How to Book the Perfect Vacation Rental in Palm Springs (Or Anywhere Else, for that Matter)

Insights from an Owner

Image for post
Image for post
The Elrod Villa: Our little slice of mid-century modern paradise.

[ Update 7/13/17: While much of this article still applies, some of it is somewhat out-of-date. You might be interested in my new article, “Vacation Rentals in Palm Springs: Tips for the Savvy Traveler” which covers some of the same material in a more up-to-date way.]

After many years of visiting Palm Springs (usually staying in vacation rental houses), my wife and I finally found the ideal vacation home of our own last year — a place with architecturally-significant, mid-century modern design, a private pool and spa (and fountain!), great furnishings, and a track record as a successful vacation rental. We continue to run it as a vacation rental when we’re not enjoying it ourselves and it’s been fun and interesting (and, at times, frustrating) to learn about the vacation rental market from the owner’s perspective over the past year.

This post encapsulates and greatly expands upon some of the tips — about how and where to inquire about vacation rental properties — that I frequently share with guests who inquire with us at Elrod Villa (particularly those who, for some reason or another, we’re not able to accommodate). Along the way, I share some general tips about the Palm Springs vacation rental market in particular. But I suspect that much of this information will be of use to travelers seeking a vacation rental in any locale.

tl;dr department: I own and operate an insanely cool vacation rental property in Palm Springs, California. I’m gonna drop knowledge on you about how to inquire with vacation rental owners in a way that maximizes your chances of booking the place you want — and maybe score a discount. You’re gonna learn why the site(s) you use are a big factor. Some of the info is specific to Palm Springs, but I bet it’s helpful anywhere.

Palm Springs has been undergoing something of a Renaissance as a vacation and event destination over the past few years. In a city that was once very seasonal in terms of tourism, there are now significant events almost year-round. (July, with its sometimes hellish/dangerously hot weather is the notable exception.) This trend has been a boon for local hotels (which quickly fill up well in advance of popular events and holidays) and spurred a number of new hotel projects, not all of which have yet come to market. As a result, vacation rentals have become an even more attractive lodging alternative for visitors.

Image for post
Image for post
Elrod Villa interior: Yeah, it’s a little fancier than your average Radisson.

But finding and booking a vacation rental isn’t quite the same the same as booking a hotel. The various home sharing, travel and vacation rental websites have tried to aggregate inventory, simplify searching and reduce the “friction” involved in transacting business between travelers and vacation rental operators, with varying degrees of success.

For the first-time vacation renter, the process might seem daunting — and, despite all the hoopla about sites like Airbnb, a brand new survey from Pew Research Center shows that just 11% of Americans have used a “home sharing” site like Airbnb or VRBO.

How to Inquire about a Vacation Rental

While Maximizing your Appeal… And Without Wasting Your Time

In the later part of this post, I go into quite a lot of detail about what differentiates the different vacation rental sites. But, regardless of the site that you inquire and/or book from, these are some tips you should know. Unlike booking a hotel, where all they need to know is your dates-of-stay and a valid credit card number, many vacation rental owners or managers are looking for a little more info.

You’re looking to rent someone’s home. At the very least, you’re looking to rent someone’s pretty-darn-expensive investment. You can bet they are at least a tiny bit interested in who you are and concerned about your suitability as a short-term occupant of their property. Here are the additional things that owners want (and in some cases need) to know, even in your first contact message or with your “Book it Now” request:

