November - January Is The Best Time To Start Airbnb

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Within the past two years of being in the vacation rental industry, I’ve learned that timing is everything in this business. While most people believe that summer is the high season for Airbnb, I’ve found that the best time to actually start your Airbnb arbitrage journey is between November and January. The so-called "slow season" for real estate is, in fact, a hidden opportunity for hosts to land multiple unit deals, negotiate better lease terms, and even get extra concessions.

1. Property Managers are Desperate for Tenants 🏡

November through January is generally considered the off-peak season for tenants looking to move. Most people are settled into their homes for the holidays, kids are in school, and fewer people want to deal with the hassle of relocating during the winter months. But, this works to your advantage if you’re in the market for new Airbnb units.

Complexes with vacancies are under pressure to fill their properties, when units are sitting vacant, property managers become more open to negotiation. You can often score multiple units in the same building or complex because they are more motivated to get them occupied.

Negotiate Concessions 💰

This could include:

• Reduced rent for the first few months

• Free parking or other amenities

• Flexible lease terms 

Many landlords would rather offer incentives than leave their properties empty, so don’t hesitate to ask for concessions, especially during this time!

2. Discounted Homes on the Market 👀

If you’re interested in short-term rentals (STR) for homes rather than apartments, this time of year can be ideal for scoring deals on homes too. Homes that are listed during the holiday season often sit on the market longer than those listed in spring or summer. Why? Because no one really wants to sell their home during the holiday! 

For you, this means homes that remain on the market during this time are often being sold by motivated sellers. Whether the seller is relocating or needs to offload the property for financial reasons, this gives you an opportunity to negotiate better purchase/rent prices or lease terms. Use the slow season to your advantage and get a jump start on the competition, who are likely waiting until warmer months to strike deals.

3. Avoid the Summer Rush ❌

By getting started in the winter months, you’ll also be positioning yourself to avoid the rush that typically comes in the summer. Many people wait until the peak season to start their Airbnb arbitrage business, which means they’re competing for the same properties and often dealing with higher rents and less negotiating power. By acting in the off-season, you can lock in lower rates and better lease terms before demand picks up.

4. Perfect Time for Listing and Prep ⏳

Lastly, November through January gives you the time to set up your units, stage them, and perfect your listings without the stress of immediate high demand. You can focus on optimizing your property for guests—from selecting the right furniture to ensuring the best amenities are in place—so you’re fully prepared for the influx of guests when the high season rolls around. This also gives you time to get a good amount of reviews on your listings, which help with bookings!

If you’ve been thinking about getting into Airbnb arbitrage, the time to start is now. The winter months present unique opportunities to lock in deals, negotiate favorable terms, and prep your units for success. Property managers and landlords are more likely to work with you, and you can build up your portfolio without the intense competition that comes with the summer season.

As someone who scaled to 48 properties in just two years, I can confidently say that these months are a goldmine for host. I have dramatically scaled my company every year during these months - and you should take advantage of this opportunity as well. When everyone else want’s to wait for high season, we dive right in… now!

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Chat soon,

Hailie ❤️