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For the average property manager, a guest booking a vacation home represents the end of the sales process. Congratulations! But for the average guest, the booking of their vacation home is just the beginning of their vacation planning. Next comes the flight, the rental car, the tickets, and all the other essential itinerary planning.

Kayak.com logo

Enter Kayak.com. Kayak represents everything that is great about the internet – it’s quick, it’s comprehensive, and it is pretty much guaranteed to give you what you want. Kayak is different than Expedia and Orbitz. Kayak is what is called a “meta” search engine. Kayak’s charge is to search all other travel search engines to help the consumer find the best option. As such, the Kayak search engine covers more ground than all the other travel sites out there. Thus you are almost always assured of finding the cheapest flight.

Kayak is a great service to help your guests book the rest of their trip. Luckily, Kayak provides some simple tools that can allow you to extend its service to your own website. By simply copying and pasting some simple html into your site you can help your guests find a cheap flight and car rental service.

For one example:

Embedding a widget like this on your web site makes it very simple for your guest to begin their flight search. It costs nothing to add to your site and can help compliment your primary service (providing great lodging accommodations).

Since most vacation home sites are regional, you can even pre-populate Kayak’s tools with the airport nearest your vacation homes. Kayak offers several simple widgets you can embed on your website. Click here to see more options.

In addition to helping your guests, you can earn money by signing up for an affiliate id via linkshare. By inserting the id into the widget on your site, you can ensure you earn a commission on anybody you send to Kayak.

Your guests look to you as an expert. By providing them with easy access to the best-in-class tools on the internet, you are setting high standards that will keep guests coming back to you every year.

Rentmineonline.com is a new U.K. based start-up striving to create an eBay-like network to enable people to rent “things” to each other. We write about Rentmineonline, because we love the idea – despite some major pitfalls.

The concept of an eBay for rentals was one of the original business ideas we explored before we created FlipKey. We looked at the world around us and thought of all the great things we’d love to have access to, but were unwilling to purchase.

  • A boat on a hot summer’s day with friends
  • A power saw to clean up some fallen trees after the latest wind storm
  • A hand bag, so my girlfriend doesn’t pay $500 for the latest craze that she will abandon in a month
  • A car to do a quick grocery run

rentmineonline.com homepage

The fact is we as a society own a lot of stuff that we don’t often use. By creating a trusted network of members you can establish a cooperative that adds new meaning to the term ‘social efficiency’.

With that said, if it was easy someone would have already done it. eBay evaluated this concept several years ago and abandoned it because of the inherent challenges. I had the opportunity to meet with Josh Koppelman of First Round Capital (and former Half.com and eBay fame) and he put it best, “to succeed you will have to inherently change human behavior.”

Josh is referring to the fact that we, as individuals, do not rent things to each other. Minus the obvious category of Vacation Home rentals, when’s the last time you rented a personal asset to a stranger?

Rentmineonline is not a crazy idea… In fact it won an investment award at SeedCamp (a European business competition) and was recently featured on TechCruch. However, Rentmineonline will have a tough road to glory. To succeed they will have to (i) build a critical network of people willing to rent things (ii) create a sense of trust out of the ether and (iii) figure out a way to monetize the process.

If they can succeed this will be a huge win for social efficiency, not to mention a very large business. As I finalize this post the market capitalization of eBay is only $49B.

We are busy at FlipKey, but we also enjoy getting out and meeting people. Over the next few weeks we will be attending a number of industry events, so if you’re in the area, please come by and say hello.

Tech Cocktail Boston 2007

What’s the hottest ticket in Boston this month? Nope – not the Red Sox. Surprisingly, it’s the Tech Cocktail Boston Party on September 6th (tomorrow night) at Tequila Rain in Boston. If you were one of the lucky few to get in, drop us a note and we’d love to meet you.
Web Innovators Group Boston logo

Next up is Dave Beisel’s Web Innovator’s Group of Boston on Monday, September 10th. The WebInno has been a great way to showcase early stage self-funded startups in the Boston area. Unlike the Tech Cocktail Party, there is no cap on attendance. Tickets are free, just make sure you register.
VRMA 2007 Showcase New Orleans Logo
Finally we will be attending and presenting at the VRMA 2007 Conference and Showcase in New Orleans this October 13-17. We will be there with booth in hand, finally ready to answer the question “So what exactly are you guys doing?”

