Finding Your First Vacation Rental


As the economy continues to lag many Americans are discovering the world of vacation rentals. Families in particular are finding that vacation rentals are a much cheaper way to enjoy first class accommodations at reasonable prices. Renters can visit exotic locations and expensive cities for half the cost and three times the space of a traditional hotel. However, despite the perks of vacation rentals, many people have yet to try them out. There are various reasons for this, but one common issue is that the would be first time vacation renter is simply nervous about (or doesn't understand) the rental process. It's true, that when someone books a hotel they basically know what they are buying, a level of stale predictability. With a little homework and due diligence, anyone can find a vacation home that far exceeds their expectations.

This list of tips and tricks will help you, the first time vacation renter, get the right place the first time so you too can start enjoying the wonderful world of vacation rentals.

Vacation Rental Listing Sites

Currently all of the vacation rental listing sites are basically the same. They each have their own color scheme and look but their search functions and features are almost identical. Simply by googling 'vacation rentals' you can find a myriad of listing sites, so, just find one you are comfortable with and you're ready to start searching.

Finding Homes

The hardest part of the whole vacation rental process (and maybe the reason many people don't rent them) is finding properties close to your destination. There are hundreds of vacation rentals in every major city, but if, for example, you searched 'Disneyland CA' on any of the major listing websites you would be given results from San Diego to Santa Barbara and everywhere in between. This search term on one of the larger sites brought back 540 listings. It would take long time to wade through all of these listings. Therefore, if you are traveling to a large metropolitan area like LA, it's best to find the name of the actual city you want to stay in e.g. 'Anaheim' for Disneyland. Unless you are familiar with the area you should start with Google Maps. From there you will be able to see the surrounding cities, attractions, etc. To use our Disneyland example, maybe you want to stay at the beach rather than in Anaheim. By using Google Maps you can see that Newport Beach or Huntington Beach would be great places to start looking for a vacation rental. On the same listing site as above the search 'Newport Beach CA' brought back 111 listings, and 'Huntington Beach CA' brought back 33 results. This is a much smaller list to manage and you know that the properties are all in close proximity to your desired destination.


Once you get your search narrowed to 4 or 5 houses that look good from their locations and pictures its time to start comparing. First, You need to contact the owners directly (this will save you a lot of time!). DON'T bother reading the pages and pages of features, amenities, things to do, etc. With one phone call to the owner you will have all the info you need without reading 400 lines of text. Remember, this is the property owner's business, so they are more then happy to talk to you. Also, you will get a good idea just through your conversation whether or not you want to rent from this person. While you have them on the phone ask them about the amenities, condition of the house, recent upgrades or renovations, if their family stays at the house often, etc. These questions will give you a good idea of the true condition of the house. If the family is there often then most likely the owners keep a close watch on repairs, upkeep, etc. If they rarely use the place then it may need new paint, the yard might need attention, or there may be some other issue associated with an absent owner. A short written list of questions will prevent you from forgetting a question or leaving something important unanswered. Most owners are very upfront so don't feel like you need to quiz them or pry answers out of them, but its helpful to have specific questions that you would like answered.

If you don't see them, ask for pictures of bathrooms and the kitchen. These rooms, more than others, will show you the condition of the home. Look for little details like age of furnishings and bedding. After your phone calls if there are still 2 or 3 houses that look good it simply comes down to the details. Do you want the pool and spa with 2 bathrooms, or the house that only has a spa but 3 bathrooms? These details differ for the party, but the hard work is done and you are ready to book!

Contracts, Fees, Credit Cards, etc

Here is another place the first time renter gets scared. Have no fear, this is the easy stuff! Owners have rented their properties many times and even though its new to you they know what they're doing. Some owners have simple contracts, others have more complicated ones. You should read it through and ask any questions you have. However, a contract will protect you as much as the owner. The owner of a property is in business-they want to rent their home and they want return business. They are trying to provide the best possible experience for you as their guest and will answer any questions you may have. If you are nervous about giving your credit card information know that you are actually safer using a credit card for payment. If you call your credit card company to contest a charge with a merchant, the credit card will support you as their customer, unless a merchant can show total fraud and use of the property on your part.

Security deposits and cleaning fees protect the property, the owner, and you. Generally the cleaning staff are the eyes and ears for the owner. Just follow the outlined rules for the home and you will receive your security deposit back. Be honest if something does break, let the owner know and they will usually be very understanding. Owners are people too and do understand accidents. Although you will be responsible for replacement, it is much easier to deal with it upfront than fight over it later when the property owner does discover the broken item. Again, owners are looking for good customers who love their home, they are not looking to "rip you off", take security deposit money for no reason, or steal your credit card.

If you do find a home is not as advertised, immediately contact the vacation listing site where you found the property, as well as the property owner. Listing sites are also in business and do not want owners listing with them that create a bad name for their site or for the vacation rental industry. They will remove the listing and very well may help in getting your money back. Overall vacation rentals are a very positive experience. Every once in awhile there are small discrepancies but these are few and far between. This is one reason vacation rental use grows each year.


Okay, you've booked your first vacation rental and now its time to go enjoy it! Each year more people are discovering that vacation rentals are the best way to travel, they enjoy privacy, space, and a unique experience every time. With a little work you can find the perfect place for your party and have more fun and relaxation then a hotel could ever provide. So, for your next excursion, remember to book a vacation rental. Happy vacationing!

Co-Founder of Trekadoo - Stewart and his family have been in the vacation rental industry for over 10 years. Trekadoo (beta) is the new way to management your vacation rental. Trekadoo vacation property management software is designed for individual property owners not management companies. To join the beta go to