How to Rent Vacation Homes or Villas

How to Rent Luxury Vacation Homes or Villas Where to find them, who to rent from, what to expect?

So you and your family sit down to dinner to map out this year’s big family vacation. After much discussion, two ideas emerge as the most popular, a vacation to a Caribbean island during winter break, or a vacation in the Italian countryside during summer break. What the family is unanimous about however is that this year, we aren’t doing a hotel!  Tired of competing for the best chaise lounge around a resort’s swimming pool, or standing in line at the breakfast buffet, this year you decide to rent a luxury vacation home.

How to rent a vacation home with wimco villas, villa rentals

Renting a luxury vacation home is easier than ever, and it seems that no matter where you want to vacation, there are beautiful contemporary private homes available to rent…from one bedroom beachfront villas perfect for a couples’ retreat to large estates that can easily handle a multi-generational family reunion. Renting luxury vacation homes or villas also puts you more in touch with the destination, providing a more authentic way to experience the local culture, cities and people.

The decision then comes down to what level of assistance you want or need in finding the ideal home, what help you want with travel planning, and what level of “protection” you are looking for. The options for finding a luxury vacation home rental are many, however not all vacation rental companies, property listing websites or vacation homes are equal.

1) Vacation Home Rental Agencies

A vacation home rental agency is defined as a service company that has direct rental listing agreements with the owners of vacation homes or villas, a reservations staff to help vacationers find the ideal home, and a local customer service staff to assist with the delivery of local services while you are in the vacation home. At one end of the spectrum are companies with one or two receptionists who take reservations for vacation home rentals, with a local office to hand out keys to properties when you arrive. At the other end of the spectrum are companies with dozens of “villa specialists” to assist in finding the ideal house, along with a travel services staff that can set up your flights and rental cars, and a local customer service team on the ground handing the airport meet and greet program, along with a reservations desk for booking local services during your vacation.

Another variable amongst these vacation home rental agencies is their geographic scope of operations. Basically there are two types,  local companies that represent a very local portfolio (vacation homes for rent in Key West only for instance), and companies which represent a more international portfolio of vacation homes (representing properties in the Caribbean and Europe for instance). Agencies that represent vacation homes located outside of the US often refer to those properties abroad as “villas”, so the term “vacation home rental agency” and “villa rental agency” are interchangeable.

A villa rental agency provides their clients (or their client’s travel agents) with a measure of peace of mind (someone else is sweating the details), and protection (they are your advocate should there be an issue with the house once you arrive). The benefit is that you are working with agents who have deep destination and product knowledge, along with local relationships. You can trust the recommendations they make because they have experience dealing with the local property owners, and the local property managers.  Another benefit of working with a top rated villa rental agency is that if something goes wrong, from missing a flight to an air conditioner that doesn’t work, you have an advocate to help you fix it. In some cases that means that they can move you to a different villa if something is not working at the villa your rented – at no additional charge. This is a service that a renter does not get when renting directly from a villa owner. These villa rental agencies earn a commission from the home owner for providing marketing and reservations services, so there is typically no extra cost to you the client for using a villa rental agency.

Examples of highly rated vacation rental agencies with an international yet focused reach include WIMCO VillasAbercrombie and Kent Villas and Asian Luxury Villas. Examples of vacation rental agencies with a strictly local focus include Vacation Homes of Key West, and Harris Group in Maui.

2) Travel Agents

If you are accustomed to booking your business and/or leisure travel through a travel agent, then by all means tell them you want to rent a vacation home, and ask if they have a list of trusted suppliers they can tap into. Most travel agencies keep a list of preferred providers that they recommend all their agents use…that’s the case for airlines, hotels, rental car agencies and vacation home rental agencies. Your travel agent is likely to have a good working relationship with several of the top vacation home rental companies, and they can help you find the ideal vacation home.  These vacation rental agencies have earned your travel agent’s trust, so you can feel comfortable with the homes your travel agent suggests. As with working with a vacation home rental agency directly, typically there is no extra cost to you to use a travel agent when booking a vacation home through a travel agent.

3) Vacation Rental Listing Platforms

These platforms are also referred to as property listing sites. The largest companies in this category like Homeaway, Airbnb,, VRBO and Tripadvisor  have up to 5 million listings. The advantage is of course options. No mater what destination you are looking to rent a vacation home in, these platforms will serve up options…although in some cases the number of available options can be overwhelming. It is important to know that in most cases you will find the same home listed on multiple Vacation Rental Listing Platforms as more distribution (by the home owner, and by villa rental agencies) leads to more rentals. This means there is significant overlap and product duplication across these platforms.

While these platforms list properties, most do not employ staff to provide consultative service to help you choose a vacation rental, nor do they provide any staff to deliver local services. Their role is strictly to provide you with a self-serve market place for finding homes.