Google Trends (trends.google.com) is a fun and useful way to keep tabs on the search volume of just about anything. Enter a term into the search box and see a graph of the term’s search volume since 2004. The real value comes when you compare two or more terms in the same graph – this provides a great view into the relative popularity of the requested terms.

The ubiquitous example in Boston is “red sox, yankees” – as you can see the two graph lines hold very close except in October 2004 when the Sox won the World Series.

Red Sox vs Yankees in Google Trends

However, this site is about vacation rentals, so we will spare you from our obsession of Red Sox nation.

What is more popular, vacation homes or vacation condos?

Google Trends: “vacation rental” vs “vacation home” vs “vacation condo”

vacationrental vs vacationhome vs vacationcond in google trends

As you can see, “vacation home” outpaces “vacation condo” by an approximately 2-1 margin. The generic “vacation rental” term makes a good baseline to compare the relative popularity of “vacation home” and “vacation condo”.

What popular vacation destination is the most searched for?

Google Trends: “outer banks” vs “cape cod” vs “lake tahoe” vs “vail” vs “myrtle beach”

outer banks vs laketahoe vs capecod vs vail vs myrtlebeach google trends comparison

A bit of an upset here – I would not have guessed “outer banks” to come in dead last. Myrtle takes the crown with the Cape coming in a close second.

While all of the above data is perfectly valid, it doesn’t give you much more than a crude directional metric. We suggest you use Google Trends as a fun exploratory tool, but avoid using it for anything beyond “oh, that’s interesting” based analysis.

For the international crowd, renting a vacation property for your “holiday” has been a popular alternative to hotel and resort accommodations for decades. Over the last several years this trend has been spreading across the Atlantic and represents a growing segment of the US travel market.

Visits to Top 5 Vacation Rental Sites

And it’s not just families trekking for a weeklong vacation at a home rental on the coast. Here at FlipKey we have experienced first hand the growth of urban vacation rentals and the increase in travelers seeking alternative lodging in places not usually associated with vacation rental travel. Our personal rental units here in Boston are fully booked and have been since the Spring.

Maybe you’re planning a trip to Vegas? Why stay on the Strip? OK, we can think of a few reasons – but the rationale of the vacation rental holds true even in the hot desert sun: affordability, unique accommodations with more space, and the opportunity to escape the madness of the hotels and retreat to your own temporary oasis and private pool. Las Vegas Retreats – Castillo Estaban.

As vacation rentals become more popular, we expect inventory to continue to grow in all vacation destinations, not simply beach, mountain and golf locations.

One of our goals at FlipKey is to grow the industry through insight and community. Over the last two months, you’ve seen our insightful contributions channeled via the FlipKey Blog. Now, as our blog traffic continues to grow, we feel it is time to start getting the community more involved.

We want to see more property managers, property owners, renters, travelers, and travel services sharing their thoughts. Whether you are an experienced blogger or you have never written a blog post in your life, we’re interested in you.

We are Looking for the Best Travel Blogs on the Internet

Have a favorite blog that you read daily? Tell us about it and help support them.

Run your own amateur blog as a side hobby? Here’s your chance to get it on the map.

Thinking of starting up your own blog? It’s easy, it’s fun, and we’re going to help a couple of you get going with some instant traffic.

Current Blogs on the FlipKey Blogroll

FlipKey has already included a handful of blogs on its blogroll. These are blogs we have come across over the last year and found useful. Some of the blogs include:

Trent Blizzard’s: Weekly industry research highlighting new marketing tactics and trends throughout the travel industry.

Mashable: Daily articles on new mash-ups – bundling open applications (e.g. Google Maps) into useful tools for consumers. We feel mash ups have a lot of potential in the travel space.

Search Engine Watch: Daily news on the evolution of Search and how to apply new strategies to improve your performance.

Slow Travel: A list of traveler blogs from around the world.

Criteria to be included as a FlipKey Preferred Blog

Our only requirements are that you fall under the “travel” umbrella, and that you post original content (i.e. no habitual blogspam). We are more concerned about the quality of the content and not how pretty it is.

How to Enter

Simple – e-mail blogcontest@flipkey.com and send us the blog link. Optionally feel free to include the blog name, the editor/owner name, the e-mail address they can be contacted at, and a short description of what you like about the blog.

What do the winners get?