  • Your age (or at least your age range): It’s not about age-ism. Some properties are better suited to certain age ranges than others. In our case, our sweet-spot is probably people in their 30s-50s+. I think it’s great for guests in their 20s as well, but here’s the thing: The City of Palm Springs won’t let me rent to you if you’re under the age of 25. Yep, I think it’s stupid, too. But we are licensed by the city (all legal vacation rentals here are licensed as hotels) and that’s one of the rules. So, at some point, I’m required to know your age, as well as the ages of your guests, so might as well tell me up front.
  • What’s bringing you to Palm Springs: I’m not trying to pry, but it’s useful to know. “We’re celebrating our Xth anniversary away from the kids!” Well, I’m a sucker for anniversaries. I’m likely to offer you a bit of a deal. And don’t be afraid to mention that you’re coming to town for a special event, like a major conference or concert event — you know, the kind that causes rates to go up and for their to be competition for the best properties. In those types of situations, you can be sure that I’ve gotten multiple inquiries over those dates. And my rates are likely already adjusted well in advance. What I’m looking for is the most suitable renter(s) over those busy periods. “We want to chill by your awesome pool after a day of raging at Coachella,” doesn’t bother me.
  • Why you’re inquiring about this particular property / show some personality: I understand that you may be inquiring with a lot of different properties. But one key way I can differentiate a truly interested renter from one who’s just “kicking the tires” is whether they make some specific comment about our place. Doesn’t have to be complicated: “The bar looks awesome.” “Love the design of your living room.” Etc. Or maybe tell me something about yourself: Are you a fan of modern architecture, a musician, a marketer, into cocktail culture, into cool art…? Me too!!! You never know how you might connect with somebody.
  • Whether your group includes children or pets, or if you have other special requirements: The different vacation rental sites all screen for “suitability” in different ways… some better than others. It really helps to actually read the description of the property and check suitability before engaging with an owner. Specifically: Some properties are pet-friendly. Some don’t accept children. If you have either of those, take a moment to review the details of listings you’re inquiring with before sending an inquiry or booking request. In our case, we don’t allow pets (not suitable) and we don’t allow children under a certain age (not safe or comfortable for them). So while some of the vacation rental sites allow you to note number of children or presence of pets, many will still send us your inquiry… And I unfortunately have to decline your booking. On the positive side: at Elrod Villa we strive to provide a truly amazing vacation rental experience. True story: We had a guest who said, “My partner is a sun worshipper, but I’m allergic to the sun. Do you happen to have a pool umbrella?” I had to confess that I didn’t, but I wanted their business, so I bought a really great pool umbrella… just for those guests. Also, if you read our fine print, you’ll find that we do allow smoking (well, outside)… But that’s rare in California!

tl;dr department: Whether you’re making an inquiry or submitting a “Book Now” request, including a short note that includes your (1) age, (2) the reason for your visit, and (3) why you’re interested in this particular property or something about your personal interests and experience greatly increases the chances of an owner accepting your booking or replying positively to your inquiry request! Don’t be shy and don’t lie. Additionally, if you have pets or children in your group, take a moment to review the “suitability” section of the properties you’re interested in.

Where to Look for Vacation Rentals in Palm Springs (and Similar Resort Destinations)

What are the differences… And what difference does it make?

Having a little knowledge about the differences between the various sites can also help you find and successfully book the ideal vacation rental for your trip. Here’s a quick (well, quick-ish) rundown of the top options and how they might impact your overall search and booking experience. / /

Whether you’ve ever heard of these sites or not, in resort destination markets, these are the ones that are most likely to connect you with your ideal vacation rental.

In Palm Springs, the HomeAway family of sites —, and, all of which share a common interface— has the largest inventory of vacation rental properties, somewhere in the neighborhood of 2000. And with good reason: Unlike more recent entrants like Airbnb, HomeAway and VRBO (“Vacation Rental By Owner”) started out to aggregate listings for the pre-existing vacation rental market and have interfaces and policies that are well-suited to professional rental management services as well as vacation rental owner/operators. They’ve been doing this for a relatively long time (VRBO started in 1996, HomeAway in 2005) and have accumulated the greatest number of listings through both organic growth and via acquisition/merger.

So, if you’re searching for a vacation rental in Palm Springs, start there. And you don’t need to search all three — they’ll all return the same results and you’re going to get the largest number of results over the other services. My experience as an owner has also been that these sites provide the best experience in terms of communication, ease of transacting business and serving the unique needs of vacation rental owners and guests. I’m always happy to take bookings through HomeAway/VRBO. In fact, more than 90% of our successful bookings in the past 11 months has come through those sites.

