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Renting in the Caribbean

When people think Caribbean, assumptions abound about what travel is like. All inclusive resorts. Packaged tours. Little cultural experiences outside the walls of these mega-resorts. Basically the opposite of independent travel, which is what we’re all about at BootsnAll.

Traveling to the Caribbean doesn’t have to be like that though. There are plenty of other options to have an indie travel experience on most all Caribbean islands, and it all starts with accommodations.

You don’t have to stay in a resort. You don’t even have to stay in a hotel. A great way to take charge of your trip and itinerary is to rent a house, condo, or apartment during your trip to the Caribbean.

Benefits of renting

Rental properties are popping up all over the world, and this option is quickly becoming popular for travelers who really like to dig into the local culture and get something more out of their trip than simple relaxation (not there’s anything wrong with that). In an area like the Caribbean, where resorts are the norm, it’s refreshing to get out of the gates and be able to interact with the local people.

The Caribbean is a beautiful area of the world, and many independent travelers don’t think of it as a destination because of their preconceived notions. There are some amazing rental properties available that could completely change your perception of islands like St. Thomas, Jamaica, and the Dominican Republic.

Price is often touted as a benefit of heading to an all inclusive resort, but with a rental, it’s possible to get by for even less money than staying in a resort. If you or someone traveling with you likes to cook, money can be saved by shopping for food and making your own meals. Markets are often the best place to truly understand and learn about the culture you are visiting, and taking a trip to the local markets each day can be an experience in itself (and it’s free!).

If you’re the type of traveler who has stayed in resorts in the past but still enjoy getting out and exploring the country you’re visiting, you can save quite a bit on transportation costs by staying in the city instead of on the outskirts of town, where many resorts tend to be located.

Rentals also give travelers the added benefit of options. Even if the mega-resort has 5 or 6 restaurants, staying in a city can provide you with many more dining and entertainment possibilities. If you end up not liking the food at a resort, you’re kind of stuck.  If you are renting and have a bad meal at a local restaurant, you simply choose another place next time out.

Where to go

Puerto Rico

Puerto Rico is one island in the Caribbean that is not littered with giant, all inclusive resorts. There are plenty of massive hotel chains, but there are also plenty of rental opportunities. Traveling to Puerto Rico is unique compared to many other Caribbean islands in that it’s quite easy and safe to rent a car and explore the entire island. Renting a house, condo, or apartment along the way is a great way to see what may soon be the United State’s 51st state.

What to do:  If you like the outdoors, then Puerto Rico has you covered.  Scuba diving, snorkeling, hiking, ziplining, biking, fishing, surfing, and golfing are just the tip of the iceberg.  Not to mention that Puerto Rico has the only rainforest located in the United States.  If you’re a beach person, then head to the islands of Vieques and/or Culebra for some crystal clear waters and white sand beaches.  If you like cities, then San Juan is the place for you.  This colonial city is perfect for photographers, and Old San Juan is easily walkable, with some top notch restaurants littered about the city.

Price: Travelers looking for rentals in San Juan, Puerto Rico can find them for as low as $50USD per night, as high as $450USD, and everywhere in between. Head to the island paradise of Vieques, and it’s possible to rent a place for as little as $55USD per night, or if you are one of the lucky ones who just won the Powerball last week, you can spend $3000USD per night for a 6-acre estate.


Jamaica is an extremely popular spot for travelers to the Caribbean, but many have a false assumption of safety within the country.  Many fear staying outside of resort walls. While it’s always important to exercise caution no matter where you are (even at home), Jamaica is largely safe for those travelers looking to get a different glimpse of the island than most people get, provided you use some common sense. If you’re looking to get away from it all and find the seclusion that’s simply not possible at a resort, then renting is the way to go in Jamaica. There are plenty of cottages and houses nestled in the foothills and near smaller towns that tourists may not typically visit.

What to do:  So many people come to the Caribbean for the beaches and ocean.  If you’re an avid diver (or want to become one), then check out some of the nearby reefs at Runaway Bay and Ocho Rios.  If you’re a coffee lover, then head to the Blue Mountains to try some of the best java in the world. If rum is more your thing, then tour the Appleton Rum Estate, where you can experience the production process of their rum and learn about the unique distillation process in their 200-year-old pot stills.  One of the benefits of traveling to Jamaica is how much different it is than the rest of the islands in the region.  The blend of Caribbean and African cultures makes Jamaica stand out, and often some of the best experiences come from conversing with the locals or stumbling into a nearby bar for some music.

Price: Find an apartment or condo in Jamaica for as low as $45USD/night. If you have a higher budget and want to pamper yourself, then stay in many of the amazing homes available, some for as high as $11,000/night. Of course there are many options in between, with a good number of places being available for under $100USD per night.

Virgin Islands

Both the British and US Virgin Islands provide unique experiences for travelers to the Caribbean. St. Thomas is a major cruise ship port, so keep that in mind if you are planning an indie trip here. Cruise ships don’t arrive every day, so if you are looking to avoid the massive crowds they bring, you may want to plan your trip around them.

A quieter alternative is nearby St. John, especially if you rent. Two-thirds of the island is a National Park, and the world class beaches make this a prime spot for beach bums. There are some amazing rental properties for all budgets here, and if you want to get away from it all, consider getting a place high up on the mountainside.

Tortola, a British Virgin Island, is about 60 miles from Puerto Rico and about 20 from St. Thomas. Like St. John, Tortola is a great place to come for those who like the beach. There are also other outdoor activities to be had, like hiking in The Sage Mountain Park, which has the tallest mountain in the Virgin Islands.

What to do:  If you’re heading to the US Virgin Islands, each has its own highlights.  St. John is the place to go if you’re an outdoorsman.  With two-thirds of the island as a national park, this is the least developed of the US Virgin Islands, and it’s the easiest place to strap on some boots and head out exploring.  If fishing is on your trip itinerary, think about chartering a boat and head out for some deep sea fishing, a great way to spend a day.  St. Thomas is a shopping mecca, so if you plan on bringing back some souvenirs and gifts, then this is place to go (just try to visit on a non-cruise ship day).

The British Virgin Islands boast more than 40 different islands to whet your appetite.  Tortola is the most popular, and you can head up into the mountains or chill at the beach (or both).  Snorkeling and scuba diving are extremely popular here with the crystal clear waters and abundance of underwater activity.

Price: Rentals in the Virgin Islands can be a little pricier than other Caribbean islands, but budget travelers can still make it happen here. St. Thomas has a few places around $50-$70USD/night, but expect to pay closer to $100USD. St. John and Tortola are both a little higher, with rentals as low as $95-$100USD, with the norm being closer to $150USD/night. Of course the sky’s the limit if you have the funds to do it, with rentals in all three places in the thousands of dollars per night.

This post is sponsored by Flipkey.  Flipkey is a great resource for finding rentals around the world. With over 10,000 properties in the Caribbean, FlipKey has great local options for indie travelers. FlipKey puts you in touch with vacation rental owners who can provide excellent local information and tips – not to mention good deals on lodging. They also provide travel tips and news on the FlipKey Blog.  

Photo credits:  Flipkey, Chaoleonard, Adam Seper, Ben Whitney