Gladori

Planning a villa trip for a big family or a group of friends usually means a dozen browser tabs. Rental company listings are written to sell a house, and each company lays them out differently, so comparing two places gets tiring fast. Gladori reads those listings and rebuilds each house as a page in one format: its size, where everyone sleeps, the staff, and the price for a stated stay, with fees and taxes when the company publishes them.

It also adds things a listing rarely gives you. There are road times from the house to the airport, beaches and shops, calculated from map data. For homes by the water it gives the distance to the sand and says whether a road runs in between. Each page also carries questions worth asking the company before you book, such as whether the pool is heated or how often housekeeping comes.

The site lists 608 homes in five destinations. St. Barts has the most at 313, followed by Barbados with 160. Turks and Caicos has 78, Jamaica 47 and Anguilla 10. You can filter for beachfront houses, staffed houses, a private chef, or six bedrooms and more for large groups.

This is the top of the market. Destination pages start from $843 to $3,309 a night, and the featured houses on the home page run from about $6,000 to $40,000 a night with fees and taxes.

Gladori's data page is useful even if you never rent a villa. It publishes numbers for trip planners and writers, each with its method, sources, a date and a CSV file, under a CC BY 4.0 license.

The sets include hurricane odds by island from 60 years of storm tracks for 21 destinations, sargassum seaweed by month from satellite data since 2018, and runway lengths at 93 Caribbean airports. A villa price study uses quotes for 563 villas and puts the median at $3,401 a night with fees and taxes. Another finds the same villa costs a median 64% more in Christmas week than in mid-January, which is handy to know before you pick your dates.

One limit is stated on the about page. The listings come from a single company, Top Villas, read on October 31, 2026, and the photos are credited to it. So the catalogue is only as broad as that company's.

The site is free to use, and its disclosure page is specific about the money. Links to a rental company can be affiliate links, and if you book, the company can pay Gladori a commission. Requests sent through its forms are passed to rental companies, which can pay for the request. Gladori says it only shows homes from companies with an affiliate program, so not every home in a destination appears. It also says commissions don't set the order of listings, and that no sponsored placements were on the site as of November 4, 2026.

You pay the rental company the price it sets and book under its terms. Gladori adds no fee and never takes a payment.

Gladori is run by Presagio Group, and by its own account no rental company or booking platform owns it. The privacy policy, updated November 8, 2026, says a trip request is shared with rental companies only after you tick a box, and that requests and messages are kept for 12 months and then deleted. If you're gathering a family or a group for a Caribbean house, it's a calm place to start comparing.