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Your Caribbean Island Guide

Your Caribbean Island Guide

Choosing a destination that makes everyone in your group happy can be tricky at times: one of you wants nightlife and surfing, while the other wants to relax on the beach in paradise. How do you narrow it down to just one island when there are so many to choose from?

We've collected our favorite types of trips and picked 14 Caribbean islands that excel above the others in those categories. Get inspired by our Caribbean guide, and choose the island that’s just right for you!

Which Caribbean Island is Perfect for You? 

Anguilla Anguilla for its Beaches

Suggested Villas:

Moonraker, 6 BR with pool

Infinity, 7 BR with pool

Anguilla has amazing beaches! Off the beaten path, it’s perfect for those who wish to relax and enjoy the beauty of the ocean.

1
 Bahamas Bahamas for Sailing

Suggested Villas:

Casa Plantation, 5 BR with pool

Villa Mouette, 3 BR with pool

The Bahamas have been called the "Sailing Capital of the World," and are great for both experienced and novice sailors.

2
 Barbados Barbados for Golf

Suggested Villas:

West Haven Villa, 4 BR Beachfront with pool

The Crowsnest, 3 BR and Beachfront

Ideal weather, world-class golf, Caribbean flavor and friendly locals attract many visitors to Barbados.

3
 Dominican Republic Dominican for Fun-Filled Nightlife

Suggested Villas:

Sunrise Villa, 8 BR Beachfront with pool

Villa Monaco, 4 BR with pool

This Island is alive with nightlife and casinos, we recommend the Dominican for Bachelor Parties and Spring Break Getaways.

4
 Jamaica Jamaica for its Staff

Suggested Villas:

Greatview, 6 BR with pool

Kaikala, 10 BR with pool

Most of our Jamaica villas come fully-staffed, which ensures a perfectly relaxing and carefree vacation!

5
 St. Barts St. Barts for Luxury & Privacy

Suggested Villas:

Delirium, 3 BR with pool

Villa K, 4 BR Beachfront with pool

Privacy and glamour are almost always guaranteed, this ultra-exclusive island manages to keep the masses away.

6
 St. Croix St. Croix for Scuba Diving

Suggested Villas:

Island Views, 2 BR with pool

Estate Belvedere, 6 BR with pool

St. Croix's tropical waters are inviting to Scuba Divers… with fun for both dive masters and beginners.

7
 St. John St. John for its Unspoiled Nature

Suggested Villas:

VI Friendship, 6 BR with pool

Presisio Del Mar, 6 BR Beachfront with pool

St. John is perfect for Nature Enthusiasts. Activities include hiking, kayaking, snorkeling, swimming and bird watching!

8
 St. Lucia St. Lucia for Romance

Suggested Villas:

Akasha, 4 BR with pool

Beau Rivage, 6 BR with pool

Fall in love all over again in St. Lucia. The glamorous scenery and dreamlike views make this island our most romantic destination.

9
St. Martin St. Martin for an Active Trip

Suggested Villas:

Vie En Bleu, 2 BR Beachfront with pool

L'Ecume des Jours, 4 BR Beachfront with pool

St. Martin is the island that truly has it all; casinos, a lively nightlife, two cultures to explore, and great restaurants.

10
St. Thomas St. Thomas for a Quick Getaway

Suggested Villas:

Star Garden, 5 BR with pool

Bliss, 3 BR with pool

St. Thomas is the lively center of the U.S. Virgin Islands and is a short-and-direct flight away from most American cities.

11
Tortola Tortola for Relaxation

Suggested Villas:

Aslantic House, 4 BR Beachfront with pool

Refuge, 3 BR Beachfront with pool

Escape the hustle and bustle to your own tranquil villa in Tortola! Tortola is a peaceful, beautiful and safe island.

12
Turks and Caicos Turks & Caicos for Snorkeling

Suggested Villas:

Amazing Grace, 5 BR Beachfront with pool

Villa Sublime, 3 BR with pool

Ideal for snorkeling and learning to scuba dive, Turks and Caicos' shallow turquoise waters are protected by a barrier reef.

13
Virgin Gorda Virgin Gorda for Wellness

Suggested Villas:

Sea's Song Villa, 3BR with pool

Amateras, 4 BR with pool

With wellness centers, spas, and private yoga classes, our Virgin Gorda villas offer complete mind & body relaxation.

14

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