Luxury Caribbean Vacations

18 Luxury Caribbean Vacations and the Best Thirdhome Properties

February 14, 2019 • By Caitlin Adams


Search Icon

Do you have a luxury Caribbean vacation on the mind but aren’t sure what island to choose for your next trip? Find inspiration below with recommendations on what to do on each Caribbean island and where to stay. All of the gorgeous properties below are part of THIRDHOME, the world’s most luxurious home exchange. Read below to find out what island is most your style, and get ready to start packing your swimsuit and sunglasses!

Luxury Caribbean vacations are available for the taking! Plan your trip today.

 Luxury Caribbean Vacations Anguilla


What to do: You’ll want to walk along the brilliant white-sand beach at Shoal Bay East and grab a cocktail at one of the laid-back bars that are scattered along the beach. If scuba diving is of interest to you, Prickly Pear Cays has an underwater cavern where you can dive by sunken shipwrecks.

Where to stay: Click here to view all THIRDHOME properties in Anguilla.


Luxury Caribbean Vacations Antigua

Antigua and Barbuda

What to do: Antigua is known for its picture-perfect beaches. Visit Half Moon Bay beach and bodysurf or snorkel. If you are a history enthusiast, Nelson’s Dockyard National Park was made a UNESCO World Heritage Site in 2016 and was once the Caribbean base of the British Royal Navy.

Where to stay: Reserve this spectacular 6-bedroom home with expansive ocean views or click here to view all THIRDHOME properties in Antigua and Barbuda.


Luxury Caribbean Vacations Aruba


What to do: Snorkel to view the USS Antilla shipwreck that has turned into an artificial reef, which means it is covered in bright coral and sea life. If you are feeling adventurous, take a hike through Arikok National Wildlife Park to a natural pool that is protected by limestone to break the waves of the ocean.

Where to stay: Stay in a tropical villa nestled on 3 private acres or click here to view all THIRDHOME properties in Aruba.


Luxury Caribbean Vacations Bahamas


What to do: If you are taking a family trip, visit Aquaventure Waterpark on Paradise Island and spend all day playing in the 141-acre waterpark. If you are looking for a more adult-oriented activity, go to Arawak Cay (in Nassau) over the weekends when they hold a big fish fry party complete with food, daiquiri bars and reggae music.

Where to stay: Enjoy a luxurious week at The Reef Atlantis or click here to view all THIRDHOME properties in the Bahamas.


Luxury Caribbean Vacations Barbados


What to do: For a leisurely stroll with beautiful views, walk along the boardwalk at Rockley Beach. Or, visit Paynes Bay Beach for particularly calm waters that are great for swimming.

Where to stay: Click here to view all THIRDHOME properties in Barbados.


Luxury Caribbean Vacations Cayman Islands

Cayman Islands

What to do: Two million tourists visit the Cayman Islands each year, making it an extremely popular spot for luxury Caribbean vacations. While visiting, make sure to take an afternoon to go to Starfish Point, where the calm waters protect thousands of starfish. You can easily spot them, so no snorkel gear is needed.

Where to stay: Click here to view all THIRDHOME properties in the Cayman Islands.


Luxury Caribbean Vacations Dominican Republic

Dominican Republic

What to do: Take a day trip to Peninsula de Samana for ample whale watching opportunities. For a slow-paced activity, relax on Playa Rincon, which is a gorgeous beach that has a thick palm forest on one side and the ocean on the other.

Where to stay: Spend a week in a beautiful 4-bedroom oceanfront villa or click here to view all THIRDHOME properties in the Dominican Republic.


Luxury Caribbean Vacations Guadeloupe


What to do: Guadeloupe is an archipelago of islands that all boast incredible natural beauty. You can visit dark-sand beaches on Place de Malendure or visit the traditional fishing village of Deshaies.

Where to stay: Vacation on a luxury catamaran yacht through THIRDHOME‘s Affiliation with TradeWinds.


Luxury Caribbean Vacations Jamaica


What to do: Hike up to Blue Mountain Peak just before sunrise for a view that will stick in your memory forever. Or, visit Kingston for a plate of jerk chicken and a nightlife scene full of unique culture. You can take multiple luxury Caribbean vacations here and still not get bored.