From an owner’s perspective, some of the things I like about HomeAway are:

  • Communication: Guests and hosts have more flexibility in terms of how they communicate. When you inquire with us there, we can communicate with you via email and phone, should we need to. We can see each other’s actual identities, names, and contact information. (On other sites, guests and hosts are more “walled off” from one another. It’s often claimed that this is about safety or privacy, but the fact is it’s out of concern that hosts will take business out of the marketplace. More on this later.)
  • Payment and policies: HomeAway has a payment processing system that works fine (takes all credit cards, decent processing fees — which are deducted from what the owner gets). Importantly for vacation rentals: if you’re making a reservation far in advance, and the owner has a policy such as “guest pays half now (to reserve) and the balance 30 days before check-in” (which is very common and, in fact, how we do things at Elrod Villa) the owner actually receives those funds for the rent payment. In other systems, the marketplace holds on to those funds, only releasing them to the owner at check-in. (So, thinking about it from the owner perspective, you can probably see why that’s attractive, especially for a reservation that’s far out into the future.)
  • Damage deposits: HomeAway actually handles damage deposits sensibly. Which is to say, if the owner requires a damage deposit, the damage deposit is charged to the guest and then held, essentially in escrow, by HomeAway. When the guest checks out, the owner has a couple of days claim any damages (which would be deducted from the deposit), otherwise the deposit is returned in full. (Pro tip for renters: If you’ve not done any damage, ping your host and let them know. They can have your damage deposit refunded earlier.) Alternatively (or along with a deposit), the owner can require a “Property Damage Protection” insurance policy provided through a HomeAway partner (and even if they don’t require it, you have the option of adding it — along with a similar “Cancellation Protection Policy” that can protect you in the event of an unforeseen cancellation).
  • Rental agreements: HomeAway and its related sites understand that what they are doing is brokering a transaction between a traveler and a home owner/manager. They understand that, in nearly all cases, the owner or manager is going to have some sort of agreement directly with guests. And a sample of the rental agreement can be uploaded to the site so that it’s automatically included with any quotes sent to inquiring guests (this is what we do at Elrod Villa).

From a guest perspective, I think that most of the above is beneficial, too, but the main benefit to guests is that these are the sites that have the largest and best variety of inventory (the vacation rental listings) in resort markets. Also, because their policies and procedures that are mostly in sync with owner/manager needs, owners are more likely to accept a reservation. You don’t want to be wasting your time, right?

Here are a few more HomeAway/VRBO-specific tips for prospective guests:

  • Inventory: That these sites have a great deal of inventory can also make searches more difficult (you’re going to get a lot more search results!). If you’re interested in the most streamlined experience, use the “Booking Type” pulldown to set both the “Book It Now” and “Offers HomeAway Payments” options to checked. This will present you with only those properties that are immediately quotable/bookable online and where your payment can be taken directly through the site. Additionally, don’t be afraid of the “More Filters” button — this is where you’ll find options to filter for number of bathrooms, amenities such as a pool, etc. (Aside: I find that, in Palm Springs, if you click “Pool” your total number of search results is cut roughly in half. If you’re looking for a place like Elrod Villa, you’re looking for a private pool. Might as well eliminate the places that don’t have that, right?)
  • “Service Fee”: Before you think this post is a love letter to HomeAway/VRBO, there are some things that I don’t particularly love. The (recently introduced) service fee for guests is one that I’m not thrilled with. These sites charge a listing fee to owners — we pay to have our properties listed and/or featured there —and it used to be that guests didn’t pay anything at all to use the service. These sites now add a Service Fee for guests that’s added to the quote as a separate line item (computed at 4–9% of the total rental cost excluding fees and taxes). This change has been a cause for a great deal of angst in the HomeAway owner community and its impact is still unclear. Different owners are dealing with it in different ways. In some cases, you may be able to get an owner to reduce their rental rate or other fees to offset some of the Service Fee (but don’t count on it). This is such a complex topic that it probably deserves its own post in the future.