The vacation homes listed on these sites can be divided into two groups – homes listed by vacation rental agencies like the ones described above, and home listed by individual home owners directly. As a vacation rental shopper you can research who the listing agent is for each property (usually noted in the “owner information” tab) and decide how much or how little service and protection you want. If you choose a property listed by a vacation rental agency, not only will you get information on that property, but you’ll also be told about others like it in their portfolio. If you choose a property listed by an individual owner, you will get detailed information about that house, but the owner is not likely to tell you about others like it that he or she doesn’t own.

Getting the Best Price

Most of us would love to pay less than the listed price for something, no matter how much we make. Who doesn’t like to share stories of the “great deal” they got on a car by haggling on the lot, or the supper savings they realized by shopping at an outlet store early Saturday morning.

In the vacation world, many of us have purchased vacations at hotels where a special offer landed you a nice savings. Some of you have purchased a vacation at an all inclusive resort, which seems like a good value. The same can be said for flights…if you hunt around, and get your timing right, you can save some money.

vacation home rental chart service vs selection, villa rentals

Renting a vacation home is no exception…you all want to get a good deal. Each property has a publicly listed price posted online. Here is something you may not know that’s critical to understand…The listing agreements rental agencies have with home owners mandates a “One Price in the Market” rule, meaning that a home owner cannot list a house at a lower price directly than the price they provide to a rental agency to list the house at. That’s important to know when you start your search…you won’t find a house listed at multiple prices on different listing platforms and agency sites – each property has just One Public Price across all websites and through all agencies.

Whether you are renting through a vacation rental agency, or from a home owner directly, it never hurts to ask if they can negotiate a lower price for you than what’s listed. Your chances for winning a lower price increase as you get closer to the arrival date. It may also be possible to negotiate a reduced price if you are looking at a vacation rental during an off-peak week.  Agencies have business relationships with owners that give them leverage in some cases, such as mentioning their client is looking at two other properties, so there is little evidence that you can only get a lower price by negotiating with a home owner directly.

Service, Service, Service

Did you know that the same house can be found through multiple agencies, at the same price, and yet the vacationer is offered widely varying levels of service depending on who they rent the house through? At one extreme is the “no frills” model where you book a house, drive to an agency to pick up the key, and you are on your own. At the other extreme are the “consultative agencies” like WIMCO Villas and Abercrombie & Kent that find you the ideal villa, book your flights, meet you at the airport upon arrival and provide concierge service during your stay – both service models can be in effect for the same house – for the same price!

Protecting Your Vacation

You all have been there…flights get cancelled, someone gets sick and can’t travel, a train workers strike shuts down service in a country…and you can’t get to the hotel or resort you’ve reserved. If you miss just one night of your vacation, and you find a sympathetic reservations manager, you might get a one night credit from the hotel or resort…or you might end up paying for that night even if you couldn’t make it.

The same is true for renting a vacation home. If your trip gets delayed or cancelled a sympathetic home owner may give you a refund for one night, or a one night credit on a future stay, however that’s a long shot. If you rented the home through an agency they may be able to bring their influence to bear on the homeowner and get you a partial or full refund or credit. However, the only way to be 100% certain of getting a refund for missed nights is by purchasing trip insurance. There are several reputable companies including Allianz and TravelEx. The cost can be somewhere between 3-6% of the cost of the rental home, depending on the cost of the home and whether you choose to purchase insurance on your flights as well.

The other thing you want to consider if protecting your interests should something go wrong with the home you rented. Imagine that the AC in the master bedroom breaks down two days into your vacation – what are your options? If you rented directly from an owner you should have their contact information, and you can call or email them to ask them to send a repair man. If you rented from an agency, you would contact the person on their local team who was designated as your local contact when you arrived. In either case, it is reasonable to assume that a repair man will get out to the house and fix or replace the unit in a reasonable amount of time.

What if something more dramatic happens? Imagine you arrive on a Saturday and have a peaceful weekend in your beautiful vacation home. Everyone is happy with your selection. Then at 7am on Monday morning you are awoken by the sound of a table saw, then hammering as a construction crew starts renovations on the home next door. If you rented directly from a home owner, and they only own this one home, then they will not be able to offer you an alternative place to stay. In most cases the best they will do is offer some level of discount/refund for the remaining nights in the home as compensation for the inconvenience…leaving you stuck with the noise.

If you rented the house from an agency which has listing agreements with other homes in the area, you may be in luck. The agency could also negotiate a reduced price from the homeowner if you decide to stay in the house, and may even be able to intervene and have the construction crew agree to a reduced work day to provide some measure of relief, however they may also be able to offer you a move to a similar home if one is available. At no additional cost. With an agency you have an advocate, and you have options.

Vacation villa with ocean views in St. Barths, beach house, beachfront villa

Time to Rent a Vacation Home or villa

Now you have all the information you need to move forward with confidence. Whether you are looking for a one bedroom couples retreat on Grace Bay beach in the Turks & Caicos, a five bedroom home on a golf course in Maui, or a sprawling eight bedroom villa in the countryside of Italy, you now know what your options are for finding the ideal property for your vacation, and creating a memorable experience.

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