How to Pick the Right Villa for your Family Vacation

When you start searching for villas for your family vacation, there are so many that seem amazing.   But before you get your heart set on one particular villa, it is best to do some preliminary research and thinking about what is important to your group.   Thorough research can help you find the perfect villa for your group and result in a better holiday.  A property with the features that are right for you can make the difference between the trip of a lifetime or a week filled with complaints and regret.


STEP ONE:  What are the basics for your vacation?

First, all of this advice assumes you have already made several decisions.
Where you are going?      While specific is best (within 10 miles of Florence, on the beach near Cancun/Playa del Carmen, or within an hour’s drive of Montego Bay airport), you can still be as general as a Greek Island with direct flights from Athens or a ski house in Utah.

What time of year you are going?     Again, specific dates work best, but if you are flexible, such as, “anytime in February or March,” you have probably narrowed it down enough.     Timing is important so that you can see if you will be falling into high season or low season prices.

-How many people are going/group composition?    This will dictate the minimum occupancy needed in a villa.


STEP TWO:  What are common options for your location?

Next, it is time to do some preliminary research.       If you are familiar with villa options in your target locale, then you can probably skip this step.  But even 20 minutes of internet research will help you understand the types of villa rentals and options that are available.   I would recommend visiting the website of at least one rental agent and doing either an airbnb or HomeAway search.     Pay attention to:

-The cost for rental properties of the size you need and the time of year required.  Make sure this is in line with your budget.

-Are homes located within resorts, private communities, or are they stand-alone?

-What types of options are available for your destination?    Are many villas available fully staffed or is just weekly housekeeping offered?    Are villas located beachfront/waterfront or are all the beaches public?    Are rentals available within the city center or are you going to be in the countryside/suburbs?        The features that are common for a villa rental in Barbados are likely quite different from those in Santorini.

-Are  you required to book a minimum number of days? Or do they only do weekly rentals?

If you are planning on booking through a villa agent, this is a discussion that you could have with them, as they are likely to be able to describe the options that are frequently available in their collection of properties.


STEP THREE:  Make your list of priorities and nice-to-haves

Now that you understand what options are common, you can make an informed list of priorities and nice-to-haves for your vacation.

An example for a ski house vacation might be:

4 en-suite bedrooms Sauna Balcony/outdoor space
Hot tub View of mountains Game room
Walking distance to slopes Great fireplace Proximity to restaurants
Sledding hills for kids Big kitchen


Whereas, if you are prioritizing for the Dominican Republic, your list might look like:

Sleeps at least 12 Private beach Game room
Heated pool suitable for kids Big yard Being part of a resort
1 hour drive from Punta Cana 2 master suites Proximity to restaurants



If you are really type-A, like I am, you might make a spreadsheet of all the features that are must-haves and nice-to-haves so that you can make a detailed comparison of all your options.   I have attached one of mine that compares three villas in Jamaica as well as a blank worksheet that you could use to compare villa options..

When I am looking for a villa for my extended family, I try to ensure that we have plenty of two things: enough space for everyone and access to lots of activities.  I believe that even with the most close-knit group, the vacation will be better if there is a variety of activities for everyone to do and everyone has adequate personal space.   And I don’t just mean that all the bedrooms are awesome and luxurious, but also making sure there are multiple common areas so that everyone does not have to be together all of the time.

STEP FOUR:  What meets your needs?

If you are working with a villa agent, you can give them your list of priorities and they should come back to you with a list of options that might work for you.  If you aren’t using a villa agent, then you want to conduct an in-depth search by looking on airbnb, HomeAway, VBRO, and rental agency websites.    You may also be lucky enough to find articles recommending certain villas at your destination.   Check out the details for all the properties that meet your needs and pick 2-3 that you think would be great for your holiday.  This becomes your short list for negotiations and second opinions.

With your short list of villas begin to search the web for reviews from previous visitors.  Compared to hotels, which might have hundreds of guests per night, finding villa reviews can be difficult.    Check out TripAdvisor, but also search the web for other places where the villa may be mentioned.  Blogs, like this one, can be a great source of detailed information on a villa or property.  This is particularly important if you are not planning on renting through a villa agency.   Cross off any villa rentals that have reviews that cause you concern.


STEP FIVE:   Secure your booking

Hopefully at this point you still have 2-3 villas with which you would be happy.  Contact the villa owners or a rental agency to ask your remaining questions and confirm availability and pricing.   I often have a number of nagging issues, the answers to which could make the difference to whether or not I am still interested in a property.   A discussion with the owner or villa representative who has been to the property can usually resolve these matters.  You may find that once you get your questions answered you are no longer interested in a property, which is why it is good to go into this stage with several options.

Once you have determined your first and second choices,  make an offer for the time you want.  If you are travelling in the off-season, you may also be able to negotiate a discounted price (up to 30% off listed rates depending upon the time of year and market conditions).   If you are genuinely open to multiple properties,  your likelihood of getting the owner to agree to a discount is much greater than if you are travelling at peak season, especially if you mention that you are still considering other villas.

At this point you will be expected to sign a rental agreement and pay a deposit, often about 30% of the rental price.  The remaining balance is typically due in full 60 to 90 days prior, although this varies by property.  Be sure to read the fine print so that you know when the payments will be due.   After the contract is signed and your deposit paid, it is time to relax and look forward to your amazing villa vacation!


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