Pro tip: A sure way to get around booking/service fees is this: If you find a property that you love on any of the listing services, Google its name and see if you can find direct contact/booking information and reach out to the owner/manager that way. You have the best chance of getting the best deal that way and the owner will thank you for it.

  • Hospitality Content: One unique HomeAway feature is that owners can create a digital version of their compendium (you know, that binder full of information about their policies, info about the house [where’s the trash go, again?], local recommendations, etc.) that is then available to guests through the HomeAway/VRBO smartphone app. We use it and I think it’s a terrific idea. The whole of human knowledge is available through your phone — it should also be able to tell you how to turn on my stereo, amiright? It’s just one of those neat features that makes HomeAway a little more “sticky” for owners (possibly for guests, too).
  • Cancellation and Property Damage Insurance: As mentioned previously, whether the owner requires it or not, guests can add property damage insurance to protect themselves against damage claims. Similarly, HomeAway makes it easy to add Cancellation Protection insurance, which is a smart addition for certain types of rental situations (see this summary for details).

tl;dr department: and its related sites have the largest inventory of vacation rentals in Palm Springs and similar resort markets. Their owner-friendly policies and guest features increase the likelihood of a successful booking and overall vacation rental experience (but not necessarily at the lowest cost — which is almost always to be had by booking directly with an owner/manager should you be comfortable doing so).


If you’re new to vacation rentals, this is probably the site you’ve heard of (and it might be the only one you’ve heard of). As of July 2016, data from (an Airbnb market reporting service) shows that there are approximately 1600 “entire place”/whole home vacation rentals in the Palm Springs market listed on Airbnb — so, less than (but close to) the inventory of VRBO/HomeAway. But Airbnb has huge “mindshare” and listings are free for owners, so you’ll find Elrod Villa there along with many other vacation rental properties.

I think the concept of Airbnb is pretty brilliant. The founders essentially set out to “disrupt” the concept of lodging, having recognized that there was a huge untapped resource in extra rooms in people’s homes or in gaining access to entire homes when, for example, the owners are on vacation/out-of-town/what-have-you… Essentially turning homeowners into “sometimes but not really” vacation rental operators and hoping to lever that into being a powerful force in the travel industry at large. (I’m really being reductionist here, but this isn’t a treatise on the genesis, history and impact of Airbnb.)

Professional vacation rental operations are quite different and, in resort markets like Palm Springs, Airbnb isn’t particularly appealing for owners, but its become a necessity to list there. Let me just reiterate the “pro tip” from above: If you find a place that you love on Airbnb, and you’re comfortable dealing with the owner directly, Google the property’s name to see if you can find direct contact information and try reaching out that way — the owner/manager will thank you for it…

There are a couple factors that make inquiries/booking requests from Airbnb less attractive from an owner’s perspective:

  • Communication: This is the big one. In Airbnb, guests and owners are more walled off from each other. Prior to accepting a booking, we can communicate via text-based messages, but we can’t communicate via phone. I have less of a sense of who you are. And, if you really need me to sell you on my property and want to speak with me (or if I have a concern about you and want to chat), we just can’t do that. I can’t even share outside links with you. For example, if you’re crazy for midcentury modern architecture, I might want to share the Architectural Digest article about our home with you. Can’t do it. Or if I want to share our Instagram or Facebook page with you… also, can’t do it. This keeps owners from taking business “direct” with guests or funneling them to some other service (which is totally understandable) but it often gets in the way of negotiating a successful booking. In fact, if we are unable to accept your booking and I want to point you to this article to give you these helpful pointers, I can’t even do that. Just know this up front.
  • Policies: Unlike HomeAway, Airbnb doesn’t release your payment to the owner until 24 hours after you check in. For a reservation that’s in the near future, this isn’t generally an issue. But if you’re inquiring about booking far in the advance or booking a longer-term stay, your inquiry is substantially less attractive than one that comes through HomeAway. Also, if your booking is far in the future, you won’t see every available property — some owners only allow booking via Airbnb within a short time frame (e.g., 90 days into the future) and you won’t see them listed for dates outside of that booking window.
  • Rental agreements: Support for custom rental agreements is pretty poor and not fully supported by Airbnb’s interface (though it’s not against their policies). We just end up having to exchange and execute such agreements this after accepting your booking on Airbnb.
  • Damage deposits: Support for damage deposits and damages to property is non-existent in a traditional sense. While I can specify a damage deposit (called a “security deposit” in Airbnb speak) those funds are not charged to a guest in advance. If a guest damages a hosts property, the host needs to file a claim against the damage deposit within 48 hours of checkout and the issue is handled as something akin to a dispute resolution. This is probably acceptable for “home sharing” type arrangements, but doesn’t always meet the needs of professional vacation rental manager/owners.

