Your Ultimate Guide to Vacation Rentals

Updated June 16, 2020.

Have you started using vacation rentals instead of traditional hotels yet? My sweet husband and I have finally bounded into the 21st century and gotten on board with vacation rentals! Even my parents have been using VRBO for years, and my first HomeAway experience landed my mom and me an opportunity to stay in a Fixer Upper House!

While planning our recent trip to Maui, we had a much harder time finding a good hotel at a reasonable price than we did on the other islands we’ve visited. I knew several people who had stayed in nice vacation rentals on Maui, so we started looking into those. So I decided to write up a guide to vacation rentals including what to look for, what to know, and some things to think about while you’re weighing your options!

Know Before You Go

There are a couple of points I’d like to make first:

No Traditional Amenities

One problem with vacation rentals, especially if you’re used to staying in hotels, is that the amenities you take for granted at traditional hotels may not be included. Your vacation rental will likely not include toiletries or daily housekeeping. Additionally, you may be required to do some cleaning yourself before you leave, such as dishes, laundry, or taking out the trash.

Fees Add Up Quickly

The variety of fees added to the base price of each vacation rental is kind of a lot to stomach right before booking, especially after you’ve been sifting through so many options for hours or even days! The base price you see on the listing is not the price you will actually pay.

The Mailander House Vacation Rental on HomeAway
One positive vacational rental experience for me was
the Bicycle House from Fixer Upper in Waco, TX!

What is a Vacation Rental?

A vacation rental is a personally-owned property, like a house, townhouse, or condo. You will be renting from the person who owns that property, but lives somewhere else. (Air BnB is the exception to this.) Sometimes, the owner lives in another state or another country, so they hire a local property manager to take care of their vacation rental and be the person you can call if there is a problem. This is instead of a front desk attendant like you would have at a hotel. Some other distinguishing factors of a vacation rental are:

A Feeling of “Home”

Because you are living in someone’s home, vacation rentals have a reputation for “feeling more homey” and having more room. You’re renting the whole property instead of only a room as you would in a hotel or traditional bed and breakfast.

A Sense of Space

If you have pets, kids, or a large group, you can probably save some money going with a vacation rental, and it’s nice to have your own space and not be in such close quarters. Because you have the whole home, everyone could potentially have their own room and even separate bathrooms!

Share and Share Alike

A bonus when booking a vacation rental is all the good stuff people leave behind. In the bathroom you might find bottles of sunscreen, bug repellent, aloe vera, itch cream, and more. In the kitchen you might find coffee, coffee filters, spices, cooking oils, condiments, and more in the pantry or refrigerator. Many beach rentals also have beach toys, bikes, kayaks, and other useful, fun gear renters can borrow. The downside is that you don’t know what’s available to you until you arrive!

Spices and coffee filters above the stove and microwave
Condiments and aloe vera in the refrigerator

Where Can I Find a Vacation Rental?

The most popular vacation rental sites and apps are VRBO (Vacation Rental By Owner), HomeAway (as in, your “home away from home”), and Air BnB (see the end of this post for a note on Air BnB), but there are others out there, and more will undoubtedly be popping up in the future!

Fresh flowers from the jungle behind our vacation rental on the Road to Hana.

What Should I Look for When Booking a Vacation Rental?

This is where things get tricky. At least it did for us! With my mom’s birthday trip to Waco, TX, I knew she wanted to stay in a Fixer Upper house. So that narrowed down our search considerably. Our options for Maui, on the other hand, were far more vast! That made our search a lot more complicated. Luckily, you can filter your search by a number of factors, including number of rooms, number of bathrooms, location, kid friendly or adults-only, pet friendly or not, smoking or non-smoking, laundry facilities available, and more.

Narrow Down Your Search

With so many listings and options to choose from, it’s very important to narrow down your search.

  • Price: Because of extra fees that are sometimes not visible until check out, I suggest starting your search with the top price at about 75% of your total accommodations budget; that will reduce the sticker shock when you see the added fees upon requesting your rental.
  • Location: You will not receive the exact address until just a few days to a couple of weeks before your trip, but you can see in which neighborhood or area the property is located. There may also be clues in the listing’s overview or reviews such as “one block from the beach” or “one mile from the airport,” etc.
  • Dates: This will determine which properties you see. Only need a room for two nights? You won’t even see properties with three-night minimums or greater. The more nights you stay, the more properties you’ll see.
  • Number of Guests, Bedrooms and/or Bathrooms: Have a large party of 10 or more people meeting up for your trip? You’ll only see properties that can accommodate that many people.
  • Amenities or Features: Choose the options that appeal most to you, such as hot tubs, beach access, non-smoking, wi-fi, pets accepted, and more.
  • Property Type: This could be an apartment, condominium, single-family home, cottage, cabin, townhome, etc.
We didn’t stay here, but the Magnolia House vacation rental sleeps up to eight! Pro tip: You definitely won’t find this one on a third-party site!

All in the Details

This is where it pays to know what you’re looking for and what your “make or break” rules are.

Nightly Minimums:

Many vacation rentals require a minimum number of nights for guests to stay.

Cleaning Yourself or Paying a Fee

Some vacation rentals require that you run the dishwasher, put the sheets and towels in the washer and run it, and tidy up before you go. Others will do all that for you… for a price. Even if you do pay a cleaning fee, you still may have to do some tidying.

For the accommodation in Hana, Maui, we had to put all used towels and linens in the bathroom, hand wash all the dishes (no dishwasher), tie up and take out the trash and the recycling, and turn off all the lights. Some of that is fine, but I’ll be honest, if I wanted to wash dishes by hand, I would not go on vacation!

