Updated: December 2017
Caribbean Villa RentalsA trip anywhere in the Caribbean will set you back some serious money. Many of the islands of the Caribbean are small with few hotels, and the hotels tend to be fairly expensive. So when planning a big-bucks trip, many tourists opt for renting a villa instead of packing themselves into a tiny hotel room. Villas come in all shapes and sizes, with price ranges to match. If you are planning a reunion or a trip with extended family, sometimes a villa rental is a great option, giving you common living space to stretch out in, often a private pool, and always dramatic views (its tough to find spots with "bad" views in the island paradises here!). We spent a honeymoon trip in St. John's, US Virgin Islands a few years back, and we opted for renting a villa high on a hill overlooking Cruz Bay. It was about a 10 minute drive up a windy road to get there, but the home was spacious and comfortable, private infinity pool and hot tub, quiet, peaceful location -- everything you need with beaches and restaurants just a few minutes drive away when you feel like venturing out. In this guide, we will share our Caribbean villa rental experience and take a look at the best sites for finding a villa online - enjoy!
Map of Caribbean IslandsBefore you get too deep into planning your Caribbean vacation, it helps to have a map showing all the names and locations of the Caribbean islands -- all the names and nationalities of these little islands can be confusing, so keep referring to this map as you do you research. Click here to open a map of the Caribbean islands in a new window. As you can see, the lower tip of Florida is the orange piece at upper left. The Bahamas are off to the southeast, while Cuba is the biggest island in the Caribbean south of Florida, with Jamaica just below it. From here we will swing clockwise down and around the island chain that makes up the rest of the Caribbean. Hispaniola is the 2nd largest island, right in the middle of this map, split into 2 countries, Haiti to the west and Dominican Republic to the east. Haiti is the poorest country in the Western Hemisphere -- chances are you won't be vacationing here. Next comes Puerto Rico, a US possession and easy place to visit, as are the US Virgin Islands (USVI, which includes St. Croix, St. Thomas, and St. John) not far off to the east. The British Virgin Islands (BVI, which includes Tortola and Virgin Gorda) lie to the northeast from the USVI. Next comes Anguilla, St. Martin, St. Barthelemy, and St. Kitts and Nevis. Then Antigua and Barbuda, Monserrat, and Guadeloupe. Then we find Dominica and Martinique and St. Lucia, St. Vincent and the Grenadines and Barbados, and Grenada. Aruba sits off the coast of Venezuela, right in the center of the page, an inch from the bottom. When it comes to villa rentals in the Caribbean, some of the most popular villa locations are St. John, Barbados, St. Martin, Tortola and Virgin Gorda, Cayman Islands, and Jamaica, though you can find accomodations on most of the islands.
Renting a Villa in the Caribbean - What to ExpectWhen you rent a villa, it really is just a fancy name for a home. Instead of staying in a cramped hotel room, you will have a little (or HUGE, depending on how much you spend!) house with bedrooms, living room, kitchen, patio, decks, etc. Almost all rental villas in the Caribbean feature private pools and hot tubs as well -- after all, this is the tropics and people come for sun and water. The main benefits of renting a villa are privacy and space. But remember, since you will be staying off a residential road at a home, you won't have room service, daily maid service, or a concierge desk. You also don't have the security of being in a fully staffed building (though these islands are small, everyone knows everyone, and violent crime against tourists is almost unheard of). So if you require non-stop pampering and service from a resort staff, staying in a villa is probably not for you. But let's say you and your family are planning a multi-generational trip with the grandparents and siblings - would you rather stay in 4 different hotel rooms and have to constantly plan interactions and together time, or stay in a big 5 bedroom villa complex where everyone where everyone enjoys the decks, pool, kitchen, and living room together? So that's your first decisions - is a villa right for me or am I more of a hotel/resort person. If you decide you do want to rent a vacation villa, decide which island you want to vacation on, and then comes your two major decisions. The first is - how do I select a villa rental company to see what's available? And the second is - which villa will I actually rent? You'll find a lot of villa rental agencies and sites when you search the web, and you'll soon discover something else - you'll find a lot of the same actual villa properties offered by multiple rental agencies. What gives?
Keep in mind that these villas are the private homes of regular people (OK, not regular, but wealthy people who have rental property in the Caribbean!) -- they are not hotel-owned properties or anything else. And these homeowners make their homes available for rent and list them with different rental companies, just like a home for sale can be found by any real estate agent you choose to work with. So it comes down to finding a rental company that you can trust, that provides you with as much information as possible, in terms of photos, virtual tours, in depth description, and maybe even comments from prior guests to help you make the right selection. When we went to St. John, we went with DestinationStJohn.com - they specialize only in properties on St. John. But most importantly, they live and work right there on the island, and they meet you at the dock when you arrive to help take you up to your villa and get you set up. (We had a great experience with them and recommend them if you are going to St. John - they list properties like ). So its nice to know that when you arrive at this far-away, exotic locale, there are real people there that can assist you if there are problems or you need help with something, like just finding your way to the villa in the dark. So consider that first -- is someone from the rental agency a local person on the island, or who is there to assist me? Secondly, you'll want to check out the website they have to offer to see how many villas they offer to choose from, what their availability is, and what kind of pictures, descriptions, virtual tours, etc. they offer to show the properties. And you'll want to read the descriptions and look at the pictures carefully - we've seen a lot of listing with things like "upscale condominium complex" - condos aren't villas!