The History of Renting a Villa in the Caribbean

Generating Media has a deep respect for five key people who set the stage and developed the concept of short term rentals in the Caribbean. This is long before Airbnb, HomeAway, and VRBO. They actually did the “heavy lifting” to make this option available.

People have for years thought about owning a getaway home in the Caribbean. White sandy beaches, crystal clear waters, and plenty of year-round sunshine were a far cry from everyday living. With the invention of air conditioning made this dream more of a reality.

The villa rental option came as a result of potential owners reviewing the costs of ownership, property management, and utilities. The real estate companies on the various islands needed to provide services long after the sale as the owners were only going to use the property for a rather limited time during the year. The owners needed to have someone clean the pool, take care of landscaping, and overall maintenance of the property. Add this cost to the selling price and it was often far more than most wanted to spend. The real estate companies encourage the owners to rent out their properties short term to help offset these expenses. This option played a key factor in potential owners deciding to purchase a property.

The Challenge of Renting Your Villa

The huge challenge for the real estate companies was to generate short term weekly rentals for the buyers. This put a lot of stress on the real estate companies as the property owners were always eager to have more rental revenue.

Before the internet, it was a logistics nightmare to gather and distribute the villa rental content. It was a world of publishing catalogs, which would go out of date the moment they were published. Catalogs were expensive to produce and mail. In addition, who would the catalogs be mailed to? The quality of the photographs was marginal. Managing the relationship with the property owners, establishing the pricing rental structure, controlling the availability calendar, and keeping the information and descriptions accurate was an on-going challenge that never ended. Terms and conditions such as deposits, final payments, and cancellation fees all had to be established and communicated to potential renters.

Sibarth Real Estate & Villa Rentals

Generating Media was fortunate to work directly with the pioneers of the villa rental travel product in the Caribbean. Roger & Brook Lacour established the gold standard in the villa rental business as they created Sibarth Real Estate & Villa Rentals on St. Barts. If you wanted to rent a quality villa and be taken care of at every level during your experience, Sibarth was the “Go-To” villa rental company. Roger & Brook virtually developed the brand of St. Barts as it is known today. They greatly influenced the personality and spirit of the island. Sibarth Villa Rentals is now run by Roger & Brook’s son Ashley and his wife Kristina.

Carimo Real Estate & Villa Rentals

Roger’s brother Francis Lacour and his wife Nicole created one of the best real estate and villa rental companies on the planet called Carimo Real Estate & Villa Rentals. They could have had hundreds of rental properties on both the French and Dutch side of St. Martin/St. Maarten, but they created a country club atmosphere for their inventory. Their quality requirements were extremely strict and well managed. It was rare to have issues for clients staying in a Carimo villa rental. They also had one of the highest and most consistent occupancy rates of all the islands. The Carimo Villa Rental product brand was something every guest could count on to be of high quality no matter what the price point. Francis and Nicole sold Carimo Real Estate and Villa Rentals to Luxury Retreats, which was later purchased by Airbnb.

McLaughlin Anderson Luxury Villas

The US & British Virgin Islands was offered by an incredible person, who owned an operated McLaughlin Anderson Luxury Villas. She ran a very tight ship. Her attention to detail was the best in the industry. Her efforts were exhausted to make sure all the details, features, and amenities were accurate. Every year she published the “Bible” of the villa rental inventory for the US and the British Virgin Islands. It was easy to follow the catalog with professional photographs and detailed descriptions. Nancy sold McLaughlin Anderson Luxury Villas to a company called Beautiful Places.

It was a great lost to the fabric of the villa rental industry when these individuals left the industry. The villa rental industry could learn a great deal by studying what made these people successful.