It's never too early to start planning a vacation. "Snowbird season" is still a couple of months away, but the best deals and the most-prime spots in tropical destinations are available right now. So-called "shoulder season," after summer vacation and before the winter high season, is actually the best time to book a holiday for November, December or January. The longer you wait, the less chance you will have of getting a prime spot at a reasonable rate.

If you can reserve early and find the right place, you can enjoy a high season vacation in the Caribbean without the crowds. Some of the region's best beachfront boutique hotels and private villas are ideal for enjoying a winter vacation without having to share your piece of paradise with the masses.


Because they provide privacy and luxury, even during the busiest season of the year, these hotels and resorts are highly prized by tourists. That is why you need to act early in order to reserve a place. You can also enhance your chances of avoiding the crowds by choosing islands that are more off-the-beaten-path. Some of the Caribbean's smaller nations have yet to be discovered by mainstream tourists. They are ideal for a privacy-filled getaway at any time of year.

The island of Anguilla is such a place. The Ani Villas, set on a cliff overlooking the sea, is ideal for a luxury-filled high-season vacation. These two villas are like self-contained resorts. The private pools, patios, tennis court, decks and concierge service mean that guests have pretty much whatever they want right at their fingertips. There is even a full range of water-sports equipment and a golf cart that guests can use to cruise around this uncrowded island.


Saint Barts is more popular than Anguilla, but it is known for its stylishness and is widely considered to be one of the coolest and most-pleasant islands in the entire region. Saint Barts is home to a number of private villas. One of the best is Manoir de Lurin. This five-bedroom estate is unique because it has three separate bungalows. So even if you book the villa with a group of people, you can each have your own private area, just like you would if you were staying on a large resort. Each bungalow is self-contained, with its own kitchen and facilities. Best of all, the Manoir is only a few footsteps from Gustavia, the main town on Saint Barts.


Private villas and resorts with bungalows are ideal for escaping the crowds during the high season in the Caribbean. Depending on how they are laid out, some resorts can give the same level of privacy as a private villa. Usually, the venues that can provide the best experiences are independent (not associated with a major hotel or resort chain). This is not always the case, but boutique resorts and privately-owned hotels are usually a much better choice if you want privacy and a unique experience.


One example of this type of venue is the Ladera Resort on Saint Lucia. The 32 suites here have open walls. This means that although there is another suite next to yours, there is a wall that separates your patio and private plunge pool from the neighbors. This means almost complete privacy even if you are outdoors.


And you will want to be outside at Ladera. The resort sits more than 1,000 feet above sea level. The private patio and open-air sitting area give guests some of the best views in the entire Caribbean. A spa, gym and "Serenity Garden" provide all the trappings of an upscale resort, while the concierge service and shuttle service can put all the best attractions of Saint Lucia at your fingertips.


Some of the most interesting independent hotels and resorts in the Caribbean might not bring over-the-top luxury, but they make up for it with utterly unique designs and atmosphere. One of the best examples of this type of venue is back on Saint Barts. Even the name of this place, La Banane, suggests a kind of offbeat appeal. The retro decor and bright color schemes are the first things that guests will notice. However, the covered living room, right next to the pool, is something very unique that everyone who stays here will enjoy. The lounge and bar area are also quite attractive, and the location, mere footsteps from the finest white sand beach on the island, is almost perfect.

Your turn

What is your ideal Caribbean accommodation option? Use the comments section to let us know where you prefer to stay during "snowbird season" in the West Indies.