The trade-off of staying in a vacation rental in Hana is that we got the Pipiwai Trail and Bamboo Forest to ourselves before the Road to Hana day trippers even started!
More details here: Reasons to Stay in Hana

BYO: Bring Your Own Linens, Dishes, and Utensils

This is a major bummer if you don’t know to look out for it! If you want to book a property that provides linens, be sure to look for that. The same goes for dishes and utensils. Properties are not required to provide those things for you, but many do because they know guests want them. Just check to be sure!

24 Hours to Approve

Generally, owners have 24 hours to respond to your request to book their property. Remember that these people typically have a full-time career, may live in a different time zone, and are only renting their properties on the side. Also be aware that they can deny renting to you for any reason. Here is a direct quote from a property owner who rents on Air BnB, HomeAway, and VRBO:

“There are a few reasons I wouldn’t rent to someone. 1.) Bad reviews from other owners 2.) I want the property for myself during that time 3.) They are asking questions that make me think they could have a motive to do something like a party 4.) If they have a profile picture that makes me think they would be doing drugs 5.) I don’t mind some special request but sometimes guests go extreme and ask for ridiculous things to accommodate them. I usually turn these guest down because I don’t think they will be happy under any circumstances 6.) If they are wanting to put more guest in my house/apartment then permitted 7.) Attitude.”
That’s right! Vacation Rental owners can review guests, too!

Taxes and Fees

All accommodations (hotels, bed and breakfasts, Air BnB, HomeAway, VRBO, etc.) have to charge taxes. Unlike hotels, however, vacation rental fees can vary greatly and really add up! Fees could include cleaning after you leave, service fees the owner has to pay to the vacation rental company, and more, so don’t be surprised when the nightly price you see is far less than what you will actually be paying. I wish all listings would tell you the fees up front so consumers could make a true, apples-to-apples decision. This is a huge turn-off for me with regard to vacation rentals.


Some property owners require you to purchase insurance at the time of booking. I don’t like this at all. My husband and I were one click away from booking a property for 4 nights on Maui, but at the very end of the process we were forced to choose between an $85 non-refundable deposit (on top of several other fees not included in the base price) or a $1500 deposit only refundable at an undefined time after our trip was complete.

We were definitely not paying that. We went back to the drawing board (very frustrated, I might add) and booked with a different property. I am a reasonable person, and I do realize that owners have to take care of their properties, but that huge fee at the very end of the process was entirely unreasonable. If we’d had the choice to opt out of that insurance and something got broken, I would have fully expected to pay for repairs or extra cleaning if required. To charge so much, right at the end is like a slap in the face to responsible guests like ourselves. No thank you.

Towels and toilet paper provided, but in limited quantities!

We Had a Few Surprises…

The benefit of choosing a hotel is that the consumer has just a little bit of power when things are not as expected. With a vacation rental, the owner or property manager has an easier time flying under the radar, and since there is no staff onsite in the majority of cases, you’re sort of stuck with what you get. Here are some examples:

Surprise! Wifi Restrictions

We chose our vacation rental on the Road to Hana for several reasons, one of which was wi-fi availability. We booked two months in advance, and everything was on track. Except two weeks before check in, the owner e-mailed to say we were only allowed to use the wi-fi to check e-mail and we were absolutely forbidden to stream anything or we would forfeit part of our security deposit. We would also be responsibly for causing this property and their neighbors to lose their wi-fi access. Yikes!

Surprise! No Backing Up Photos!

When we arrived, the instruction book on the coffee table also forbade uploading and downloading photos. That’s kind of a big deal for me as a travel blogger! That included sending my photos and videos from the day to the Cloud, meaning I had no backup of those photos and videos if something happened to my phone. Also, no Instagram, which is the primary way travel bloggers interact with their following! I was not thrilled about this, and I probably would have chosen another property had I known that at the time of booking.

These were precious memories and blogging materials I did not want to lose!

Surprise! Stained Sheets!

At our vacation rental in Kihei, we discovered the first morning that our sheets were dirty. Unfortunately for us, we didn’t realize that until after the first night sleeping on them! Gross. So I called the property management company, and after several hours, I ended up calling them again to ask for a new set of sheets (there were no others in the rental).

The woman who cleans the condo let me know she was very inconvenienced to have to come change the sheets, and she insisted the reddish-brown mark was just a stain, and that the sheets had been previously washed and were in fact clean. I guess I believed her, but all I could see was a stain on sheets that should have been clean without a doubt.

Beyond that, the condo in Kihei was otherwise nice enough, and the view and proximity to a beautiful, uncrowded beach were awesome!

View from our condo in Kihei, Maui.

The moral of the story is to keep expectations kind of low. The pleasant surprises will be more pleasant, and the unexpected disappointments will be less disappointing!

A Note on Air BnB

If you’ve read my post Your Ultimate Guide to Accommodations, you know I am not a fan of Air BnB. I’ve just never had a good experience, and I am always reading about negative (sometimes detrimental) experiences of fellow travelers in some of the Facebook groups I’m a part of. I know some people who have had wonderful experiences and saved some money (maybe) using Air BnB, but I cannot in good conscience recommend using this service. I strive to share honest, helpful information on my blog, and that is a 100% honest opinion!

Need more helpful info like this? Check out all my best tips and recommendations on my Travel Planning Page! And you’ll find even more on my Travel Tips Page, too!

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8 responses to “Your Ultimate Guide to Vacation Rentals”

  1. It is very worth information. Thanks for sharing

    1. quickwhittravel Avatar

      Thank you very much!

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