On the plus side (no particular orientation toward guests or owners on this one):

  • Booking experience: Overall, potential guests seem to like the Airbnb booking experience, which has the surface appearance of being “hassle free” and trustworthy. Know that there are some drawbacks. For “entire house” (non-home-sharing arrangements) don’t be surprised that you’ll likely have to complete a rental agreement (which, hopefully, the owner/manager does entirely electronically, as we do at Elrod Villa) and that pre-booking communication can feel limited.

Note also that Airbnb bookings must be paid for, in their entirety, in advance. When booking direct with an owner, or through channels like VRBO/HomeAway, many require only a portion (typically half) of the rental price up front with the balance due about 30 days before actual check-in. (This is fairly traditional in the vacation rental world.) On the flip side, Airbnb does not collect a damage deposit in advance in the traditional sense.

  • Home share: If you’re looking for a true “home sharing” experience (where you are renting an extra room with a host who is also in the home), this is the only game in town. If you’re looking to rent a whole house just for your group, there are better options.
  • Design/interface/tech: I think the overall design and interface is pretty good (and there’s some very powerful technology under the hood, including things like built-in dynamic pricing for hosts) and they have the resources to make it great eventually.
  • Potential to be a great vacation rental resource: If Airbnb should choose to make their site and policies more vacation rental owner/operator friendly. I suspect they have bigger fish to fry, however.

tl;dr department: You’ve surely heard of Airbnb, but (from an owner’s perspective) know that it’s not necessarily the optimal solution for booking vacation rental properties in resort destinations like Palm Springs. Airbnb can work for you if you’re sure about the property you want to book, the booking is not extremely far in the future, and you are ready to pay. And if you’re looking for a “home sharing” scenario, it’s the only game in town. Could evolve to be the “go to” source for vacation rentals should they choose to do that.

TripAdvisor Vacation Rentals /

The vacation rental services operated by online travel giant TripAdvisor, TripAdvisor Vacation Rentals and, have a decent amount of inventory of vacation rentals in Palm Springs, but significantly less than that of HomeAway — something on the order of 50–60%. The two sites have slightly different search and search results presentation interfaces, but I believe they expose the same inventory. The vast majority of the listings that I see there are also found on HomeAway (and honestly, I’m not sure if any are, in fact, unique to TripAdvisor). My sense is that these sites are performing poorly for most owners in resort destinations and anecdotally inquiries from them have plummeted in recent months.

I really want to like these sites, but from an owner’s perspective, inquiries that come through them are less attractive than inquiries via HomeAway/VRBO for reasons that will become apparent. But let’s start with what I like about them as an owner:

  • Free to list: Listings are free for owners. The TripAdvisor/Flipkey business model is to take a percentage of the price for each booking. Some of this comes out of the payout to the owner (i.e., a commission), and some is paid by the renter (i.e., a booking fee). So, even if no bookings ever come through them, the listing is a free marketing vehicle (all it costs me is a little time to set up). And, at least theoretically, the reach of these sites should be huge as travelers use TripAdvisor to plan their trips and research destinations.
  • Design: I find the search, search results and listing views to be slightly superior to HomeAway’s. For one, TripAdvisor allows more pictures (HomeAway is limited to 24, which I find weird). The design of the search and search results interfaces is also a little more “modern” than HomeAway’s.
  • Rental Agreement and Damage Deposits: These are handled similarly to HomeAway. Sample rental agreement is shown as an attachment in quotes sent to guests.
  • Payment: TripAdvisor sites accept all the expected payment methods from guests so that’s neutral vis-a-vis HomeAway. Like HomeAway, these sites have a Book It Now option that allows guests to signal that they really want to book this particular property and are prepared to pay right now.

