I like to have pictures in all the blog posts I write, so you, my dear readers, don’t have to contend with an endless wall of text. In this case, there are no photos to illustrate the story I have to tell. So I’ve taken the liberty of illustrating my tale with pictures of cats. The featured photo was taken by Lou Rocco.
For you TL;DR folks or people who just want quick tips about booking vacation homes, and/or booking for a group, scroll down to the bottom.
This is the story of how booking a vacation house broke my spirit.
Usually my and Bryce’s basic rule of travel planning is to avoid tourist meccas at high season. Prices are high, pickings are slim, and every attraction is crowded up the wazoo. Who wants to pay extra money to be extra miserable? We may be crazy, but we’re not masochists.
Well, in one of those fortunate-yet-unfortunate life twists, we found ourselves having to break our golden rule. My best friend got engaged, yay! The wedding was in Florida at the height of the Christmas-to-New-Year season, boo!
Since not a single member of the bridal party lived in Florida, and we all needed to find accommodations, I had the bright idea that all the bridesmaids should find a place together and split the cost. My friend Laura suggested looking up a house on Airbnb, and I thought that was a wonderful idea.
The first step I took to destroying my sanity was volunteering to take charge of the Airbnb hunt. Yes, I could have left Laura to it. But I am a control freak and possibly crazy person, and at the time searching for a house in our budget sounded like a fun challenge—the type of thing they might make into an HGTV show. I have the worst ideas for HGTV shows, apparently.
Now, in the world of graphic design, there’s a really popular maxim that goes something like this:
How would you like your design?*
*You can only pick two.
I think accommodation-booking follows the exact same rule. Hotels or vacation homes can be cheap, nice, and/or available last-minute, but you’re damned lucky if the place you book is two of those things, and you’ve probably sold your soul if you get a place that’s all three.
It’s not my style to book things last-minute, so usually we have the luxury of finding places that are nice and still reasonably priced. I like to have accommodations booked months in advance—half a year ahead, if possible. But here was the first problem: four to five months out, no one had their flights booked. I couldn’t go ahead and book a house without knowing the dates that people were going to be in town.
So I couldn’t start looking until October, when there were two months to go before the wedding.
“That’s perfectly fine!” the optimistic voice in my head chirped. “You’re really good at finding deals! It’s not like every vacation home in the state of Florida has been booked up! There are two months to go! You can do this!”
Oh, optimistic voice in my head. You are so naive.
I dove into the Airbnb search with zeal. There weren’t a ton of places to choose from in a reasonable price range, but there were a few really good ones and that’s all that mattered. At this point, I was really picky about the places I looked for. They had to have good reviews, they had to have verified photos, and they had to have a well-written description.
I presented my findings to the group, we all voted on the place we wanted, I messaged the owners, then happily went to bed.
I woke up and found an apologetic reply in my inbox. “Sorry, someone booked the house last night,” the owner wrote.
Curses, foiled! But undaunted, I plowed ahead. I replied to the guy asking if he had any other listings available. I messaged a few more house owners. I was sure it was all going to work out.
Alas, it was all “sorry” and “no” all around.
All right. I’d just been too picky. I amped up the price filter, disregarded the presence of photos or reviews, and messaged the owner of every single result.
A tragic Greek chorus of “Sorry” piled up in my inbox. Some owners unhelpfully pointed out that they’d been booked all through December for a while, but there were openings in late January. Fear and panic started to nibble at me with each rejection. I thought my challenge was going to be finding a place that was nice enough and/or cheap enough—I didn’t know my problem would be that there was nothing available.
Here we were, with two months until the wedding, with a half-dozen people depending on me to find us shelter in Florida, and I couldn’t even deliver. In a first-world-problems kind of way, it was soul-crushing.
Guilt piled on to failure: it was too late for anyone to find a hotel deal on their own—the prices were rising by the day. By smugly promising to find everyone a good deal, I’d prevented them from having any other options. We’d all have to Couchsurf or fork over hundreds of dollars for shabby little rooms in the few hotels that still had vacancies left.
I started cursing all the families who had the gall to flock to Florida in the winter and take their kids to all the theme parks and book up all the affordable places. Thanks a lot, moms and dads and grandparents and little children who dare to have fun over winter break. Thanks a lot, Disney World and SeaWorld and Universal Studios and Legoland and Wet n’ Wild and Gatorland and Fun Spot and Magical Midway and JEEZ, Florida, do you have a freaking theme park addiction or something?
Then, out of the blue, possible salvation! One owner said his house wasn’t available, but he did have some sort of timeshare condo in a nearby resort. Would I be interested? He gave me the rates.
Then, two other owners responded. Their houses were available, and here was the total price, and did I want to book now?
The thing was, none of the options were a really good deal; in fact, with the cost split the rates were roughly twice as much as we’d all been initially willing to pay. Still, it was better than nothing. I presented the places to the group, along with the numbers.
The responses were grim. While these rates were still better than the hypothetical cost of a hotel, they were getting to the point where no one could really afford it. And while we waffled about it, our options got booked up—so they weren’t options any more, even if we’d wanted them.
My spirits sunk even lower.
Once again I went through the drill of searching, filtering, and looking at listings. This time, I wasn’t fussy about the place being nice or terribly affordable. All I wanted was “available.” I tested the waters and sent a few messages out.
Once again: “Sorry, we’re all booked through December.”
At that point, I went berserk. I was going to find us a place to stay if it was the last thing I did. I stayed up til 3 or 4 in the morning, spamming the nuts of out Home Away. It was the Night Sharon Went Crazy.
The messages I was sending at the beginning of the night were pretty chipper:
“Hello [Name]! I’d like to confirm that this condo/townhome/villa/house is still available from XX/XX to XX/XX. The listing says that the price for X nights is $XXX; is this correct? Please let me know!”
