Negotiating your vacation rental property price

Almost everything is negotiable, including the price of your vacation. I know this because I’ve managed a vacation rental property since 2012, and have rarely refused a discount to anyone confident enough to bother asking! You may wonder why I’m using the word “negotiation” instead of the phrase “asking for a discount.” In most of these interactions, you’ll be front-loading your entire strategy instead of saving additional tactics/reasons for later. But, sometimes, there will be a back and forth with an owner, with multiple opportunities to settle on a price or arrangement. You’ll want to be prepared for either scenario.

Guests that negotiate are usually affiliated with the following groups: military, teachers, healthcare workers, first responders, and seniors. [My beach rental is dog-friendly, so I add renters with senior dogs to that list.] But you don’t need to belong to a particular group to ask for a discount. Any reason could appeal to a homeowner. Are you in town for a wedding? Running a marathon? Attending a music festival? Why not ask–you’ve got little to lose!

Though the intensity may differ from person to person, you can be sure that everyone you meet is driven by two primal urges: the need to feel safe and secure, and the need to feel in control. If you satisfy those drives, you’re in the door.

Chris Voss, Never Split the Difference: Negotiating as if Your Life Depended on It

Before you negotiate…

Do your research: Consider time of year and what is peak-season and off-season for your location. I don’t particularly need your sale during the busy season because I have a line of renters competing to pay full price. I am more likely to give discounts during off-season. At my particular beach, this is October through March…but it depends on the region. What is considered off-season at your location may surprise you.

Consider experience and culture: Some property owners may not consider themselves business owners, or may be new to ownership. Some can get very attached to their property and consider negotiations or requests to be an insult.

Consider cultural norms when renting internationally; the tone of your message may be received differently depending on where in the world you are going. If your destination is in a developing or recovering area, this rental could be the owner’s only job, or times could be rough.

Ask yourself, “Is this fair? If this were my house, would I consider it fair?” The owner may have costs you haven’t considered and may not be making a fortune. Sometimes houses only pay for themselves and don’t make additional income. That’s not your problem, but it’s on the mind of the owner when they consider your request.

Know that pricing is complex: When owners calculate prices, they take many factors into consideration: property age and condition, time of year, recent upgrades, personal life changes, current events, local concerns, supply chain, and weather [this list is definitely not exhaustive].

Know that even “by owner” property owners perform frequent, in-depth comparisons to nearby properties when finalizing pricing for a season (similar to analyzing “comps” in real estate). Some vacation rental platforms even offer this service to their owners in an effort to improve profits for the owner and the rental platform. In the past, I’ve considered features as granular as wood paneling, granite countertops, and kitchen extras (like a nice blender) into comparisons and pricing adjustments. This means that if a property needs updates and doesn’t offer amenities similar to its neighbors, the owner may have to lower their prices to make sales. They may be unwilling or unable to offer you a discount.

When thinking about your negotiation strategy…


  • Be kind. There are always real people behind these transactions, even if the property is managed by a rental company and not the owner.
  • Be flexible. Owners are usually willing to discount longer stays, because that means fewer/less frequent cleaning fees and management time spent. Some owners will also discount stays that are a result of a last-minute cancellation or around a holiday that’s not usually a travel holiday, so keep an eye out for those. They’re typically featured properties, or high up in search results due to the all-powerful algorithm, and the “boosts” that are available on the back-end to owners.
  • Know your worth. Do you have anything to bring to the table in your message to the owner? Things that could appeal to me as a property owner are: you’ll be checking in later than usual, you have great ratings from prior stays, your group is very small, or your activities will keep you out of the house most of the time. All of these factors mean less risk, wear and tear, cleaning, and utility and resource usage. 
  • Sell yourself. How will you set yourself apart from the many other messages received, and be authentic while doing so?
  • Think about whether your reason is fair or logical. Trying to get a discount just for the sake of getting a discount may not appeal to an owner or even register with them. For example, I have declined a couple of requests (ever) for discounts on last-minute booking requests during peak season. Renters do stalk houses for openings, and they also don’t understand their competition (not their fault). They aren’t doing an owner any favors because that open spot will get filled. Peak season booking chaos can be compared to listing something for free on Craigslist or Facebook Marketplace…RIP inbox!


  • Come to the table with expectations or entitlement. You may have a slight upper hand since they want business, but you’re not that valuable (unless it’s the off season). Your plan always has potential to fail.
  • Be aggressive or demanding (at least in the US). Avoid phrases like “lowest price” or “best rate” which suggest that the owner is being somehow dishonest with you.
  • Use politics, religion, or social issues to get what you want; unless you know how your stance will be received. Even then, it’s easy to see through these tactics. 
  • Overshare. Be honest and cordial, but don’t show all of your cards, as the homeowner may not like something you divulge. Biases exist, whether conscious or not.
  • Ask if you can clean the place yourself to avoid a cleaning fee. This is always a no. Having a guest “clean” and/or do laundry introduces so many risks. Just…no. Often a team of professional cleaners services the property quickly between guests. To do it right, you’d be giving up almost a full day of your vacation time and have to get your other guests on board with your plan.
    • Note that this refusal exposes a fallacy, loophole, whatever you want to call it. Asking to waive a cleaning fee is a hard no, but would actually cost the owner hundreds of dollars less than a 10% discount on a week-long stay during peak season. This is a good example of why your strategy is psychology…you are appealing to human emotions like any good negotiator.

How to craft your message

Negotiating techniques are generally the same no matter what the stakes are. At the end of the day, you’re simply leveraging human nature to your advantage. As a homeowner, I absolutely DO want my house to be safe, secure, and well cared for. And I don’t want to be bullied by a renter.

When writing your initial message to a homeowner, personalize your message. Provide a brief, clear description of who you are and who will be staying at their property and why. No need to write a novel; a small paragraph or less will do. Compliment a feature of the home, and sell yourself in an honest, humble way. Here’s a sample message you can customize:

Hello homeowner (use name if available),

My group will be in town for the local festival, and your property seems perfect for our needs. We are three women in our 40s who can’t wait for a weekend away to catch up. We are thoughtful renters who are quiet, considerate, and clean; and I have five-star reviews on VRBO. Since our group is small, we won’t be using all of the bedrooms in your cabin, but we will be enjoying coffee and the view from your beautiful balcony. Two of us are nurses, and we were wondering if you offer a discount for healthcare workers. This trip is a much needed reward to ourselves after a tough year. Thank you for your consideration!

By now you might be thinking that all you have to do is be nice.

Yep. That’s really about it. It doesn’t work in all negotiation situations, but for this one…it’s that easy. Here’s where the stock phrase “you’d be surprised” is incredibly applicable. My last “one weird trick” knowledge for you is that half or more of renters/bookings don’t send me any message at all with their booking. They don’t acknowledge my humanity by even saying hello. And of the messages that do come in, many of those are brusque, rude, entitled, or unintelligible. Maybe they just don’t understand that there’s a human on the other end of the line, and that’s understandable.

Even if you don’t care to negotiate and all you want at the end of your stay is a good rating, you gain a huge advantage simply by dropping a post-card sized bit of info and a greeting.

Let us know if you have ever negotiated a vacation rental price successfully, and how you did it! 


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