There are a couple factors that make inquiries/booking requests from these sites less attractive from an owner’s perspective:

  • Communication & Policies: TripAdvisor/Flipkey have the same limitations as described in the section on Airbnb, above, so I won’t belabor them here.

tl;dr department: The takeaway for renters is this — TripAdvisor / Flipkey could work for you if you’re sure about the property you want to book, the booking is not extremely far in the future, and you are ready to pay. To maximize the chances of your request being accepted, use the “Book It” option, don’t just send an inquiry. If you’re researching properties and want good pre-booking communication with owners, use HomeAway (described above) or (described below).

This is a weird one and I almost didn’t mention it except that we actually get a good number of inquiries through this site. is owned by TripAdvisor, but it has a completely different orientation than FlipKey. It’s almost purely a marketing site (owners pay to list there) and it doesn’t presently have an integrated quote system or payment system or any of those fancy things. It simply offers nice-looking listings, a calendar, a list of rates, etc. and puts would-be renters in touch with owners. It has a small-ish (about 300) but growing inventory of vacation rental properties in Palm Springs.

But we list Elrod Villa there (here’s the listing for Elrod Villa) and get a decent number of inquiries. Inquiring with an owner on that site might be your most cost-effective route to booking a vacation rental property in Palm Springs because:

  • No booking fees: When you get in touch with an owner here, you are contracting directly with them. No middle-man, no extra fees.
  • No bogus restrictions on communication: Once we make contact, we are free to engage however we like. In fact, I could even funnel you to another site to complete your transaction, if that’s in both of our interests.

But on the flip-side it has:

  • Limited inventory: Small-ish number of properties listed, but potentially gaining traction in Palm Springs and other resort markets.
  • No integrated quote system: You can’t be entirely sure what rate an owner is going to quote you. While the system allows owners to publish rates and rate categories, it doesn’t support fancy things like dynamic pricing. As an example of how this might impact you: For Elrod Villa, I use a dynamic pricing system that is integrated to our HomeAway and FlipKey listings. It adjusts prices based on market demand, how close your requested dates are and hundreds of other factors. And it does this every day. I can’t manually go in and adjust our rates on every day. So, the prices listed there are just a “serving suggestion.” They’re in the ballpark, but when you inquire, the quote I send you may be more or less than the rates published on that site (I prepare your personalized quote based on what my dynamic pricing engine suggests to me).
  • No fancy stuff: No integrated trip/cancellation/damage insurance. Owner will hold your damage deposit. No integrated payment system. If you’re dealing with a responsible vacation rental operator these can be non-issues, but caveat emptor applies.

tl;dr department: has a small but growing inventory of vacation rental properties in Palm Springs. It puts you directly in touch with vacation rental owner/operators and, as such, has the potential to get you a booking at the lowest possible cost to you (with potentially more risk).

Was this Article Helpful?

I hope that I’ve been able to provide some useful tips on how to maximize your chances of booking the ideal vacation rental home by giving at least some insight into what vacation rental owners are looking for, and how owners (at least, this owner) think about the various vacation rental search/booking sites.

Did any of these tactics work for you? Did any of these tips help you? Do you disagree with my assessment of the various vacation rental booking sites? Have any tips or questions for me?

Let me know your thoughts by commenting or zap me an email to!

tl;dr department: I welcome your feedback and comments. Did you read this far? Wow, you deserve a bonus. Tell you what: If you’re ever interested in booking Elrod Villa, mention this article when you inquire — we’ll quote you 10% off the rate when we reply to what will surely be an awesome inquiry. You can learn more about Elrod Villa here. Cheers, Keith

Written by

Elrod Villa is a luxury vacation home rental close to downtown Palm Springs with private pool & spa, gorgeous mountain views & sleeps six guests. City ID #1234.

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store