Our Experience With Vacation Rentals

Share with a friend

Update: Since this post, I’ve stayed at multiple Airbnbs and have had excellent experiences. In the early days of Airbnb there were a lot of issues. Both Airbnb and the hosts have evolved and I use Airbnb frequently.

Wanting to avoid the crowds and hang with the cool kids on Oahu’s East side when the cheapest room at the Turtle Bay Resort priced at $2800, the equivalent of Venezuela’s 1993 GNP, needing two rooms, I decided to check out vacation rentals through Airbnb, VRBO, and Homeaway.

I tend to book directly with a property and with the exception of using a travel agent, I’ve never used a third party intermediary, using Airbnb, VRBO, and Homeaway was a new experience.  One that wasn’t without a few bad apples.

This will be part one of a three part series featuring our experience with vacation rentals, specifically our experience with Airbnb, VRBO, and Homeaway.

Part 1: Garage Sale Mentality on Airbnb

Part 2: VRBO: Sixteen Going On Seventy

Part 3: Just Like Home With Homeway?

Garage Sale Mentality on Airbnb

Although I had heard of Airbnb in passing when Ashton Kutcher became an investor, I hadn’t met anyone who had used the service until recently.

Last month at TBEX I met several travel bloggers who backpack, stay in hostels, couchsurf, and experience alternative lodging that aren’t always an option for families.  Finding lodging when you travel can be challenging, add in a couple of kids and it adds a new dimension.  “Hey buddy, can we crash on your couch? By the way, there’s four of us.”  Probably isn’t a common request on Couchsurfing.

Since Aaron from Aaron’s Worldwide Adventures mentioned he had great experiences with Airbnb, I gave them a try.

Having found several homes that met our basic requirements: beds (as in plural, I’m not paying to sleep on a floor) and $2000 or less for the week (food is good), I contacted one of the listers, we’ll call him Travis (because that’s his name) and waited for a response.  And waited.

No response after four days, with time running out we contacted a second Airbnb lister (wondering if we would be singing Fool Me Once along with B.B. King) while also contacting someone from Homeaway.  (More on our Homeaway experience in part 3 of this series.)

Our experience with Travis could have soured us on Airbnb, were it not for the second Airbnb lister, Daria.  Daria responded within a day, but alas it was a few hours after we had already committed to the Homeaway listing.  While our Airbnb experience wasn’t an entire wash, we did learn a few things about Airbnb.

What we learned and what everyone should realize about Airbnb:

a)  Joe the Plumber

Airbnb listers are regular people.  The majority of listers on Airbnb are people like you and me vs. hotel chains.

b) Garage Sale Mentality

Airbnb is primarily composed of people who are not running a business. People who are looking to make extra cash.  Airbnb is not their primary source of income. Like a garage sale, you have one when you want to make a little extra money, don’t have one when you don’t need to.  On Airbnb, you list your property when you’re short of cash, remove it when you’re flush.

c) Life can get in the way of responding to emails

Emails can get lost in the shuffle. We’ve all been there.

d) Hedge Your Bets

It’s ok to contact several Airbnb listers at the same time, they expect it and you won’t lose time waiting for someone to get back to you.

e) Exceptions To The Rule

With everyone, there can be exceptions to the rule. Our experience was Daria was an exception.  I hope more of the Airbnb listers are like Daria.

In case you’re wondering if we ever heard back from Travis…he responded two weeks after we contacted him.  Turns out the place is on the market and has since been removed from Airbnb.

What type of experiences have you had Airbnb?

Save $40 when you stay at Airbnb.

Traveling Well For Less has partnered with Your Best Credit Cards for our coverage of credit card products. Traveling Well For Less and YBCC may receive a commission from card issuers.

---

Chase Sapphire Preferred® Card

The Chase Sapphire Preferred® Card is the best card to get started in the world of miles and points. It is the first card you should get to start traveling for free because the welcome offer is 60,000 points after spending $4,000 in the first three months.

 

My favorite perks about this card are earning 5X points on travel when booked through the Chase portal (2X if direct purchase), 3X points on dining, $50 yearly credit on hotels booked through the Chase portal, no foreign transaction fees, and transferring points to 13 airline and hotel partners like Hyatt, United, and Southwest.

 

Learn more about the Chase Sapphire Preferred® Card and how to apply

---

Chase Freedom Unlimited®

The Chase Freedom Unlimited® is one of my favorite cards for earning cash back card and travel rewards. It offers a welcome offer of an additional 1.5% cash back on all your purchases up to $20,000 your first year.

 

My favorite perks about this card are earning 5% cash back on travel booked through the Chase Travel Portal, 3% cash back at drugstores and restaurants (including delivery and takeout), 1.5% cash back on all other purchases and no annual fee. When paired with cards like the Chase Sapphire Reserve® Card or Ink Business Cash® Credit Card, you can use your points to travel for free.

 

Learn more about the Chase Freedom Unlimited® and how to apply