  1. A spot on our Blogroll
  2. A post reviewing the challenge winners in which we explain why you were chosen
  3. Our loyal readership

And as an added bonus – just for submitting an entry, all travel related blogs will receive a permanent link on our Travel Blog Index Page (as long as your blog stays active and relevant).

How to Startup Your Own Blog

If you’ve always thought about starting up your own blog in the travel space, here is your chance. We love fresh and new viewpoints, and thus we want to help you succeed. As mentioned earlier, we’re going to reserve a couple of blogroll spots for those of you just starting out. If you’re on the fence, rest assured that starting up a blog is easy – I would recommend heading over to blogger.com or wordpress.com. Either site is a popular and simple way to create your own blog in minutes. Let them do all the heavy Web site lifting while you focus on putting up great content!

The challenge will run until the end of August. After the challenge is over we will post a follow-up with all of the inductees!

A few weeks ago TripAdvisor launched a new social networking application – the TripAdvisor Travel Map. The Travel Map is basically a Google Map that allows you to place pins at locations you have visited. You then compare your map to your friends’ maps, and bragging rights ensue. It’s a simple, but robust concept ripe with potential.

It quickly caught my eye for a few reasons. First and foremost, I’m a proponent of expanding the online travel world through social tools. The best trips I have taken have been through the itineraries recommended to me by friends and family. Second, I like Google Maps applications – a lot. Third, I’ve thought about doing something exactly like this, so I was eager to see how a solid company like TripAdvisor would approach the idea.

The TripAdvisor.com Travel Map Review

The main interface is clean and simple. I’m offered a map of the world, a column of popular destinations, and a text box to add in new locations. Upon your first visit, a simple overlay tells you how to use the map.
Tripadvisor Travel Map Main Page

I played around with various controls, adding a bunch of pins to the east coast (I own I-95!) and Europe. It was all easy enough, and there were definitely a few “wow – cool!” moments. My favorite feature is the “smart bubble” that pops up after clicking an area of the map. It picks the most likely destination areas surrounding the location you clicked on the map, and allows you to quickly pin it:

Tripadvisor Travel Map Bubble

After 15 minutes or so of adding locations, I decided to stop and see what else I could do. I clicked “save and continue”. Besides an offer to invite more friends, there weren’t any other options. Bummer.

TJ was already in my network, so I went to go check out his map. Viewing another person’s map was very similar to viewing my own map, except I could not add pins to my friend’s map. One major shortcoming that immediately struck me was the inability to overlay his map on top of my own. I consider this an essential viral feature and assume TripAdvisor will soon build a useful ‘compare our maps’ tool.

What’s missing?

While the map was a solid first attempt, there are a few crucial pieces missing. My top three suggestions:

  1. Better comparison with friends’ maps. As mentioned earlier, I need to see my map overlaid with my friend’s map. Assign a different color pin for each user on a map, and let me see it all at once. Theoretically, if I had 20 friends in my network and wanted to know who had been to Switzerland, the best way to do that would be to look at one map for everybody, not comb through 20 individual maps.
  2. Encourage users to share the map url, and offer an embedded version (widget) that users can stick on their web sites. It is not immediately clear that I can send my map url directly to others. The url that does work is not very user friendly:
    (Click here for full Link) http://www.tripadvisor.com/MemberProfile? uid=A16F630174E76997A3695112E3883723&c=pt A non tech savvy user would never guess that goes directly to their map.
  3. Give me more to do. Link directly into reviews from the map, allow me to rate the locations, show me who else has been to locations like me, etc, etc. I can think of 1001 cool things to do with these maps.

Social Travel Off to a Slow Start

Despite numerous attempts, nobody has really been able to crack the social travel network nut:

tripup.com vs imin.com vs mytravelnetwork.com

The lack of strong competition combined with TripAdvisor’s large user base could help enable them to grow into the premier social travel network on the Web. With a strong business based on reviews and lead generation, TripAdvisor can expand its share of travel mindshare by helping consumers make more personal connections through the service. TripAdvisor’s Travel Map is a simple step, but it’s a step in the right direction.

A few weeks ago, I posed a few quick questions to a group of friends.The responses were telling (feel free to play along at home):

Q: Where do you go when you want to book a flight?
A: Responses were plentiful and immediate – travelocity.com, kayak.com, orbitz.com, etc.

Q: Where do you go when you want to rent a car?
A: Responses were plentiful and immediate – budget.com, avis.com, travelocity.com, etc.

