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how to pick a vacation rental
10/02/2018 | by Sheppard Atkinson | Vacation Rentals

The vacation rental industry is the quintessential example of a “niche” market. Navigating a new industry can often be intimidating. Here are the top five insider tips for booking the perfect vacation rental. 

Real estate, hospitality, customer service, property management (and so much more) all combine to create a specific travel experience. If you are willing to step out of your comfort zone, you’ll find something very special about vacation rentals and the hosts that manage them. You’ll form a relationship, possibly even a friendship, with the management team. You will likely feel inspired and welcomed when you immerse yourself in the local neighborhood. These interactions, paired with the quirkiness and attention to detail vacation rentals provide are often the reason guest’s keep returning year after year. In fact, most guest who try the change of pace of booking a vacation rental end up kicking themselves for not doing it sooner – ourselves included!

We’ve gained first-hand knowledge of the industry after managing high-end rentals for over four years. Now when we travel, we implement the following takeaways for every rental we consider. You should too!

Below are some main points to consider for any vacation rental home wherever you find yourself exploring.

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Yes, most online listing sites take a service fee charged to those booking a home, but that’s because they provide peace-of-mind as their main service. Sites like VRBO and Homeaway (along with Airbnb, TripAdvisor and are reliable and safe ways to reserve the best rental for your needs. The top Homeowners pay a hefty annual subscription to advertise on these sites so you can expect the most up to date information. Sites like VRBO and Homeaway gauge rankings through an algorithm. Rankings take into consideration photo quality, review ratings, descriptions, response time, etc. It’s a safe bet to assume that those listings with good reviews and plenty of past reservations (and a broad presence on well-known websites) are truthful and managed by homeowners who CARE.

When you’re browsing among options on Homeaway and VRBO, keep your eyes peeled for that Premier Partner badge. Premier Partners are owners and property managers who have taken a pledge to continually provide the best possible traveler experience. These particular listings meet certain criteria like fair and competitive pricing, up to date advertising, quick response time, honor bookings and much more.

Once you have found a reputable company on a listing website, do your due diligence and Google the company name and location. Most of the more qualified, well-organized vacation home owners and managers will have their own website or at least a facebook page. After you find them off a listing site, you can then contact them directly and save BIG (6%-35+%)! You can explore their full portfolio of properties and get a better feel for their level of service and experience.


Don’t be afraid to message the owner before booking. Actually, it’s encouraged that you do so! This can determine if they’re a good communicator and ensure the property is a good fit. You’re looking for a fast response that is clear, detailed and transparent. This communication will translate throughout your stay, especially in regards to possible issues that may arise. Remember, houses have a mind of their own. Maintenance is needed sometimes.

If it’s not clear in the listing, make sure you ask what’s included in the rental. Inquire if bath towels, linens and paper products are provided or should bring your own. Check the amenity bullet points of more detailed listings for this information on what to ask. If you’re browsing through photos and see towels on the bed or folded in the bathroom, it’s doesn’t always mean the host provides them for free (and it doesn’t hurt to double check)!

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Don’t be afraid to ask for specials or promotions! Your date of travel can have a big impact on how flexible your host can be with the nightly rate. All vacation rentals have  peak and shoulder season pricing variations. Sometimes moving your travel dates as little as a few days can result in a significant discount as well as a reduction in crowds! Often times, especially if the team manages many homes, hosts are willing to discount. This is obviously all dependent on demand and vacancies but never be afraid to ask. The worst that can happen: you get a firm “no, sorry, we can’t do that.”

Also, do not be ashamed to explain the reason for travel. If there is a sickness in the family or if you’ve been displaced by a natural disaster, for example, and need short-term accommodations, hosts will likely be moved by your story and WANT to help your pocketbook out a bit. We just welcomed a family in after a Hurricane displaced them; they stayed for two weeks at more than 50% off the total price. There IS still good in this world, so don’t be afraid to be forthcoming with information that may help the budgeting process some.

Most hosts would be happy to help (if they can). But, do not lie. We can tell…


You don’t want to be cleaning dishes on vacation, so double check for that dishwasher! Amenities like a washer and dryer, ceiling fans, grills with propane, outdoor furniture, high-end appliances and complimentary items are extras that can really make your trip relaxed and add comfort.

If you’re bringing a vehicle, make sure to ask about parking. Each city and town varies in parking requirements and availability. Private parking is a huge perk for many vacation rental properties, ultimately easing the stress for both the homeowner and guests. If you arrive early and the house isn’t ready for check-in, most hosts will allow you to park in your designated space while you wait. This lends the perfect opportunity for a stroll around the area. Grab lunch, site-see and wait for housekeeping to finish making that home perfect for your arrival.

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If you’re booking a vacation far in advance, strongly consider buying travel insurance. Most vacation rental management companies offer this as a completely optional purchase but it could end up saving you money in the long run. Unforeseen circumstances, like a death in the family or a hurricane randomly blowing through during your planned visit can really put a damper on plans. A small upfront fee can save you thousands of dollars and lots of headaches should something arise.

When it comes to booking a house, just like anything else, go with your gut. Life is short so Take the Trip!

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