One of the most frequently asked questions I get almost daily in my inbox and DMs has got to be: “Where should we stay?” – A common and valid question. After all, where you end up staying during your Caribbean getaway, can have the potential to make or break your trip.

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The Caribbean is a popular vacation region and there are no shortages of accommodations to choose from. Sprawling resorts, Chic Boutique hotels, and lavish villas and condos are generously spread all over the islands. It’s enough to make your head spin when it comes to making a decision about where to stay.

This question is, in my opinion, also a very personal one. It really depends on which area you want to be in, what beaches you want to have nearby, whether you are renting a car or not, the reason for your visit, and of course your budget. You get the gist. It’s not a question that can be answered just like that and there is certainly no one-answer-fits-all reply to it either.

Obviously, I have my favorites. Spoiler Alert: I’m a boutique hotel/villa/chic condo kinda girl. But whatever you decide, you want to ensure your accommodation adds to the magic of your trip. So, let’s unravel the accommodation types available on the Caribbean islands and find out what suits you best.

1. Boutique Hotels: Where Elegance Meets Charm

Boutique hotels are your cozy hideaways, offering a warm, personalized, and intimate experience that larger establishments usually lack. If you crave a unique ambiance, and personalized service, with usually a dash of chicness included, then a Boutique Hotel might be perfect for you. Boutique hotels are the go-to choice for travelers who cherish individuality and a touch of local charm.

Two of my favorite boutique hotels in St. Martin are Le Petit Hotel and L’Esplanade Hotel. Mention TTIG and get a 5% discount on your stay.

Best Suited for:

  • Couples looking for a romantic escape.
  • Solo travelers seeking a more intimate experience.


  • Personalized Service: You’re not just a guest; you’re family in boutique hotels.
  • Unique Ambiance: Each boutique hotel has its own character, making every stay distinct.
  • Local Touch: Often, they provide a more immersive experience into the local culture.


  • Limited Amenities: Boutique hotels are cozier, so don’t expect massive pools or multiple restaurants.
  • Varied Pricing: Prices can vary widely from one boutique hotel to another.

2. Vacation Rentals: Your Home Away from Home

If you’re the type of traveler who yearns for that sense of home, vacation rentals are tailor-made for you. These accommodations offer affordability and independence, making them an excellent choice for families, groups, and those who want to explore the Caribbean at their own pace. Vacation rentals are like a blank canvas for your Caribbean adventure.

Best Suited for:

  • Families with children needing space and flexibility.
  • Groups of friends looking for a cost-effective option.
  • Travelers who enjoy cooking their meals and living like locals.


  • Affordable: Vacation rentals offer various price points, making them suitable for travelers on different budgets.
  • Local Experience: Live like a local and discover hidden gems known only to the residents.
  • Space and Comfort: Enjoy the perks of a full kitchen, extra bedrooms, and more space to relax.


  • Quality: The quality of vacation rentals can differ greatly, so do your research.
  • Limited Services: You won’t have a concierge at your beck and call, but you’ll have freedom.
  • Location Hurdles: Vacation rentals are often located in residential areas and you will most often need a car to be able to get to and from the rental.

3. Villas: Luxury Living in the Caribbean

For those who seek the ultimate in luxury and privacy, villas are the epitome of opulent living. They’re designed for travelers who want to bask in their private paradise, complete with breathtaking views, exceptional amenities, and the freedom to tailor their experience to their heart’s desire.

Staying in a villa means Luxurious Freedom. Search for the best St. Martin and Caribbean Villas from my good friends at Top Villas here.

Best Suited for:

  • Luxury individuals.
  • Larger families or groups celebrating special occasions.
  • Anyone willing to splurge for an unforgettable Caribbean getaway.


  • Privacy and Space: Villas are perfect for families or groups of friends looking to enjoy a private getaway. Villas are especially recommended when you’re celebrating something epic in the Caribbean.
  • Amenities Galore: Think private pools, stunning views, and often, a personal chef or concierge.
  • Customizable: You can tailor your stay to your exact preferences.


  • Pricey: Luxury comes at a price, but it’s worth it for a grand escape.
  • Isolation: If you’re looking for a buzzing atmosphere, you might feel a bit cut off.

4. Resorts: Where Caribbean dreams are born

For those who want to be pampered from dawn to dusk, beachfront resorts are the way to go. These sprawling properties offer a seamless blend of convenience, prime locations, and activities for all ages. Whether you’re celebrating a special occasion, honeymooning, or simply seeking ultimate relaxation, beachfront resorts are tailored for travelers who want it all in one.

Best Suited for:

  • Honeymooners seeking romance.
  • Families looking for fun.
  • Travelers who are looking for convenience.


  • Prime Locations: Waking up to the sound of waves just outside your window? Priceless.
  • Amenities: Resorts offer everything from lavish pools to fine dining, activities, and in-room services.
  • Convenience: Many excursions and activities can be arranged right at the resort.


  • Pricey: Resorts can come with a hefty price tag.
  • Crowded: Popular resorts can get a bit packed during high season.
  • Less Local Flavor: You might miss out on experiencing the authentic Caribbean culture. So make sure to add some offsite activities to your itinerary.

In Conclusion

Ultimately, the best type of accommodation for your Caribbean adventure depends on your preferences and priorities. If you’re like me, you’ll love boutique hotels for their unique charm and personalized service. However, Airbnb and villas offer different flavors of the Caribbean experience, perfect for those who appreciate affordability and privacy.

Remember to explore your options, read reviews, and, if you’re considering Airbnb or villas, communicate with your host or property manager to ensure your needs are met.

If you have questions about your upcoming Caribbean getaway, like where to stay on the islands of St. Maarten, Anguilla, Statia, or Saba, jump on a call with me and let me answer all your questions and take the stress of planning out of your hands. Click here to book a Zoom Call with me.

No matter where you choose to stay, the Caribbean islands have a warm welcome waiting for you. Enjoy your island adventure, and may your accommodation choice be the cherry on top of an already incredible experience!

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