Hotels charge extra for overwater bungalows, but I prefer these. You have a beach right outside your door.

Windward Islands beach rentals

We found 80 beach rentals — enter your dates for availability

Where to?

Dates

Calendar
Flexible dates

December 2025

14

January 2026

Find spaces that suit your style

House

Condo/Apartment

Beach Rentals in Windward Islands

Holiday Rental options in Windward Islands

Holiday rentals with pool in Windward Islands
Standard Link for Windward Islands
Holiday rentals with spa pool in Windward Islands
Standard Link for Windward Islands
Mountain holiday rentals in Windward Islands
Standard Link for Windward Islands
Ski holiday rentals in Windward Islands
Standard Link for Windward Islands
Lake holiday rentals in Windward Islands
Standard Link for Windward Islands
Pet-friendly holiday rentals in Windward Islands
Standard Link for Windward Islands
Family-friendly holiday rentals in Windward Islands
Standard Link for Windward Islands
Oceanfront holiday rentals in Windward Islands
Standard Link for Windward Islands

Rental Ideas

More Holiday Rentals ideas

People also search for

e95b8b4e-056c-1e45-1a29-8fa24e98215445df4e29-d3ad-43fe-a955-dd4ed44ee752