Hotels are so much more expensive. As you will read in a moment, we paid about (in my estimation) 75% less for our condo what we would have paid on a comparable hotel in the same location.
Now that we had found a few condos that we were interested in renting, I gave them a call. Sometimes you end up talking with property managers, but a lot of times you will be talking directly to the owners themselves. That was the case for us with the condo we ended up with.
I asked the owner a few additional questions that I had about the place and then we negotiated price a bit – which worked out awesome for us.
He normally rented his place out for $1500/month and about $600/week. But because I was flexible on my arrival and departure dates he gave us 22 days for a total of $700!
I am well aware that we got an awesome deal and things just worked out well in our favor, but honestly we would have been happy to pay $1500/month.
And the truth is that when you are dealing with a human being (rather than a hotel chain) and can help them out (by being flexible on dates) they are much more likely to do you a favor in return.
After we agreed on a price (he offered the $700 and I had no need to give a counteroffer) he emailed me the contract which I signed and sent back to him along with a deposit.
The day before we left he emailed me with all access codes and all the other pertinent information we would need for our stay.
Arriving at the condo
We read reviews, asked questions, and thoroughly examined pictures of the condo, but even with all that we didn’t know exactly what we were in for. To our pleasant surprise the place was not only bigger than than pictures made it look but also nicer!
Within a day or two, I felt like we had made the condo “ours” and we began to really feel at home with the place. For me, this was exactly what I wanted. I wanted a place to just relax – I didn’t want a non-stop typical touristy vacation, but I just wanted to chill out. This was just what the doctor ordered.
Questions about the Homeaway process
Since we had never used Homeaway, we had a few questions about the process. These were two big questions I had on my mind. Any other questions you may have can probably be answered on the Homeaway website.
What if the owner runs off with my money?
Homeaway recommends using their payment service called ReservationManager that guarantees 100% of your payment up to $10,000. This was what we did.
What if the place is not as described in the listing?
They offer a basic guarantee that provides up to $1000 in protection if it isn’t as listed. They offer a package that you can pay for that guarantees it up to $10,000 and covers double-bookings, foreclosure, wrongfully withheld security deposits, and more.
Why Homeaway over Airbnb or Craigslist?
Homeaway (aka VRBO) and Airbnb seem to be the largest places to go for a vacation home rental. I have used both many times, and I consistently find that Homeaway’s prices are a bit better.
It could just be a coincidence, but after looking in multiple cities for many trips I consistently find it to be the case.
On the other hand, I like the Airbnb user experience and app slightly more than Airbnb, but for me it doesn’t justify the cost.
And I did rent one time from Craigslist and while it worked out, I probably will never do it again. There are just too few protections that you have with Craigslist that are built in with Homeaway and Airbnb.
A few lessons learned:
- Off-season rates are a lot better. In our case, renting in the northern half of Florida seems to be off-season in February and is considerably cheaper than the southern half.
- For a lot of rentals you can use Google Maps to get a street view of the property and see the surrounding area as well – which I highly recommend doing. It will give you accurate information of what the area really looks like.
- The earlier you begin your search the better. The best places get booked up quickly, so you will find better options if you book early.