As my eyes got worn out and my hopes wore thin, the messages got noticeably more desperate. By two in the morning I was sending messages like this:
“Hello [Name], I’m trying to book a place to stay for a group of very well-mannered bridesmaids, and we haven’t been able to find anything. The wedding is in December. Is this listing still available from XX/XX to XX/XX? Please get back to me as soon as possible!”
According to my inbox, I sent out at least 52 of these messages.
Of the 52 places I inquired after, 3 were available.
Of the three, only one was really affordable. And the owner of the one available, affordable house informed me that there was another party interested in booking within the same time frame. Unless I put down a deposit, there was no guarantee that I’d get the house.
To hell with worrying if the place was nice. Of the three options—available, cheap, or nice—you can only pick two. And I couldn’t afford to give up “available” or “cheap.”
As politely as I could given the circumstances (e.g. I refrained from type-roaring “EVERYONE GIVE ME YOUR MONEY, NOW!”) I frantically messaged the other bridesmaids and asked them to send me their share of the deposit ASAP. I emailed the owner of The One House and begged, begged, begged him not to let the other people book it, that I was collecting the money for the deposit at that very moment.
Around the same time that I was hustling to collect the money and trying to convince the owner that I really was going to book the place, the bride texted me—I’d given her the address of The One House and she reported that it wasn’t in the best neighborhood.
Available, cheap, or nice: you can only pick two.
I put down the deposit, scribbled my signature on the rental form, and submitted it.
I collected the rest of the rent money from everyone and mailed the check. I got the confirmation that the house was mine for those days in December. After weeks of stressing and losing sleep, I finally breathed a sigh of relief.
And I swore to never, ever, ever do this again.
Lessons I learned about booking vacation homes
(If you’re curious about the cost of a hotel vs. a shared house, here are the general numbers I was working with. A mid-range hotel room in a decent, safe hotel at this time went for about $150 to $250 a night, per person or couple. Even if you split a hotel room among three people, that’s $50-$80 per night per person. A nice house in the same area at the same time, split between 7-8 people, would be $15-$25 per night per person, which is obviously way more affordable. I’m not disclosing hard numbers here because the process involved the budgets of other people, but if you have questions you can always ask in the comments.)
1. Start early, especially if you’re booking in a highly touristy area and/or during a high demand season. As you can see, two months out is too late to guarantee getting anything. You need to be ready to book , at my estimation, at least 4 months in advance if you want to have options, and you need to book between 6 and 12 months in advance if you are really picky.
2. Listings marked as “available” on any site are not an indication of actual availability. Although home rental sites have calendar functions with which owners can mark when their properties are unavailable, many owners don’t bother. So do not get lulled into a false sense of security when you perform a search and see hundreds of results—if you’re a few weeks or months out (see #1), chances are most of those places are already booked, even when the site says they’re available.
3. I noticed on Airbnb and Home Away that virtually all property owners have tiered pricing based on season, and they’re not automatically shown. Holiday seasons are, across the board, the most expensive time of the year. During the holiday season, a house can be twice as expensive as its off-season price. However, these higher prices are not reflected when you search (which drives me crazy). What that means is you might get a house as a search result that’s listed at, say, $100 a night, only to discover that it’s actually $240 a night for the dates you’re interested in. Always check the actual price for the dates you’re interested in, and don’t just go by the rate listed in the search results.
4. A lot of homes have a minimum stay. What that means is that you can only book the home if you stay for a minimum of X nights. I saw this more on Home Away than Airbnb, and it severely limited my options; a lot of homes had a 6 or 7 night minimum and I was booking for a period shorter than that. If you’re flexible, consider opening your booking up to a longer stay, or look at your other options.
5. There may be hidden costs in a property’s features. This wasn’t really an issue for me, since I was just looking for a place where we could eat and sleep. But if a home comes with a private pool, hot tub, grill, etc. chances are there may be additional heating and cleaning fees. If you plan on swimming, make sure you’re aware that there will be a pool heating and cleaning cost; if you don’t plan on using the pool, make sure you make that clear to the owner so you don’t get dinged by surprise maintenance fees.
Lessons I learned about booking for a group
1. Budget for a security deposit, and make sure everyone is prepared for it. I tried to do a good job of keeping things within budget for the group, and being transparent about the money; but I totally didn’t plan for a security deposit, which is pretty standard with home rentals. I felt terrible when, upon finally finding a house, I had to force everyone to plunk over additional money that they hadn’t planned on parting with.
2. Collect the money ahead of time. Properties were getting snapped up between the time it took for me to tell the other bridesmaids about them and for them to respond. It got really hairy with me sending frequent, desperate emails to hold a property open while I gathered up the money. In hindsight, it would have been a lot easier to decide on a budget, collect everyone’s share, and put down a deposit as soon as I found an available place. You can always worry about returning or making up the difference after you’ve locked the property in.
3. Know everyone’s needs and budgets. This is the one thing I think I did an okay job with. Before I started looking for places, I asked everyone what their sleeping arrangements would be, what budgets they were comfortable with, etc. I lucked out with a pretty chill group, but you may also need to inquire after other needs and ask people what their preferences and comfort levels are (if they’d rather pay more for a safer neighborhood than get a less expensive place in a shadier area, for example).
4. If people don’t have concrete dates, ask for a safe estimation. Remember how I didn’t start looking until two months in advance because people didn’t have their flights booked earlier? And by then it was already too late? I realize in hindsight that instead of waiting for people to buy their tickets and then give me the dates they’d be in town, I should have asked them all for their estimate of what day they planned to arrive and what day they planned to leave. Having to make changes to a reservation is better than waiting and then not being able to make a reservation at all.
Have any questions about the experience? Got any booking horror stories to share? Let us know in the comments!