Caribbean STR Blog

Investment insights for the Caribbean & coast

Market comparisons, tax incentives, and underwriting strategy for short-term rental investors.

Outer Banks NC · June 18, 2026

The Outer Banks: The Risk vs. Reward of STR Investment

The Outer Banks is the most established STR market in North Carolina — and also one of the most exposed to hurricane, insurance, and erosion risk. Here's how to weigh both sides honestly.

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Carolina Beach NC · June 10, 2026

What's a Realistic Cap Rate for a Carolina Beach Vacation Rental?

Cap rate headlines for coastal NC properties get thrown around loosely. Here's how to calculate a realistic number for a Carolina Beach STR, and what's actually driving it.

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Underwriting Fundamentals · June 9, 2026

Cash-on-Cash Return vs. Cap Rate: Which Number Should You Actually Trust?

Two investors can look at the same STR listing and walk away with completely different numbers in their head — because they're answering two different questions. Here's what each metric actually tells you, and when to lean on which one.

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Dominican Republic · May 12, 2026

CONFOTUR Explained: The Tax Break Dominican Republic STR Investors Are Missing

CONFOTUR can exempt a Dominican Republic short-term rental from property tax, transfer tax, and import duties for up to 15 years. Here's how it actually works and who qualifies.

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Market Comparison · April 28, 2026

Aruba vs. Dominican Republic: Where Should You Buy an STR in 2026?

Both are Caribbean STR powerhouses, but they reward very different investment strategies. Here's how the two markets actually compare on revenue, regulation, and risk.

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