Q: Where do you go when you want to rent a vacation home?
A: A few seconds of silence. “Can you do that on expedia?”, “umm, craigslist I guess?”, “google?”

A Tale of Two Studies

Case Study #1: Finding a Flight

I need to go from Bostonto DC for a business trip on Wednesday July 18th. I want to fly out the evening of the 17th, and return first thing in the morning on the 19th.

I search on Orbitz and find this perfect flight:

Example Flight on Orbitz.com

I then search on Travelocity and find the exact same flight (for a $1 difference in price):

Example Flight on Travelocity.com

I could show you all the other travel sites, but I think you get the point. I’m going to find the same thing everywhere, so there isn’t much value in hopping around from site to site. Once I’ve picked my flight, I just click a few buttons, enter a bit of info, and my flight is confirmed. That was easy.

Travel sites aren’t fighting over inventory.They are fighting over features and usability.When that happens, the consumer wins.

Case Study #2: Finding a Vacation Home

Last year I set about to book a lakeside vacation home in Maine for a week in August.

I started at Google with a search for “Maine vacation home”, yielding results that were all over the place.

Now, I’m a picky shopper – I like to see and compare my options, read reviews on the product I’m about to purchase (rent), and generally feel like I got a good deal on something.

Take 1

I finally picked the “perfect” house and e-mailed the owner. The owner responded a few hours later saying “I’m sorry we are booked for that week. “Booked?” But the calendar showed the property as open, both before I sent the e-mail and after I received the owner’s response.

Take 2

I found another nice property, and sent my second inquiry. Two days go by and no response. Who knows if my inquiry even made it to the recipient via the form I filled out. I resubmitted. Still nothing. I guess that’s a no.

Take 3

I find a third place that I didn’t like nearly as much as the first two, but I was tiring of the process. It’s available, the owner responds, great. I fill out the agreement and send them a check. Fast forward to my stay there – I’ll share the details another time, but suffice to say, I would not stay there again.

To recap, all I wanted to do was book a vacation home for some much needed R&R.Instead, I spent the better part of a week dealing with three different people amidst calendar and responsiveness issues, only to end up at a falsely advertised property.

Vacation Homes Need a GDS

Compare the two experiences. The airline industry is a well-oiled machine. The vacation home industry isn’t.

Most sectors of the travel booking industry have been commoditized. The reason for this is the airline industry, as well as most of the travel industry, is all interwoven via Global Distribution Systems (GDS). GDS’s (such as Sabre, Amadeus, et al) maintain large data stores of information about airline flight information, schedules, prices, reservations, etc. So when you search for a flight on Orbitz or Travelocity, what is happening is the site is tapping into one of the Big GDS systems, and you basically end up with the same search results at every site. I know in real-time what my best options are, how much they will cost, and whether the option is truly available or not.

The existing GDS system will not work for vacation homes due to the fragmentation of the marketplace, but the industry needs to begin pursuing a workable global integration system/solution. Currently, listing sites and industry software solutions all work in a bubble creating firewalls of inefficiency. The internet has liberated several verticals from self imposed growth limitation and it’s time we begin discussing the next generation of the vacation rental experience.

We have said this before and we will keep saying it “the vacation market is not a zero sum game”. There are tremendous opportunities for growth but we need to begin opening up solutions and working together to realize the marketplace’s potential.


We started FlipKey to help expand the vacation rental market by providing a platform to highlight professional reputation and trust. There are 6.5 million vacation homes in the U.S. and less than 10% are rented to travelers looking for a great place to stay. This means over 5 million secondary home-owners are foregoing the economic benefits of renting their homes when they are not occupying them. We are convinced there are simple solutions to help bridge this gap.

The FlipKey Blog is our first contribution to the rental community. The founders of FlipKey are passionate about the internet and how it can improve the home rental marketplace. We have industry-leading research, insightful observations and opinions we want to share.

The humble goals of the FlipKey Blog:

  • Encourage more owners to rent their homes and more guests to rent vacation homes.
  • Provide free access to premium research that has never been available to the vacation rental industry.
  • Cultivate a sense of community and thought leadership among property managers, listing services and owners to expand the vacation rental marketplace.

FlipKey’s core service is still in development and will be launching this Fall. If you are a property manager, homeowner or are involved with the vacation rental industry and would like to be included in our service launch, please contact us at chartermember@flipkey.com.

Enjoy the Blog and we look forward to your thoughts and comments.