Caribbean Boutique Hotels for Business Meetings and Executive Retreats

While the Caribbean is known for its beaches, luxury resorts and 5 Star hotels, it also has many secluded getaways with loyal guests that return year after year. Here are just a few of the properties that are ideal for small executive retreats and corporate events.


Jakes VillaJakes GuestroomJakes is a secluded south coast retreat. This cloistered haven of artistically designed oceanfront and gardenview cottages and villas has 60 guest rooms.

The Calabash Pavilion is the perfect setting for business meetings and private events.

Cooking, mosaic tile workshops and painting are just a few of the activities that are available on property for corporate team events.

Jakes is owned by the Henzell family. That name should be familiar as Perry Henzell was the Executive Producer and Director of the cult movie classic The Harder They Come starring Jimmy Cliff. The property is managed by Perry's widow Sally (it has been in her family since the 1940s) and their children.

Island Outpost

Island Outpost, owned by Island Records mogul Chris Blackwell (who was responsible for launching Bob Marley on the international arena), is a shimmering collection of unique hotels and resorts that are perfect for small groups.

Here is more detail about 2 of their properties, Goldeneye and Strawberry Hill.

  • Goldeneye

Goldeneye, which was the secret winter hideaway of James Bond creator Ian Fleming, has 17 guest rooms set in luxurious villas and cottages. Spacious living rooms are perfect for meetings and breakout groups. Tropical gardens, secluded coves, patios and private beaches. It's everything you need to add the wow factor to a small group retreat.

  • Strawberry Hill

In Jamaica's Blue Mountains, 3,100 feet above sea level, discover Strawberry Hill, a secluded retreat and favorite of celebrities from around the world. Strawberry Hill's 12 Georgian-style cottages with kitchenettes or fully equipped kitchens make it the perfect setting for small corporate groups seeking maximum privacy. Meetings can be held in The Gold Room. Then, groups can relax in The Library, at the spa, or in the gardens and verandahs that can be found throughout the property.


  • Ani Villas

Ani Villas' 2 adjacent fully staffed, 5 bedroom villas on a cliff offer breathtaking views of the Caribbean. Both properties have large living rooms that are perfect for meetings or relaxation. There are fabulous indoor and outdoor spaces for breakouts. The fully equipped gym, tennis, private pools, pool decks, and cliffside hot tubs provide the perfect setting for relaxation during downtime. Horse riding, cycling, snorkeling, scuba diving and deep sea fishing can easily be arranged.


  • Cocoa Cottages

I visited Cocoa Cottages when I was facilitating a workshop for a Bank in Dominica a few years ago. I was immediately impressed by the possibilities this off-the-beaten track cottage offered for small executive retreats. With 6 guest rooms, this secluded mountain retreat in a rainforest setting, is perfect for 5 participants and a facilitator. Meetings can take place outdoors or in the living room. The rainforest treehouse provides a unique meeting space for 6.

During downtime, you can tour attractions such as the Boiling Lake and Screw's Sulfur Spa or give canyoning, waterfall rappelling and abseiling a try.

The Bahamas


  • Compass Point

Originally developed and managed by Island Outpost, Compass Point's 15 pastel-colored huts are the perfect location for small executive teams seeking a secluded hideaway with all of the comforts of home. Rooms are equipped with DVD and CD players, surround sound stereo systems, microwaves and toaster ovens. Every room has a private, oceanview patio, balcony or porch.On property there is a beach, hot tub and freshwater pool.

Please check out earlier blog entries for more information about the Caribbean and hideaways in Jamaica, Barbados and Dominica.

Search the Cvent Boutique Hotels Directory for more properties in the Caribbean.

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