Where to stay: Enjoy complete privacy while staying in an estate home on 55 acres of lush property or click here to view all THIRDHOME properties in Jamaica.


Luxury Caribbean Vacations Puerto Rico

Puerto Rico

What to do: Take a walk down the vibrant and colorful streets of San Juan, which is the second-oldest European-founded settlement in the Americas. For a day at the beach, you can’t go wrong visiting Playa Flamenco, which stretches for a mile around a horseshoe-shaped bay.

Where to stay: Reserve a week at a resort property that directly overlooks a spectacular golf course or click here to view all THIRDHOME properties in Puerto Rico.


Luxury Caribbean Vacations St. John

St. John

What to do: Two-thirds of St. John is a protected national park, which makes this calm island a beautiful retreat for those who love nature. Snorkel with sea turtles at Caneel Bay, which is within Virgin Islands National Park.

Where to stay: Click here to view all THIRDHOME properties in St. John.


Luxury Caribbean Vacations St. Kitts

St. Kitts and Nevis

What to do: This two-island nation is perfect for a low-key vacation. Spend a day wandering through the Botanical Gardens of Nevis to see orchids, palms, water lily ponds, bamboo groves and more.

Where to stay: Resort-style living is waiting for you at this beach club or you can click here to view all THIRDHOME properties in St. Kitts and Nevis.


Luxury Caribbean Vacations St. Lucia

St. Lucia

What to do: The twin peaks of the Pitons make for perfect views, but a very challenging hike. If you are up for the challenge, you will be rewarded with expansive views of the island and ocean. For a more relaxing activity, visit the most famous beach on the island, Sugar Beach. It is situated between the two Pitons, which create unique views and an interesting beach experience. Many travelers take luxury Caribbean vacations to St. Lucia for its combination of rugged landscape and beautiful beaches.

Where to stay: Click here to view all THIRDHOME properties in St. Lucia.


Luxury Caribbean Vacations St. Maarten

St. Maarten

What to do: There is plenty to do in the Dutch side of this island, and Maho Beach is definitely a must-see experience. Maho Beach is famous for being adjacent to Princess Juliana International Airport, which means planes fly incredibly close to the beach as they are landing.

Where to stay: Stay in a condo that has beachfront access only steps away or click here to view all THIRDHOME properties in St. Maarten.


Luxury Caribbean Vacations St. Thomas

St. Thomas

What to do: St. Thomas is one of the most popular destinations for luxury Caribbean vacations, with visitors returning multiple times.  You won’t want to miss climbing up Blackbeard’s Castle, which was built in 1678, for harbor views. For a great beach experience, visit Magens Bay, which is packed with convenient amenities and has kayak rentals.

Where to stay: Bask in the sun at the Ritz-Carlton Destination Club or click here to view all THIRDHOME properties in St. Thomas.


Luxury Caribbean Vacations St. Vincent

St. Vincent and the Grenadines

What to do: This chain of islands is in the heart of the Caribbean Sea, and is ideal for those who want to avoid crowds while vacationing. For a relaxed beach experience, visit Saltwhistle Bay where there is a collection of beautiful beaches with a low-key vibe.

Where to stay: Click here to view all THIRDHOME properties in St. Vincent and the Grenadines.


Luxury Caribbean Vacations Trinidad and Tobago

Trinidad and Tobago

What to do: Visiting Trinidad and Tobago offers a very unique island experience. Visit the Port of Spain which has authentic restaurants, local markets and a multitude of bars and clubs. For an interesting daytime activity, book a cocoa-cultivation tour in Brasso Seco.

Where to stay: Click here to view all THIRDHOME properties in Trinidad and Tobago.


Luxury Caribbean Vacations Turks and Caicos

Turks and Caicos

What to do: Anyone who has taken a lot of luxury Caribbean vacations has most likely visited Turks and Caicos. These tropical isles are a piece of paradise and the crown-jewel beach to visit during your trip is Grace Bay Beach.

Where to stay: Click here to view all THIRDHOME properties in Turks and Caicos.


After seeing this list, how many luxury Caribbean vacations are you going to reserve this year with your THIRDHOME membership? When reserving your week in the Caribbean, keep in mind that our in-house concierge can help you Enhance Your Stay with arranging the activities we have mentioned in this article and more! 

Search our luxury travel blog

Search Icon

Hit ESC to close, ENTER to search