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Your Ultimate Guide to Vacation Rentals


Have you started using vacation rentals instead of traditional accommodations 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 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.

The problem with vacation rentals, especially if you’re used to staying in hotels, is all the options you may be expecting that may not be included. And 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 sifting through so many options! 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!

The Mailander House Vacation Rental on HomeAway

What is a Vacation Rental?

A vacation rental is a personally-owned property, like a house, townhouse, or condominium. You will be renting from the person who owns that property, but lives somewhere else. (Air BnB is the exception for this.) Sometimes, the owner lives in another state or another country, so they hire a local property management company or someone locally to take care of the property and be the person you can call if there is a problem–instead of a front desk, 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 space, since 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 (with thin walls) with lots of people you don’t know.
  • Share and Share Alike: A bonus when booking a vacation rental is all the good stuff people leave behind–almost full bottles of sunscreen, bug repellent, aloe vera, itch cream, and more. Often you’ll find coffee, coffee filters, spices, cooking oils, condiments, and more in the pantry and refrigerator. Many beach rentals also have ocean toys, sometimes bikes, and other useful, fun gear renters can borrow. The only 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

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. However, our options for Maui 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, pet friendly, smoking or non-smoking, laundry facilities available, and more.

Narrowing Down Your Search

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

  • Price: This is a pretty important factor and can really narrow down your search! You will automatically see all price ranges, but you can easily change this to fit your budget. 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: It’s true what they say: location, location, location! Want to be more secluded? Or do you prefer to be close to the city center? Or maybe you want to be right on the beach. Or maybe you want to get a better deal and don’t mind walking or driving to the beach. Think about what you’re willing to pay versus where you’re willing to be located. 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: 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.
  • Number of Bedrooms: You will only see properties with the number of bedrooms you choose or greater.
  • Number of Bathrooms: You will only see properties with the number of bathrooms you choose or greater.
  • Amenities or Features: There is every number of amenities combinations, so choose the options that appeal most to you–hot tubs, beach access, non-smoking, wi-fi available, pets accepted, and more. Options vary by vacation rental service.
  • Property Type: This could be an apartment, condominium, single-family home, cottage, cabin, townhome, etc. Think about your preference and what might meet your needs best. If you have kids or pets or like to listen to loud music when you’re getting ready in the morning, a traditional house, cabin, or cottage may be the place for you so you have lots of space and you’re not sharing walls with other guests. Don’t need a lot of space but prefer a view from a high floor? Look into condos and apartments.
We didn’t stay here, but the Magnolia House vacation rental sleeps up to eight!
All in the Details
  • Nightly Minimums: Only staying one night? You will have the fewest options. Many vacation rentals require a minimum number of nights for guests to stay. When you don’t have a full-time hotel staff, it’s hard work to clean and prepare a whole house or condo every night for new guests, especially if you live in another state!
  • 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 fee that can vary quite a lot. And even if there is 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, I would not go on vacation.
  • BYOL — Bring Your Own Linens: 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 and are only renting their properties on the side, so be understanding that they may not be able to get back to you immediately. 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.”
  • 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.
  • Insurance: Some property owners require you to purchase insurance. 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 undesignated time after our trip was complete. Both were to be paid at the time of booking, and there was no way to opt out of either of these additional fees. We went back to the drawing board 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 complete surprise at the end was entirely unreasonable. If we’d had the choice to opt out of that insurance, I would have fully expected to pay for repairs or extra cleaning, but 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!

Some Surprises

The thing about hotels 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:

  • 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 not allowed to stream or we would forfeit part of our security deposit and cause this property and their neighbors to lose their wi-fi access.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 also meant no 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. That also meant 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.
  • 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 property). The woman who cleans the condo was very put out that she had to come change the sheets, and she insisted the mark was just a stain, not that the sheets had not been previously washed. I guess I believed her, but all I could see was a stain on sheets that should have been clean without a doubt.
  • Alternatively, the condo in Kihei was otherwise nice enough, and the view and proximity to a beautiful, uncrowded beach could not be beat!
View from our condo in Kihei, Maui

The moral of the story is to keep expectations 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!

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